Windham, ME Vacation Rentals

Explore 109 vacation rentals, homes, and villas in Windham, ME for your next getaway or business trip. Experience the privacy of a home with premium amenities such as Air Condition Homes, Homes with Free Parking and Best Affordable Homes, designed for a more comfortable and convenient stay. Every home is curated and professionally managed, with 24/7 local support, high-speed Wi-Fi, and premium linens included. With homes starting as low as $143 per night and featuring up to 8 bedrooms and 8 bathrooms, there's an option for every trip, from family vacations and group getaways to extended stays. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can also earn and redeem points on every booking.

109 Vacation Rentals in Windham

Falmouth Vacation Rental On Highland Lake!

Windham, ME, US
2 Bedrooms 4 Guests
Sep 28 - 30
$169 night

Travel to this charming Falmouth vacation rental and spend your days relaxing in and by Highland Lake! This 2-bedroom, 1-bathroom home is the perfect place to book for you and your little ones. On lake days, take the stand up paddle boards for a spin or just dive into the water and enjoy spending time with your family in the water. When you want to explore, check out nearby walking trails and wildlife, or go into town to check out the Children's Museum & Theatre of Maine! -- THE PROPERTY -- STR22-00067 | 1,300 Sq Ft | On-Site Lake Access | 2 Stand Up Paddle Boards | In-Unit Laundry Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds HOME HIGHLIGHTS: Living room, dining table, Smart TVs, board games, laptop-friendly workspace, 2 kayaks, beach chairs & towels, life vests KITCHEN: Cooking basics & spices, fridge, stove/oven, Crockpot, microwave, dishwasher, coffee grinder & maker, toaster, blender, trash bags/paper towels GENERAL: Free WiFi, washer/dryer, linens/towels, ceiling fans, brand new furnace, window A/C units, hangers, hair dryer, iron/board FAQ: 1 step required for access, single-story home, grab rails in shower PARKING: Garage (2 vehicles), driveway (2 vehicles) -- THE LOCATION -- LAKE DAYS: Highland Lake (on-site access), Broad Cove Reserve (13 miles), Higgins Beach (17 miles), Pine Point Beach (19 miles) THINGS TO DO: Prides Corner Drive-In (3 miles), Riverside Golf Course (5 miles), Sunset Ridge Golf Links (6 miles), Portland Museum of Art (9 miles), Children's Museum & Theatre of Maine (9 miles) OUTDOOR RECREATION: The Presumpscot Regional Land Trust (7 miles), Presumpscot Falls Park (7 miles), Capisic Park Pond (8 miles), Brooklawn Memorial Park (9 miles), Thomas Knight Park (11 miles) NEARBY CITIES: Westbrook (7 miles), Portland (11 miles), Old Port (12 miles) AIRPORTS: Portland International Jetport (10 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story home requires 1 step for access - NOTE: The property's previous water pressure issues have been fully resolved

Private 2BR waterfront home, hot tub, pool table, sandy beach, BBQ, w/d, wifi

Scarborough, ME, US
2 Bedrooms 4 Guests
Aug 26 - 28
$262 night

Escape to this charming house located on a serene 10-acre pond in Scarborough, ME, offering a private sandy beach and stunning lake views. This year-round retreat features a luxurious hot tub and a fun pool table, ensuring endless entertainment for guests of all ages. Step outside onto the deck to enjoy the peaceful surroundings, or fire up the gas grill for a delightful cookout by the water. Inside, the home boasts a fully equipped kitchen with modern appliances, a cozy living room, and comfortable bedrooms including a king and queen bed. With amenities like a washer/dryer, internet access, and Netflix streaming, this home provides all the comforts you need for a relaxing stay. Explore the local area and enjoy activities such as swimming, hiking, and bird watching, or simply unwind and take in the picturesque views of the pond. Conveniently located within a 15-minute drive to the beautiful Scarborough ocean beaches and downtown Portland. Enjoy nearby local restaurants, shops, and entertainment options, this house is the perfect base for your Maine getaway. Whether you’re seeking adventure, relaxation, or family fun, this lakefront retreat offers something for everyone. Book your stay now and create unforgettable memories in this idyllic setting by the water. Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Fireplace is not for guest use.

Frye Island Family Cabin with Lake & Beach Access!

Standish, ME, US
2 Bedrooms 8 Guests
Aug 29 - 31
$218 night

Experience the beauty of Frye Island from this charming 2-bedroom, 1.5-bath vacation rental with a loft. Nestled in a peaceful setting, this private, spacious cabin offers a quiet deck for soaking up the sun and an outdoor dining area for al fresco meals. Walk to and explore the island's attractions, like the recreation center and Frye Island Beach 6. This cozy cabin is the perfect retreat for families and friends looking to create unforgettable memories on Frye Island. Book your stay today! -- THE PROPERTY -- Dog Friendly w/ Fee | Walk to Beaches | Free Community Amenities Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Loft: Queen Bed, Twin Bed, Twin Sleeper Sofa COMMUNITY AMENITIES: Pool, basketball court, tennis court, beach club, rec center, racquetball, fitness center (fee paid on-site) INDOOR LIVING: Open layout, beamed ceilings, Smart TVs, DVD player, group-friendly dining table, breakfast bar w/ seating OUTDOOR LIVING: Beach chairs, gas grill, fire pit w/ outdoor seating, large private deck, outdoor dining area, unfenced backyard KITCHEN: Cooking basics, coffee maker, dishwasher, stove/oven, refrigerator, microwave, ice maker, spices, dishware & flatware, hot water pot, toaster, Crockpot GENERAL: Free WiFi, linens & towels, electric heating, window A/C units, in-unit washer & dryer, laundry detergent, hair dryer, iron/board, trash bags & paper towels FAQ: Pet fee (paid pre-trip), stairs required for access PARKING: Driveway (6 vehicles), RV/trailer parking available on-site -- THE LOCATION -- LOCAL ATTRACTIONS: Frye Island Beach 6 (0.3 miles), Frye Island Ferry (1 mile), 14 private beaches, 2 boat launches, marina, waterfront restaurants ADVENTURE TIME: Sebago Trails Paddling Company (9 miles), Naples Seaplane Adventures (12 miles), Maine Day Ventures/formerly Maine Foodie Tours (30 miles) TEE TIME: Frye Island Golf Club (0.6 miles), Point Sebago Golf Course (9 miles), Sunset Ridge Golf Links (24 miles), Riverside Golf Course (25 miles) AIRPORT: Portland International Jetport (30 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly with a $50 fee (+ fees & taxes, dogs only, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This property requires stairs to access the main living area and additional stairs to access the loft sleeping area - NOTE: Community amenities are available free of charge, with the exception of the fitness center which can be paid for on-site. No access code is required to access the other community amenities

2 Mi to Marina & Beach: Frye Island Retreat!

Standish, ME, US
1 Bedrooms 8 Guests
Aug 22 - 25
night

Dogs Welcome w/ Fee | Seasonal Island Getaway | Community Pool Plan a summer to remember on beautiful Frye Island! Only accessible by ferry, this rustic 1-bedroom + loft, 1-bathroom vacation rental promises a relaxing setting you can't find anywhere else. After coffee on the cabin's covered porch, head to the marina to launch the boat and spend sunny afternoons cruising the wake of Sebago Lake. In the evening, stop by the community clubhouse for a cocktail or cozy up around a crackling fire! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom: 1 king bed - Loft: 4 full beds - Living Room: 1 queen sleeper sofa COMMUNITY AMENITIES - Seasonal outdoor pool (not heated) - Beach access - Community center, cafe - Tennis courts, golf course (addt'l fee paid on-site) INDOOR LIVING - Flat-screen TV - Open floor plan - Dining table OUTDOOR LIVING - Covered porch, outdoor seating - Gas grill (propane provided) - Wood-burning fire pit - 2 golf carts (waiver may be required) KITCHEN - Refrigerator, stove/oven - Keurig coffee maker, French press, toaster, microwave - Cooking basics, dishware & flatware GENERAL - Free WiFi, keyless entry - Mini-split A/C & heating, ceiling fans - Washer & dryer - Linens & towels, trash bags & paper towels FAQ - Pet fee (paid pre-trip) ACCESSIBILITY - 5 exterior steps required for entry - 2-story cabin - Bedroom/bathroom on 1st floor PARKING - Driveway (3 vehicles) - Trailer parking available on-site -- THE LOCATION -- - Island getaway on Frye Island w/ access to Sebago Lake’s top attractions - 1 mile to Frye Island Ferry Dock - 2 miles to Frye Island Marina - 9 miles to Raymond: shops & dining - 11 miles to Sebago Lake State Park - 38 miles to Portland International Jetport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $50 fee (+ fees & taxes, dogs only, 2 max) - No events, parties, or large gatherings - Must be at least 18 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story cabin requires 5 steps to enter. The bedroom and bathroom are located on the 1st floor - This property runs on a septic system - A waiver may be required prior to using the golf cart - The community golf course requires an additional fee, which can be paid on-site

Near Portland Trails: Walkable Apartment w/ Deck

Portland, ME, US
1 Bedrooms 4 Guests
Aug 17 - 20
night

Open Layout | In-Unit Laundry | 1/2 Mi to Restaurant & Market | BBQ Ready Discover Portland, ME, like a local at this 1-bedroom, 1-bath vacation rental. Step outside to hike or bike along scenic trails, grab lunch in town, and finish your afternoon with a craft brew. For more excitement, stroll through the cobblestone streets of Old Port and immerse yourself in its vibrant waterfront dining scene. This apartment is perfect for outdoor adventurers — it's a hidden gem you don't want to miss! -- THE PROPERTY -- STHR-005962-2024 SLEEPING ARRANGEMENTS - Bedroom: 1 queen bed - Living Room: 1 full sleeper sofa MAIN FEATURES - Furnished deck, outdoor dining area, gas grill - 2 Smart TVs - Private deck - Breakfast bar KITCHEN  - Stove/oven, refrigerator, dishwasher - Microwave, toaster oven - Drip coffee maker & Keurig (coffee provided) - Cooking basics - Dishware/flatware - Trash bags & paper towels GENERAL  - Free WiFi - Washer & dryer - Central A/C & heating, ceiling fan - Linens/towels, complimentary toiletries - Iron/board, hair dryer - Keyless entry FAQ - Homeowner on-site (separate unit) ACCESSIBILITY - Single-story apartment, 3 steps to enter PARKING - Driveway (2 vehicles) -- THE LOCATION -- - 0.5 miles to Back Cove - 1 mile to Portland's downtown area: bars, cafes, coffee shops, restaurants & boutiques - 1 mile to Payson Park & Payson Hill Winter Recreation Area - 4 miles to Mackworth Island State Park - 4 miles to Portland Int'l Jetport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This single-story apartment requires 3 steps to enter - The homeowner lives on-site, in a completely separate unit, and may be present during your stay

Waterfront Access with Kayaks, Private Deck and a Firepit

Gray, ME, US
4 Bedrooms 13 Guests
Aug 22 - 29
$724 night

Escape to this spacious, serene cabin with modern amenities on Little Sebago Lake. Includes 4 bedrooms, 7 beds & 2 living room areas. Enjoy a luxe retreat into nature with Kayaks, Paddle Boards, a Firepit, BBQ grill, and a spacious private deck with a table and seating. Just steps away from two waterfront access points. Massive windows in the living / dining room bring in lots of natural light. Fully-equipped kitchen plus a dining room table to enjoy a shared meal after a day of adventuring. HIGHLIGHTS: ★ On Little Sebago Lake - great for swimming, fishing, sunbathing & water activities ★ 4 Bedrooms, 7 Beds ★ Walk to a neighborhood lake access points ★ 2 Kayaks and 2 Paddle Boards provided ★ Massive private deck with an outdoor dining table that seats 8 ★ Dining room + table that can seat 6 ★ Bonus living room downstairs with a bar, mini fridge and smart TV ★ Dedicated workspace with a desk, chair & printer ★ High chair and pack-n-play available for children ★ Board Games + Books ★ Outdoor firepit with seating available - please note, we do not provide wood ★ Gas BBQ grill - please note, we do not provide propane for the grill ★ Plenty of storage for your clothing and other items ★ Hassle-free check-in with no keys, just codes ★ Coffee + Coffee Maker ★ Plenty of parking for your cars ★ High-speed Wifi ★ Shampoos, conditioner and body wash provided ★ Washer/Dryer ★ 12 minutes from Fisherman’s Net - a fish market/deli that is top rated in the area. You can get some delicious fresh seafood and lobster there. ★ Just 30 minutes to Portland or Freeport for shopping and dining BEDS: Bedroom 1: King Bed Bedroom 2: King Bed Bedroom 3: Double Bed Bedroom 4: Queen Bed + Twin-over-Full Bunk Beds Basement Living Room: Queen Sleeper Sofa BATHROOM Bathroom 1: Full size with standing shower Bathroom 2: Full size with shower/tub combo Located on the shores of Little Sebago Lake, a scenic freshwater lake located in southern Maine in the town of Gray. Gray is a charming and tranquil town nestled in the heart of southern Maine, offering a perfect blend of natural beauty and small-town charm. Our neighborhood is a peaceful retreat surrounded by picturesque landscapes, yet conveniently located with easy access to modern amenities and attractions. The area is known for its beautiful scenery, featuring lush forests, serene lakes, and rolling hills. Just steps away from our home, you can explore Little Sebago Lake, perfect for boating, fishing, swimming, and kayaking. For hiking enthusiasts, the Libby Hill Forest Trails offer miles of well-maintained trails through diverse woodlands. Nearby Attractions: - Maine Wildlife Park: A short drive away, this park is home to a variety of native wildlife, offering a unique and educational experience for all ages. - Pineland Farms: Located nearby, this working farm and educational center provides opportunities for horseback riding, hiking, and farm-to-table dining experiences. - Gray Plaza Shopping Center: For your convenience, find grocery stores, cafes, and local shops within a short drive. -Bittersweet Ridge Disc Golf: Enjoy a day outdoors at Bittersweet Ridge Disc Golf. About a 20 minute drive from the house. -Naples Seaplane Adventures - Exciting scenic flights over the lakes and mountains of Western Maine. A fun adventure for the entire family. About a 30 minute drive from the house. -Dingley’s Wharf - #1 in the area for Boat Tours & Water Sports Waterskiing & Jet-skiing, Gear Rentals, Boat Rentals, Stand Up Paddle boarding and Kayaking & Canoeing. About a 30 minute drive from the house. -Seacoast Adventures - A seasonal, outdoor fun center with mini-golf, go-karts & a 100-ft. sky swing. About a 15 minute drive from the house. -Point Sebago Golf Resort - About a 20 minute drive from the house. -Steamboat Landing Mini Golf - Enjoy playing mini golf with the family. About a 30 minute drive from the house. -Fisherman’s Net - A fish market/deli that is about a 12 minute drive from the house. It’s top rated in the area. You can get some delicious fresh seafood and lobster there. Nearby Cities: - Portland: Approximately a 30-minute drive, offering a vibrant cultural scene, historic sites, and waterfront dining. - Freeport: About a 30-minute drive, home to the famous L.L. Bean flagship store and numerous outlet shops. You’ll have the entire house to yourself. We also provide 2 kayaks and 2 paddle boards you can use as well as paddles & 4 life jackets, located in the shed. Kayaks & canoes found at the shared beaches belong to other homeowners, and are not to be used. Please message me via the app and I’ll be happy to help! Our home is located on the shores of Little Sebago Lake, a scenic freshwater lake located in southern Maine in the town of Gray. You can walk from our house to two different private neighborhood lakeshore access points. The town of Gray is charming and tranquil, nestled in the heart of southern Maine. Our neighborhood is a peaceful retreat surrounded by nature, yet conveniently located with easy access to modern amenities and attractions. The area is known for its beautiful scenery, featuring lush forests, serene lakes, and rolling hills. Just steps away from our home, you can explore Little Sebago Lake, perfect for boating, fishing, swimming, and kayaking. For hiking enthusiasts, the Libby Hill Forest Trails offer miles of well-maintained trails through diverse woodlands. We sit up high above other houses in the neighborhood. This gives you a beautiful view but presents a potentially challenging driveway for compact or low clearance vehicles. There is enough space for 4-5 cars at the top of our driveway but if your vehicle has a low ground clearance you may park at the bottom of the driveway as long as more than half of your vehicle is off of the street. There is a grassy spot to the left of our driveway, and another at the bottom of the stairs that lead down to the street. There is a staircase up to the house from the road. DO NOT PARK PAST THE NO PARKING SIGN next to the staircase at the bottom of the driveway as that is the neighbors property and parking area. From the house, we are about a 2-3 minute walk to one lake access point. You walk down the stair case, take a right down Qualey Road to where the gravel road meets the pavement. Then turn left to walk to the lake. This area has great access for kayaks & paddle boards. There is a second lake access point that is about a 6 minute walk. This is where Qualey Road meets Mountain View Road. This area is great for swimming. Kayak and paddle access is also allowed here. The house has two different ways to heat/cool the house. Split units are located on all 3 levels of house. They control the air and heat in Thermostats on the walls only control the heaters on that floor - these are not necessary to use unless the house is very cold in the winter. The two bedrooms off of the kitchen do not have ac in them- the split units in the living room keep them cool. If extra air is needed, there are AC floor units in the closets that can be used if needed. Guests would have to put the duct into the window to create air flow. Driveway: We sit up high above other houses in the neighborhood. This gives you a beautiful view but presents a potentially challenging driveway for compact or low clearance vehicles. There is enough space for 4-5 cars at the top of our driveway but if your vehicle has a low ground clearance you may park at the bottom of the driveway as long as more than half of your vehicle is off of the street. There is a grassy spot to the left of our driveway, and another at the bottom of the stairs that lead down to the street. There is a staircase up to the house from the road. DO NOT PARK PAST THE NO PARKING SIGN next to the staircase at the bottom of the driveway as that is the neighbors property and parking area.

Serene Coastal Home with Private Beach Access, Hot Tub, and Spacious Decks

Cumberland Foreside, ME, US
4 Bedrooms 8 Guests
Aug 16 - 18
$618 night

Serene Coastal Retreat with Beach Access & – Cumberland Foreside, ME Escape to your tranquil Maine getaway in this stunning modern home, just a five-minute walk from private deeded beach access. Thoughtfully designed and meticulously maintained, this spacious retreat offers the perfect balance of comfort, style, and coastal charm. Relax in the airy living room with a cozy hearth, or step out onto the sunny deck to enjoy morning coffee or evening conversations surrounded by nature. The open-concept kitchen features a large island and flows seamlessly to a deck overlooking the woodland patio and hot tub—ideal for entertaining family and friends. The private Primary Suite wing is a true sanctuary, complete with its own staircase, ensuite bathroom with heated floors and a soaking tub, and a sun deck to soak in the peaceful surroundings. Additional spaces include a screened-in porch, a sun-drenched sunroom, and multiple patios and decks for effortless indoor-outdoor living. The finished walkout basement with a full bath offers extra space for guests, while central air and mini-splits ensure year-round comfort. Enjoy access to Broad Sound for kayaking, swimming, or picnics. Explore nearby trails, preserves, and beaches, or visit the charming shops of Falmouth Foreside. With quick access to Portland and I-95, this home is a perfect coastal escape for families or friends. Things to know: Occupancy Notice: Maximum 8 guests. Local rules allow up to 5 unrelated guests, or more if from the same family.The hot tub is currently down for maintenance but will be back up soon. (7/20/26) Book your stay today and immerse yourself in Maine’s serene coastal lifestyle!

Renovated condo with prime West End location, 2 en suite bathrooms, & HGTV style

Portland, ME, US
2 Bedrooms 4 Guests
Aug 23 - 25
$432 night

Portland ME STR License: 20180761-ST Surround yourself with historic homes, tree-lined streets, and some of the best restaurants and cafes in the city when you escape to this beautifully renovated condo in Portland’s West End. Revel in the century-old mansions nearby and the clapboard-sided homes famed architect John Calvin Stevens designed around the turn of the century. This second-story condo is part of a gorgeous old building that dates back to the 19th century. On this quiet street in a neighborhood renowned for its old-world charm, you can leave your car in one dedicated parking space and get around entirely on foot. The historic Old Port is only a few minutes away by Uber or car. Many of Portland’s tastiest restaurants are within walking distance, so you’ll always have delicious options. The Western Promenade overlooking the Fore River and Commercial Street are also within strolling distance. Indulge your creative side at the Portland Museum of Art or the Maine College of Art, which are less accessible on foot. Relax at the Nine Stones Spa, then try one of the many breweries or bars as the evening approaches for a refreshing drink. Ride the Casco Bay ferry before returning to your vacation home for an even more scenic way to view Portland. While the building dates back to the late 1800s, the condo was thoughtfully redesigned to give it a bright, airy, and modern feel. Throughout the space, you’ll find wood floors, oversized windows, granite countertops, stainless steel appliances, and custom cabinetry in the kitchen and bathrooms. The modern heat pump system for heating and cooling ensures you’ll have your ideal temperature. After a day spent visiting the Portland Head Light, come home to a polished living room with a TV providing local and national television, a well-equipped kitchen, and such home conveniences as a stacked washer/dryer and complimentary high-speed WiFi. Each bedroom has a TV offering the same programming as that found in the living room, en suite bathroom sporting tiled showers with frameless shower doors, and remote-controlled air-conditioning, giving everyone the privacy and comfort they crave. Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. Streaming services are available with guests’ own accounts. This condo is in a multi-unit building where you will hear the occasional neighboring sounds. All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises.

Gorgeously renovated, 2-condo property in the West End - walk everywhere

Portland, ME, US
4 Bedrooms 8 Guests
Aug 23 - 25
$926 night

Portland ME STR License: 20180761-ST Find the perfect Portland setting for a group of friends or several couples at this beautifully renovated, two-condo property in the heart of the historic West End. Revel in the century-old mansions nearby and the clapboard-sided homes famed architect John Calvin Stevens designed around the turn of the century. This property comprises two of the four condos in a gorgeous old building that dates back to the 19th century. On this quiet street in a neighborhood renowned for its old-world charm, you can leave your cars in two dedicated parking spaces and get around entirely on foot. The historic Old Port is only a few minutes away by Uber or car. Many of Portland’s tastiest restaurants are also a mere 15-minute walk away at most, meaning you’ll always have delicious options at your disposal. The Western Promenade overlooking the Fore River, and Commercial Street are all within strolling distance as well. Indulge your creative side at the Portland Museum of Art or the Maine College of Art less than 10 minutes away on foot. Relax at the Nine Stones Spa, then try one of the many breweries or bars as the evening approaches for a refreshing drink. For an even more scenic way to view Portland, take a ride on the Casco Bay ferry before heading back to your vacation home. While the building dates back to the late 1800s, the condos were thoughtfully redesigned in 2014 to give each a bright, airy, and modern feel. Both spaces feature hardwood floors, granite countertops, custom cabinetry in the kitchen and bathrooms, oversize windows, and stainless steel appliances. The modern heat pump system for heating and cooling ensures you’ll always have your ideal temperature available to you. After a day spent taking the ferry to Peaks Island or dining your way across Portland, come home to two separate condos that give everyone the space they desire. Each condo offers its own living room with a TV providing local and national television, a well-equipped kitchen, two bedrooms, and a stacked washer/dryer. In every bedroom, you’ll find an en suite bathroom sporting tiled showers with frameless shower doors, a TV offering the same programming as that found in the living room, and remote-controlled AC, giving everyone there unparalleled privacy and comfort. Complimentary high-speed WiFi is provided. Things to Know Check-in time: 4:00 p.m. Check-out time: 10:00 a.m. All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m. No smoking is permitted anywhere on the premises. Streaming services are available with guests’ own account credentials.

Spacious Portland Home: Walk Downtown!

Portland, ME, US
3 Bedrooms 6 Guests
Aug 16 - 18
$1,251 night

Experience coastal city living like a local with a stay at this 3-bedroom, 2.5-bath vacation rental in Portland, Maine. This home offers a comfortable interior with free WiFi, a full kitchen, a rooftop deck with ocean views, and a location within walking distance of the Old Port shops, restaurants, and the Portland waterfront area. While you’re in town, be sure to take a stroll through historic Fort Allen Park, visit the Eastern Promenade, or watch the sunrise at East End Beach. -- THE PROPERTY -- STHR-005145-2023 | Walkable Location | In-Unit Elevator | Near Ferry Terminal Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Living Room: Sleeper Sofa INDOOR LIVING: Smart TVs, heated bathroom floors, dining table, books, board games, ceiling fans, bar area w/ wine fridge, computer workspace KITCHEN: Blender, coffee maker, cooking utensils, Crockpot, dishware & flatware, dishwasher, ice maker, microwave, spices, toaster oven, wine glasses OUTDOOR LIVING: Rooftop deck, ocean views, patio w/ gas grill GENERAL: Free WiFi, keyless entry, heat & A/C pumps, complimentary toiletries, hair dryers, hangers, in-unit laundry machines, iron/board, linens/towels, trash bags/paper towels FAQ: 2 steps required to enter, elevator access, Ring Doorbell (facing out), no EV charging on-site PARKING: Garage (1 small vehicle), street parking (1 hour/day Mon-Sat), nearby public parking lots -- THE LOCATION -- DOWNTOWN PORTLAND (~0.4 miles): Shopping, restaurants; Eventide Oyster Co., The Highroller Lobster Co., Merrill Auditorium, Cross Insurance Arena, Portland Museum of Art, Monument Square OPT OUTSIDE: Casco Bay Lines Ferry Terminal (0.3 miles), Lincoln Park (0.3 miles), Eastern Promenade Trail (0.5 miles), Fort Allen Park (0.8 miles), Bayside Trail (1 mile), East End Beach (1 mile), Willard Beach (4 miles), Bug Light Park (5 miles), Portland Head Light (6 miles) LOCAL BREWS: Shipyard Brewing Company (0.2 miles), Liquid Riot Bottling Company (0.6 miles), Rising Tide Brewing Company (0.7 miles), Batson River Brewing & Distilling -- Portland (1 mile) AIRPORT: Portland International Jetport (5 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires 2 steps to enter. Stairs are present throughout the home, but an in-unit elevator is available to avoid most of those stairs - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera. The camera is located on the rooftop patio facing the ship ladder that leads to the upper roof area and does not look into any interior spaces. The camera actively records video when motion is detected by the device Licence number: STHR-005145-2023;STHR-005145-2023;STHR-005145-2023

Historical & dog-friendly West End condo with parking - walk to all of Portland

Portland, ME, US
2 Bedrooms 4 Guests
Aug 18 - 20
$432 night

Portland ME STR License: 20180761-ST Experience a quintessential Portland setting in the city’s most desirable neighborhood at this beautifully renovated condo in the heart of the historic West End. Revel in the century-old mansions nearby and the clapboard-sided homes famed architect John Calvin Stevens designed around the turn of the century. Perfect for couples traveling together, this condo features an all-suite layout is part of a gorgeous old building that dates back to the 19th century. On this quiet street in a neighborhood renowned for its old-world charm, leave your car in a dedicated parking space and get around entirely on foot. The historic Old Port is a few minutes away by car. Many of Portland’s tastiest restaurants, the Western Promenade overlooking the Fore River, and Commercial Street are within a 15-minute walk. Indulge your creative side at the Portland Museum of Art or the Maine College of Art (under a 10-minute walk). Relax at the Nine Stones Spa, then try one of the many breweries or bars as the evening approaches for a refreshing drink. For an even more scenic way to view Portland, take a ride on the Casco Bay ferry. While the building dates back to the late 1800s, the condo was thoughtfully redesigned in 2014 to give it a bright, airy, and modern feel. Throughout the space you’ll find hardwood floors, oversize windows, granite countertops, stainless steel appliances, and custom cabinetry in the kitchen and in two private bathrooms. The modern heat pump system for heating and cooling ensures you’ll always have your ideal temperature available to you. After a day spent trying some of the best restaurants in New England, come home to a polished living room with a TV providing local and national TV, a well-equipped kitchen, and such home conveniences as a stacked washer/dryer and complimentary high-speed WiFi. Each bedroom has its own TV (with local and national TV), an en suite bathroom sporting tiled showers with frameless shower doors, and remote-controlled AC, giving everyone privacy and comfort. THINGS TO KNOW Streaming services are available with guests’ own account credentials. This condo is in a multi-unit building where you will hear the occasional neighboring sounds.

’Valhalla’: Family Home on Frye Island w/ Golf!

Standish, ME, US
3 Bedrooms 7 Guests
Sep 11 - 16
$456 night

Group BBQs | Steps to Community Pool Welcome to ‘Valhalla,’ a newly built 3-bedroom, 2-bath vacation rental perfect for your Frye Island retreat! Enjoy community perks like the 9-hole golf course or spend days kayaking on Sebago Lake. After, return home to lounge on the deck and roast s'mores over the fire pit. This home offers the ideal base for your next family escape. Book your Maine island getaway today! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed - Bedroom 3: 3 twin beds - Back Living Room: 1 full sleeper sofa - Additional Sleeping: 1 portable crib COMMUNITY AMENITIES - Recreation center w/ bingo, kids activities & adult crafts - 9-hole golf course - Pickleball & tennis courts - Cafe, general store - Frye Island Provisions (food delivery service) INDOOR LIVING - 2 living areas, 2 Smart TVs - Fireplace - Dining table - Board games OUTDOOR LIVING - Furnished deck - Gas grill, picnic table - Wood-burning fire pit - Private yard KITCHEN - Refrigerator, stove/oven, dishwasher - Dishware/flatware, cooking basics, spices - Drip coffee maker, ice maker - Microwave, toaster GENERAL - Free WiFi - Central A/C & heating, ceiling fans - Linens/towels, washer/dryer - Trash bags, paper towels - Hair dryer, complimentary toiletries FAQ - Fire extinguisher in kitchen pantry - 3 exterior security cameras (facing out) - Portable crib linens not provided ACCESSIBILITY - 2-story home, 3 steps to enter - 1st-floor bedroom & full bathroom PARKING - Driveway (3 vehicles) -- THE LOCATION -- - Near biking, boating, fishing, swimming, kayaking, canoeing, bird-watching - Proximity to 12 public beaches w/ Sebago Lake access - 0.1 miles to Frye Island Swimming Pool - 0.2 miles to Frye Island Pickleball Courts - 0.8 miles to Frye Island Marina - 1 mile to Frye Island Golf Club, Frye Island Recreation Center, Frye Island Tennis Courts - 13 miles to Sebago Lake State Park (ferry required) - 31 miles to Portland International Jetport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - Your safety matters. This property features 3 exterior security cameras: 2 cameras are on the front facing the front entry area and driveway, and 1 camera is on the side facing the side yard. These cameras are outward facing and do not look into any interior spaces. They will be turned off while guests are in residence - This 2-story home requires 3 steps to enter; there is a bedroom and a full bathroom on the 1st floor - Frye Island Provisions is available for food and errand delivery services - Linens are not provided for the portable crib; it is recommended that you supply your own

Gray Woodland Escape Golf, Pool & Cinema

Gray, ME, US
5 Bedrooms 10 Guests
Aug 23 - 25
$791 night

Welcome to your tranquil retreat set on three private acres, surrounded by lush trees and natural beauty. This spacious property offers the perfect blend of relaxation and adventure for families and groups seeking to unwind and explore. Inside, enjoy a fully equipped gym to maintain your fitness routine, a cozy cinema room for movie nights, and a state-of-the-art golf simulator for some friendly competition. Take a dip in the above-ground pool or simply relax outdoors, soaking up the peaceful surroundings. When you’re ready to explore, you’ll discover plenty of outdoor activities nearby — from scenic beaches and towering mountains to charming restaurants and unique shopping destinations, all within a 30-minute drive. Whether you’re looking to unwind, stay active, or explore the stunning Maine outdoors, this property is the perfect base for your next family holiday. Book your stay today and create unforgettable memories! ★☆ NEARBY ATTRACTIONS, LANDMARKS & RESTAURANTS☆★ * Spring Meadows Golf Club - 9 min drive * Point Sebago golf course – 21 min drive * Poland Springs Golf Course – 15 min drive * Fox Ridge Gold Club – 21 min drive * Birchwood Brewing (Highly recommended) – 10 min drive * Fishermen’s Catch Restaurant and Seafood Market - 12 min drive * Deck House Tavern, \- 12 min drive * Tassel Top Park - 15 min drive * Bob’s Seafood - 17 min drive * Seacoast Adventure - 17 min drive * Kelley’s Sebago Diner - 18 min drive * Top of the Hill Grille - 19 min drive * Sebago Lake State Park Campground - 23 min drive * Naples Causeway - 24 min drive * Maine Mall, and downtown Portland – 30 min drive ★☆ KEY FEATURES ☆★ * Spacious 3-acre private lot surrounded by trees * Fully equipped gym for workouts at your convenience * Refreshing above-ground pool for summer fun (Closed from September to May) * Cinema Room: Equipped with a 100-inch TV and surround sound system. * High-tech golf simulator for year-round practice * Close to beaches, lakes, mountains, farmer’s markets, restaurants, and shopping (within 30 minutes) * Family-friendly environment with plenty of outdoor activities nearby * Quiet and peaceful location perfect for relaxation * Hot Tub ★☆ BEDROOM ARRANGEMENT☆★ BR1: 1 Queen Bed BR2: 1 Queen Bed BR3: 1 King Bed BR4: 1 King Bed BR5: 2 Full Beds ★☆ LIVING ROOM ☆★ Inside, unwind in the cozy and spacious living area, perfect for relaxing after a day of outdoor fun. The star of the show is the _dedicated cinema room_ , where your crew can enjoy movie nights on the big screen with theater- style comfort. The home also features a golf simulator for year-round entertainment and a fully equipped fitness room for guests who wish to maintain their routine. ★☆ KITCHEN & DINING ☆★ The well-equipped kitchen has everything you need to prepare meals for the whole family—from morning coffee to hearty dinners. Enjoy ample counter space, full-size appliances, and all the cookware and utensils you’ll need. ★☆ OUTDOOR SPACE ☆★ Step outside into your own private paradise. Surrounded by towering trees and peaceful natural scenery, the outdoor space is designed for both relaxation and fun. Enjoy the brand-new private pool, fully functional beginning June 1, 2026, perfect for cooling off on warm Maine summer days. A propane pool heater helps maintain a comfortable temperature, and guests are kindly asked to replace the solar pool cover after each use to help retain heat and keep the pool clean. The spacious yard offers plenty of room to unwind, play, or simply enjoy the fresh Maine air. Fire up the grill for outdoor meals, relax on the patio, or gather with family and friends after a day of exploring nearby lakes, beaches, hiking trails, and mountain adventures. ★☆ PARKING ☆★ * The driveway can accommodate 6 or more vehicles, and there is 1 additional parking spot available inside the garage. ★☆ HOUSE RULES ☆★ * No smoking * No pets allowed * No events, parties, or large gatherings * Please report any damages that occur during stay * There is a $500 fee for smoking in the premises. * Please no noise and music outside the property after 10 PM * Guests may request an early check-in (up to 3 hours before 4pm) or a late check-out (up to 2 hours after 10am), so long as there is not a reservation booked at our property for the day of your request. Please message us a day in advance to confirm availability and receive the applicable fee quote. * Extra Guests: If more guests than permitted are found at the property, we reserve the right to deny entry based on the platform’s policies. Extra guests will be treated as trespassers. An additional fee of $50/night per extra guest may apply, or we might request that you vacate the property. * If uncertain about guest numbers or daytime visitors, please reach out. We aim to prevent any misunderstandings. * Pool Rules: Please use the pool at your own risk and supervise children at all times. No diving, glass containers, or rough play in or around the pool area. For safety and cleanliness, please replace the solar pool cover after every use to help maintain the pool temperature and protect the heating system. Failure to replace the cover may result in additional maintenance charges. ★☆ Book Now & Let Us Take Care Of You! ☆★

Woods & Water | Sebago Lakefront Luxury Oasis

Casco, ME, US
5 Bedrooms 10 Guests
Aug 30 - Sep 2
$1,174 night

Woods and Water on Sebago Lake offers the perfect blend of privacy, comfort, and lakefront living. Set on 2.8 acres at the end of a quiet road, this retreat includes a 3-bedroom main house and a rustic 2-bedroom guest house. Enjoy a spacious living room, game room with shuffleboard, and a fully equipped kitchen. Outside, relax in the hot tub, gather by the fire pit, or sip coffee on the porch before heading to the lake for swimming, kayaking, or simply soaking in the peaceful surroundings. Welcome to Woods and Water, your private lakeside retreat set on 2.8 peaceful acres at the end of a quiet road. With a beautifully designed 3-bedroom main house and a rustic 2-bedroom guest house, this property blends luxury and charm while giving guests the rare gift of space, serenity, and direct access to Sebago Lake. Inside the main house, enjoy high-quality furnishings, cozy bedding, and warm, thoughtful décor. Gather in the spacious living room, cook in the fully equipped kitchen, or share meals in the dining room overlooking the woods. For entertainment, a game room with shuffleboard and a TV lounge invites hours of fun. Step outside to a true outdoor oasis: a bubbling hot tub under the stars, grill with a view, a fire pit for s’mores and stories, and a porch with plenty of seating for morning coffee or evening cocktails. Surrounded by tall pines, the property feels like its own private sanctuary while keeping you right on the water. The guest house adds even more flexibility and charm, with two bedrooms, a full bathroom, and a rustic loft featuring a huge sectional and large TV—the perfect hangout spot for kids, teens, or extra guests. Whether you spend your days kayaking, swimming, or simply relaxing on the porch while listening to the sounds of nature, Woods and Water offers the ideal balance of outdoor adventure and cozy comfort. Professionally managed by Birch Hospitality, this five-bedroom getaway ensures a seamless, memorable stay on Maine’s most beloved lake. You will have access to everything and nothing is shared. WE ARE LOCAL! - Just let us know what you need You are renting 2 homes, one across from the other.

Walk to Beach & Sebago Lake: Luxe Family Getaway!

Baldwin, ME, US
4 Bedrooms 8 Guests
Aug 31 - Sep 4
$364 night

Game Room | Al Fresco Dining | BBQ Ready | Paddleboards Seeking easy access to Sebago Lake with all the comforts of home? Book this 4-bed, 3-bath vacation rental! The newly built townhome has an open-concept living area, a fully stocked kitchen, and outdoor spaces fit for the whole crew. Fish and swim at the neighborhood beach, or explore the hiking trails throughout Sebago Lake State Park! Back home, get competitive with a game of pool, then unwind with a drink on the deck. It's up to you! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 2 twin beds - Bedroom 3: 2 twin beds - Bedroom 4: 1 king bed OUTDOOR LIVING - Screened deck - Dining area, gas grill, fire pit - Covered patio - 1 convertible paddleboard/kayak, 1 paddleboard - Community beach & lake access INDOOR LIVING - 2 Smart TVs w/ cable - Dining table, breakfast bar - Game room, pool table, card table - Board games KITCHEN - Refrigerator, stove, oven w/ air fryer setting, dishwasher - Dishware/flatware, cooking basics, spices - Drip coffee maker, blender - Microwave, toaster GENERAL - Free WiFi - Keyless entry - Central heating, portable A/C units (free-standing), ceiling fans - Linens/towels, iron/board - Washer/dryer (detergent provided) - Trash bags, paper towels ACCESSIBILITY - 2-story townhome w/ walk-out basement, 2 steps to enter - 1st-floor bedrooms & full bathroom PARKING - Driveway (6 vehicles) - Boat/trailer parking available ADDT’L ACCOMMODATIONS - An additional property is available on-site w/ a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- - Walk to Sebago Town Beach, Sebago Lake Marina & Sebago Boat Ramp - 1 mile to Long Beach: bar, restaurant, grocery store - 10 miles to Sebago Lake State Park & Naples Causeway - 25 miles to Portland International Jetport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story townhome with a basement requires 2 steps to enter the front door; there are 2 bedrooms and a full bathroom on the 1st floor

Waterfront home with a fireplace, grill, deck, washer/dryer, & AC - dog-friendly

Raymond, ME, US
3 Bedrooms 6 Guests
Aug 17 - 19
$401 night

Escape to the Maine countryside and unwind at Panther Run River Retreat. Located directly across the street from the Historic Maine Fish Hatchery, this area is known for making Raymond the "Home of Landlocked Salmon." During your stay, tour the hatchery, enjoy peaceful walks through Hacker’s Hill Preserve, or tee off at the nearby Val Halla Golf & Recreation Course. Back at the property, relax and take in the tranquil river views from your private outdoor space. Fire up the gas grill for a summer barbecue, gather around the propane fire pit in the evening, or enjoy a meal at the picnic table overlooking the water. Just a short walk or drive away, you’ll also find public pickleball, tennis, and basketball courts, offering even more opportunities for outdoor recreation. Inside, the sun-filled living room provides a cozy place to relax while streaming your favorite shows and movies. The fully furnished sunroom offers another inviting space to unwind with your morning coffee or a good book. The well-equipped kitchen features beautiful cherry wood cabinetry, stainless steel appliances, and a breakfast bar, making meal preparation a breeze. Enjoy casual meals at the breakfast bar or gather around the formal dining table for memorable family dinners. The spacious, tastefully decorated bedrooms provide a comfortable retreat after a day of exploring, while additional conveniences include partial air conditioning and a private washer and dryer. As evening falls, settle in around the fire pit, listen to the peaceful sounds of the river, and enjoy Maine’s spectacular star-filled skies—the perfect ending to another unforgettable day. THINGS TO KNOW Guests may use the dock for personal kayaks from Memorial day until the end of September. Streaming services available with guests’ own account(s). Active cameras outside on the driveway and doorbell

Modern Gem on 15 Acres, 5 Mi to Old Orchard Beach!

Saco, ME, US
3 Bedrooms 6 Guests
Aug 28 - Sep 1
$364 night

Newly Renovated | EV Charger | Pets Welcome w/ Fee | Chef's Kitchen Experience Maine’s coast in style at 'The Luna Lodge!' Boasting a spacious interior with luxury features, this 3-bedroom, 2-bath Saco vacation rental offers an effortless escape for families or friend groups. Want to venture out? Take the kids to Funtown Splashtown USA, enjoy shoreline strolls and lobster rolls in Old Orchard Beach, or visit Portland. Later, walk the acreage with your pets and gather for a cozy movie night. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 queen bed - Bedroom 3: 1 twin daybed w/ 1 twin trundle - Additional Sleeping: 1 portable crib INDOOR LIVING - Open-concept layout - Flat-screen TVs w/ cable, complimentary streaming services - Rainfall shower heads, LED lighted mirrors - Dry bar w/ beverage cooler - Mudroom w/ shoe storage & coat hooks - Built-in bar seating - Movies, board games, books, Nintendo console - Gas fireplace - Pet bed, food & water bowls OUTDOOR LIVING - Spacious yard, wooded views - Private balcony w/ lounge chairs - Fire pit, Adirondack chairs - Beach towels KITCHEN - High-end appliances, under-cabinet lighting - Samsung Bespoke refrigerator, stove/oven, dishwasher - Coffee bar w/ dual drip/single-serve coffee maker, starter coffee & pods - Blender, Crockpot, toaster, microwave - Cooking basics, spices, dishware & flatware - Ice maker, trash bags/paper towels - Dining nook w/ table & bench seating - High chair GENERAL - Central heating & A/C - Washer/dryer, laundry detergent, iron/board - Linens/towels, complimentary toiletries, hair dryer - Free WiFi - Keyless entry FAQ - 4 exterior security cameras (facing out) - Pet fee (paid pre-trip) ACCESSIBILITY - 2-story home, 1 exterior step to enter - 1 full bathroom on 1st floor - All bedrooms on 2nd floor PARKING - Driveway (4 vehicles) - RV/trailer parking allowed on-site (36' spot) - High-speed EV charger available -- THE LOCATION -- - Tranquil setting near nature preserves, golf courses & I-95 - 2 miles to Aquaboggan Water Park & 4 miles to Funtown Splashtown USA - 5 miles to Old Orchard Beach, Palace Playland & fishing pier - 5 miles to downtown Saco & 6 miles to Biddeford - Within 15 miles of Portland hotspots: Old Port, West End, Portland Head Light, Bug Light Park, museums, breweries, shops, restaurants - 11 miles to Portland Int'l Jetport (PWM) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking or vaping - Pet friendly w/ $125 fee (+ fees & taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story home requires 1 exterior step to enter. While it offers 1 full bathroom on the 1st floor, all bedrooms are located on the 2nd floor and require interior stairs to access - Your safety matters. This property features 4 exterior security cameras: cameras 1-3 are Ring doorbell cameras located at each entrance facing out, and camera 4 is located in the parking area facing the driveway. The cameras do not look into any interior spaces. The cameras record video and sound when activated by motion

A Shore Thing by Bayley Vacation Rentals

Scarborough, ME, US
4 Bedrooms 9 Guests
Aug 30 - Sep 2
$892 night

Be the first guest & discover our brand-new coastal retreat, perfect for your next getaway! Enjoy modern amenities, a fully equipped kitchen, and a cozy living area that’s perfect for relaxing after a day of exploring. A Shore Thing offers the perfect balance of comfort and convenience. Book now and be one of the first to experience this fresh new vacation home! KITCHEN - Range Cooktop - Stove - Microwave - Keurig - Phillips Barista - Dishwasher - Dining table for 8 - Plates, bowls, glasses, silverware, pots, pans - Kitchen Towels - Sponge - Starter dish soap - 2 rolls of paper towels BATHROOM #1 - First Floor - No shower/tub - Toilet - Sink - 2 rolls of toilet paper - Hand towels - Hand soap BATHROOM #2 - Second Floor -Shower/Tub combo - Toilet - Sink - 2 rolls of toilet paper - Hand towels - Hand soap BATHROOM #3 - Second Floor - En-suite - Standing shower - Toilet - Sink - 2 rolls of toilet paper - Hand towels - Hand soap BEDROOM #1 - First Floor - Queen - 2 Pillows - Sheets, comforter - 4 body towels - Closet - NO Dresser - NO TV BEDROOM #2 - Second Floor - Queen - 2 Pillows - Sheets, comforter - 4 body towels - Dresser - Closet - NO TV BEDROOM #3 - Second Floor - 1 Twin - 1 Full - 1 Pillow on twin bed - 2 Pillows on Full bed - Sheets, comforter - 2 body towels for twin bed - 4 body towels for full bed - Closet - Dresser - TV BEDROOM #4- PRIMARY - Second Floor - Queen - 2 Pillows - Sheets, comforter - 4 body towels - Closet - Dresser - TV - En Suite bathroom EXTRA - Ornamental Fireplace in living room - Outdoor Cameras - Washer/ Dryer in house (starter laundry detergent provided) - Propane Grill - Outdoor Furniture - Central Air throughout house - NO Firepit - Dogs are the only permitted pet (2 dog max) - NO Smoking - SEASIDE SCOOP *Garage access isn’t available BEACH - 0.1-mile to the beach, 3-minute walk - A long sandy, wide open beach that is 4 miles long starts at the jetty of Pine Point and goes until it meets Old Orchard Beach - Beach gear not provided PARKING - 4 spots in the driveway - This property allows a maximum number of vehicles for each reservation, as seen above. Any additional or unregistered vehicles may be subject to towing at the owner’s expense. Please plan accordingly and reach out if you have any questions about parking during your stay. HOUSE INFORMATION - Built in 1900 - Remodeled 2024 Bars | Restaurants | Beach • Beach - 0.1 miles | 3 Minute Walk • The Bait Shed • Bayley’s Lobster Pound • Salty Bay • Garage BBQ • Dog Days Gift Shop • The Clambake • Pine Point Grill • Trolley that runs from Pine Point to OOB This property has contactless check-in! All information can be found in your reservation guidebook after booking. Door codes are released on check-in day.

Vacation Rentals in Windham by Amenities & Features

Get to Know Windham

Windham, Maine, is a picturesque town that offers a serene escape into the heart of New England charm. Located in the Lakes Region of Southern Maine, Windham serves as a gateway to a natural playground, making it an ideal destination for outdoor enthusiasts and those seeking a peaceful retreat. The town is nestled on the shores of Sebago Lake, Maine's second-largest lake, which is renowned for its crystal-clear waters and excellent conditions for boating, fishing, and swimming. The lake is a haven for anglers looking to catch landlocked salmon and trout, while its vast expanse is perfect for sailing and waterskiing. Sebago Lake State Park provides ample opportunities for camping, picnicking, and hiking, with trails that meander through lush forests and along the scenic lakefront. Windham's proximity to Portland, just a short drive away, allows visitors to enjoy the tranquility of a small town while having easy access to the amenities and attractions of a larger city. The town itself, however, has its own set of charms, including local shops, cozy restaurants, and community events that showcase the warmth and hospitality of its residents. For history buffs, the Windham Historical Society offers a glimpse into the town's past, with a collection of artifacts and exhibits that tell the story of the area's development. The society often hosts events and lectures that delve into various aspects of local and regional history. In the fall, Windham transforms into a quintessential New England landscape, with vibrant foliage that paints the countryside in shades of red, orange, and gold. This season is particularly magical for scenic drives, photography, and enjoying the crisp autumn air. During the winter months, the region becomes a snowy wonderland, with cross-country skiing and snowshoeing trails available for those who love winter sports. The nearby Shawnee Peak and Sunday River ski resorts also offer downhill skiing and snowboarding for all skill levels. Windham's community spirit shines through its local festivals and fairs, which often feature live music, crafts, and traditional Maine foods. The town's commitment to preserving its natural beauty and fostering a welcoming environment makes it a delightful destination year-round. Whether you're seeking outdoor adventure, a taste of small-town life, or simply a place to unwind amidst beautiful surroundings, Windham, Maine, is a destination that offers a little something for everyone.
Windham, Maine, nestled in the picturesque New England region, experiences a four-season climate that offers a diverse range of weather conditions throughout the year, each with its own unique appeal. Winter, from December to February, is cold and snowy, with average temperatures ranging from 10°F to 31°F. Snowfall is significant, making Windham a winter wonderland, ideal for snow sports and cozy evenings by the fire. January is typically the coldest month, so visitors should come prepared with warm clothing and snow gear. Spring, from March to May, brings a gradual warming trend with temperatures ranging from 24°F to 65°F. This season can be unpredictable, with late snowfalls or early heatwaves. The melting snow and spring rains contribute to the lush greenery that emerges, making it a beautiful time for nature walks as the landscape reawakens. Summer, from June to August, is the warmest and most popular time to visit. Average temperatures range from 54°F to 80°F, with July being the hottest month. The humidity can be high, but it's also the season when Windham's lakes and outdoor activities are most enjoyable. Occasional thunderstorms are common, so it's wise to have a flexible itinerary. Autumn, from September to November, is a spectacular season in Windham, with the foliage turning vibrant shades of red, orange, and yellow. Temperatures cool down to a range of 36°F to 70°F, and the humidity drops, making it a perfect time for hiking and enjoying the fall scenery. This is also a popular season for visitors who come to witness the famous New England fall foliage. The most pleasant weather conditions are often found in late spring, when the temperatures are moderate and the landscape is blooming, and in early fall, when the humidity is lower and the autumn colors are at their peak. These times offer a balance of comfortable weather and the opportunity to experience Windham's natural beauty without the peak summer crowds. Regardless of the season, Windham's climate is part of its New England charm, offering visitors a chance to experience the quintessential seasonal changes that make this region so beloved. Whether you're looking to enjoy winter sports, summer lakes, spring blooms, or fall foliage, Windham provides a picturesque backdrop for a memorable visit.
Windham, Maine, may not be the first destination that comes to mind for a cultural enthusiast, but this charming town offers a tranquil setting for those looking to explore the arts, history, and local customs of New England. While Windham is a smaller community, it is within close proximity to Portland, Maine's cultural hub, which is just a short drive away. However, Windham itself has its own unique offerings. The Windham Historical Society provides a glimpse into the area's past, with a collection of artifacts and exhibits that tell the story of the town's development from its early days to the present. For art lovers, the Sebago Lake region, of which Windham is a part, hosts local artists and craftsmen whose works reflect the natural beauty of Maine. Galleries in the area showcase paintings, sculptures, and crafts that are inspired by the state's landscapes and seasons. The nearby town of Gorham often has art events and exhibitions at the University of Southern Maine Art Gallery, which features contemporary works by regional artists. Live music can be found at local venues and seasonal festivals. The Windham Summerfest is an annual event that celebrates the community with music, food, and entertainment. Additionally, the nearby city of Portland offers a rich music scene with venues like the State Theatre and Port City Music Hall, where a variety of live performances can be enjoyed. For a more immersive experience in local customs, Windham's proximity to Portland allows for easy access to the city's First Friday Art Walk, where galleries and museums open their doors to the public for free. This monthly event is a fantastic way to engage with the local art community and experience the vibrant culture of the area. Windham's natural setting also provides a serene backdrop for those who appreciate the arts. The town is nestled among rolling hills and pristine lakes, offering inspiring vistas for plein air painting or photography. The local landscape is a canvas in itself, changing with the seasons and providing endless opportunities for artistic exploration. While Windham is a quieter destination, its New England charm and access to the cultural activities of the greater Portland area make it a delightful spot for those who enjoy the arts, history, and local customs. It's a place where one can enjoy the peacefulness of a small town while still being within reach of a lively cultural scene.
Windham, Maine, nestled in the scenic beauty of New England, offers a delightful array of activities that are sure to captivate children and provide a memorable family experience. Start your adventure at Seacoast Adventure, a fun park that offers a variety of attractions suitable for all ages. During the summer, kids can enjoy go-karts, mini-golf, and a sky swing, while winter brings the excitement of snow tubing. The park's Deck House Tavern provides a family-friendly dining option with a menu that caters to both adults and children. For those who love the great outdoors, Windham is a gateway to the Sebago Lake region. Spend a day at Sebago Lake State Park, where kids can splash in the water, build sandcastles on the beach, or explore the park's hiking trails. The clear, clean waters of the lake are perfect for a family swim or a leisurely boat ride. The Windham Historical Society offers a glimpse into the past with its Village Green, where families can explore historic buildings and learn about the area's heritage. Although it may be more appealing to older children with an interest in history, the picturesque setting makes it a pleasant stop for a family picnic. For a unique cinematic experience, take the family to the Pride's Corner Drive-In. This nostalgic outdoor movie theater allows you to watch the latest films under the stars, a special treat that combines entertainment with the charm of yesteryear. If your children are animal lovers, a visit to the Maine Wildlife Park in nearby Gray is a must. Here, they can see moose, bears, lynx, and other animals native to Maine. The park's interactive displays and educational programs make it both a fun and informative outing. For a more relaxed day, visit Tassel Top Park on the shores of Sebago Lake. With its sandy beach, snack shack, and nature trails, it's an ideal spot for families to unwind and enjoy Maine's natural beauty. Windham also offers a variety of dining options that are sure to please even the pickiest of eaters, from classic American fare to delicious ice cream at local parlors. In Windham, Maine, families can enjoy a blend of outdoor adventure, educational experiences, and simple pleasures, all set against the backdrop of New England's timeless charm. Whether you're seeking thrills at an adventure park or a peaceful day by the lake, Windham has something to offer for every child and those young at heart.
Windham, Maine, nestled in the scenic beauty of New England, is a treasure trove of natural wonders and outdoor activities for those who seek to immerse themselves in nature. This charming town, located near the Sebago Lake region, offers a serene escape with its lush landscapes, waterways, and trails. Sebago Lake, Maine's second-largest lake, is a centerpiece of outdoor recreation in the area. It provides a perfect setting for boating, fishing, and swimming in its crystal-clear waters. The lake is known for its landlocked salmon and trout, making it a popular destination for anglers. Around the lake, visitors can find numerous spots for picnicking and enjoying the panoramic views. For hiking enthusiasts, the Mountain Division Trail offers a multi-use path that meanders through the picturesque Maine countryside. This trail is ideal for walking, biking, and even horseback riding, allowing visitors to take in the natural beauty at their own pace. The nearby Presumpscot River Preserve is another natural gem where outdoor lovers can connect with the environment. The preserve features trails that run alongside the river, providing opportunities for wildlife observation, photography, and the simple pleasure of a peaceful walk through the woods. Birdwatchers will find the Donnabeth Lippman Park a haven for local and migratory birds. The park's wetlands and forested areas are home to a variety of bird species, offering a tranquil spot for observation and listening to the melodic bird songs. For a more adventurous experience, the Windham area offers kayaking and canoeing opportunities on its many rivers and streams. Paddling through these waterways, one can discover secluded spots and enjoy the serenity of the Maine wilderness. In the winter months, Windham transforms into a snowy wonderland, with cross-country skiing and snowshoeing becoming popular activities. The landscape blanketed in white offers a different kind of beauty, and the crisp air invigorates the soul. Lastly, the nearby White Mountains of New Hampshire are just a short drive away, offering even more outdoor pursuits such as hiking, climbing, and skiing. The proximity to these majestic peaks adds another layer of allure for those staying in Windham. Windham, Maine, with its natural splendor and array of outdoor activities, is a destination that truly resonates with those who yearn to connect with nature. Whether it's on the water, in the forest, or amidst the mountains, Windham provides an idyllic backdrop for nature lovers to explore and enjoy.
Windham, Maine, is a charming town nestled in the scenic Lakes Region of the state, offering a peaceful retreat with easy access to outdoor activities and local attractions. While it may not have the extensive transportation infrastructure of a major city, there are still several options for travelers to arrive, depart, and explore the area. Most visitors traveling to Windham will likely fly into the Portland International Jetport, which is approximately a 30-minute drive away. From the airport, renting a car is the most convenient option for reaching Windham and provides the flexibility to explore the surrounding region at your own pace. Ride-sharing services like Uber and Lyft, as well as local taxi companies, are also available for the journey from the airport to Windham. For those who prefer to travel by bus, there are regional bus services that connect Portland to Windham, although the schedules may be less frequent than in larger urban areas. Once in Windham, having a car is advantageous as public transportation options within the town are limited. Windham itself is not particularly walkable for a typical visitor, especially if you plan to visit various points of interest or enjoy the natural beauty of the area. The town is spread out, and many of the attractions, such as Sebago Lake, local parks, and hiking trails, are best accessed by car. However, the town center does have a selection of shops and restaurants that can be enjoyed on foot if you choose accommodations nearby. For those looking to explore the great outdoors, Windham offers easy access to the Sebago Lake region, where boating, fishing, and swimming are popular activities during the warmer months. In the winter, the nearby Shawnee Peak and other ski resorts provide opportunities for skiing and snowboarding. In summary, while Windham may not have the extensive public transportation systems of larger cities, it is well-serviced by road and is a short drive from Portland's airport. Renting a car is the most practical way to enjoy the freedom to explore Windham and the surrounding natural attractions at your leisure.

Windham FAQs

Windham offers a variety of activities for visitors. You can explore the Sebago Lake region, which is perfect for boating, fishing, and swimming. Enjoy hiking and wildlife watching at the Donnabeth Lippman Park, or play a round of golf at one of the local courses. In the winter, snowmobiling and cross-country skiing are popular. The Windham Historical Society provides a glimpse into the area's past, and for shopping enthusiasts, the Windham Mall and local boutiques offer a range of shopping options.
Windham boasts a variety of dining options ranging from casual to fine dining. Some local favorites include the Sebago Lake Lodge & Cottages for waterfront views, Masa's Sub & Grill Pizzeria for Italian fare, and Buxton Common for American cuisine. For a unique experience, try the Chute's Family Restaurant, known for its home-style cooking.
Yes, Windham offers a range of accommodations. Visitors can choose from lakeside cottages, cozy bed and breakfasts, and traditional hotels. The Sebago Lake Lodge & Cottages and Microtel Inn & Suites by Wyndham are popular choices for their comfort and proximity to local attractions.
The best time to visit Windham depends on the activities you're interested in. Summer is ideal for lake activities and enjoying the outdoors. Fall brings stunning foliage and is perfect for hiking and scenic drives. Winter is great for snow sports, while spring offers the chance to see the landscape come to life. Each season has its charm, so consider what you want to experience when planning your trip.
Absolutely! Families can enjoy a day at Sebago Lake, where there are beaches and picnic areas. The Windham Skate Park is a hit with kids, and the Seacoast Adventure offers go-karts, mini-golf, and a ropes course. During the winter, families can go sledding or ice skating at local parks.
The most convenient way to get around Windham is by car. You can rent a vehicle from nearby Portland if you're flying in. There is limited public transportation within Windham, so having a car will give you the flexibility to explore the surrounding areas and attractions at your own pace.

More space, more privacy, more points with every home rental.

What makes Homes & Villas by Marriott Bonvoy a unique home rental experience? Unlike other home rental sites like AirBNB, when you book a vacation rental with Homes & Villas by Marriott Bonvoy you always have the whole place to yourself. Plus, as a member of Marriott Bonvoy, you can earn points towards free nights with every stay.

Vacation Rentals Near Windham

Saved Home Image
Sign in or join now to view and save the homes you love