Large group vacation rentals in Waldoboro, ME

Explore 183 large group vacation rentals, homes, and villas in Waldoboro, ME for your next getaway or business trip. With space for everyone, enjoy the comfort and privacy of a home designed for gathering, alongside premium amenities such as Air Condition Homes and Best Affordable Homes. Throughout your stay, spend time together, share meals, and relax in spacious living areas that make group travel feel cohesive. With options starting as low as $131 per night and homes offering up to 7 bedrooms and 5 bathrooms, it's easy to book a stay that fits your group. And with 24/7 local support and high-speed Wi-Fi, everyone stays connected and protected. Marriott Bonvoy members enjoy the added benefit of earning points on every stay, making each trip more rewarding than the last. Book your next group getaway with Homes & Villas by Marriott.

183 Great for Groups in Waldoboro

The Eagle’s Nest

Waldoboro, ME, US
2 Bedrooms 4 Guests
Aug 24 - 29
$777 night

Wake up to panoramic views of the Medomak River at this two-bedroom plus loft Waldoboro retreat—a private waterfront haven with a beautifully remodeled interior, wrap-around deck, and direct access to the river, Muscongus Bay, and the open Atlantic. Enjoy spectacular sunrises and serene moonlit nights from this idyllic perch. Set amid 11 acres of wildflower meadows and fireflies, this two-level home rests on the western banks of the Medomak River, just five miles south of downtown Waldoboro. You’ll be a short paddle from where the river meets Muscongus Bay, and only 21 miles from the art galleries, restaurants, and scenic breakwater of Rockland. Keep an eye out for bald eagles, ospreys, seals, and other coastal wildlife. A long private driveway leads to ample parking and a peaceful waterfront setting. Inside, the open living space has been fully remodeled with hardwood floors, vaulted ceilings, and a wall of windows framing the water. After a day of kayaking, unwind on the comfortable sofa, play cards around the glass coffee table, or stream a movie on the large flatscreen TV. The home offers WiFi, a washer/dryer, and inviting spaces to relax. The fully renovated kitchen features stainless steel appliances, generous counter space, and all the essentials for preparing Maine-inspired meals. Gather at the breakfast bar or six-person dining table, and when the weather’s warm, step outside to grill and dine on the deck while soaking up the stunning views. Outdoors, spend your days kayaking or canoeing, basking in the sun on the wrap-around deck, or exploring more than 400 feet of private tidal waterfront with Maine’s classic granite rocks and tide pools. Inside, a second sitting room offers the perfect nook for reading or enjoying the coastal breeze through open glass doors. The home accommodates up to six guests with two bedrooms, a loft, and two-and-a-half bathrooms. The open loft-style primary bedroom overlooks the river and great room below, offering a king bed and private bath. On the main floor, you’ll find one bedroom with a queen bed and another with twin bunk beds—ideal for families or friends traveling together. Located along scenic Route 1, this property places you in the heart of Midcoast Maine’s natural beauty. Visit nearby Waldoboro’s Main Street for local shops and dining, or follow the river south to the historic Pemaquid Point Lighthouse. Explore downtown Rockland for seaside charm and top-tier dining, including the award-winning restaurant Primo. Camden Hills State Park—known for its panoramic ocean views and vibrant autumn colors—is just 26 miles away. Boothbay Harbor, the Coastal Maine Botanical Gardens, and even Acadia National Park are within reach for memorable day trips. Your peaceful Midcoast Maine escape awaits at this beautifully appointed Waldoboro waterfront home—where each sunrise, tide, and breeze reminds you why this place is unforgettable.

Near Lakes, Bay & Trails! Historic Waldoboro Gem

Waldoboro, ME, US
3 Bedrooms 6 Guests
Aug 24 - 26
$181 night

Experience the best of Mid-Coast Maine at this historic Waldoboro vacation rental. Built by Conrad Heyer — one of the earliest-born people ever photographed — this 3-bedroom home offers a deep connection to American history. Spend your summer days paddling the Medomak River, launching your boat into the bay just 3 miles away, or exploring neatby Rockport. After a day of coastal adventure, return to your private deck to relax under the stars. Book your escape today! -- THE PROPERTY -- In-Unit Laundry | Fast Free WiFi | 1,200 Sq Ft | Bedroom Suite on First Floor Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Additional Sleeping: 1 Portable Crib OUTDOOR LIVING: Deck w/ picnic table, fire pit (bring your own wood), private yard, 5-burner charcoal grill INDOOR LIVING: Smart TV w/ cable, 6-person expandable dining table, renovated interior, DVD/movie selection, games, books KITCHEN: Fully equipped w/ cooking basics, dishwasher, tile countertops, microwave, drip coffee maker w/ coffee, hot chocolate, tea, sugar/sugar-free sweetener, & creamer (all non-organic), toaster, knife set, Crockpot GENERAL: Complimentary toiletries, towels/linens, trash bags/paper towels, broadband wireless internet to support multiple devices, 1st floor bed & bath, A/C window units, ceiling fans, tower fans, baby/toddler bath accessory FAQ: Exterior security cameras (facing out) ACCESSIBILITY: 2-story, 3 steps to enter, bedroom & bathroom on 1st floor (2 steps to enter bedroom) PARKING: Driveway (3 vehicles) -- THE LOCATION -- EXPLORE MAINE: Rockland (20 miles), Belfast (35 miles), Brunswick (40 miles), Bangor (68 miles) ON LAND: Moody’s Diner (3 miles), Waldoboro Recreation Complex (5 miles), Waldoboro Town Forest (5 miles), Beth's Farm Market (6 miles), Davis Stream Preserve (7 miles), West Branch Preserve (10 miles), The Camden Snow Bowl (21 miles), Lost Valley Ski Area (66 miles), Acadia National Park (87 miles) ON THE WATER: Waldoboro Public Landing (4 miles), Damariscotta Lake State Park (7 miles), Medomak River (12 miles), Morgans Mills (12 miles), Lucia Beach (22 miles) WINE & ART: Sweetgrass Farm Winery and Distillery (9 miles), Savage Oakes Vineyard and Winery (10 miles), Oyster River Winegrowers (12 miles), Tidemark Gallery (12 miles), Landing Gallery (19 miles), Breakwater Vineyards (20 miles), Cellardoor Winery (26 miles) AIRPORTS: Augusta State Airport (28 miles), Portland International Jetport (69 miles), Bangor International Airport (72 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 2-story property requires 2 steps to enter. It offers a bedroom and bathroom on the 1st floor (the bedroom requires 2 steps to enter) - NOTE: Your safety matters. This property features exterior security cameras facing the entry door, parking area, front of the house/road, backyard, and both side yards. The cameras are outward facing and do not look into interior spaces. The cameras do not actively record video or sound while guests are in residence - NOTE: Guests will need to bring their own firewood for the fire pit. Wood can be purchased locally and is typically between $5-$10 per bundle

Sea Heather Cottage

Waldoboro, ME, US
2 Bedrooms 4 Guests
Sep 25 - 27
$446 night

Escape to Sea Heather Cottage, a peaceful seaside retreat on a private peninsula in Waldoboro, Maine. Surrounded by water views in almost every room, this two-bedroom cottage blends coastal charm with complete tranquility. Perfect for couples seeking a romantic escape or families looking to unwind; guests can kayak, swim, stroll the walking trail, or simply relax on the deck as the tides roll in. Just 20 minutes to Damariscotta and 35 minutes to Rockland, you’ll enjoy both seclusion and easy access to Midcoast Maine’s shops, restaurants, and attractions. What you will love: - Water Views Everywhere: almost every room frames the tidal beauty of the cove. - Queen Bedroom Retreat: A sunlit bedroom with direct deck access, large windows, and calming water views. - Full Bedroom: A quiet room with a full bed with panoramic views of the peninsula & field, perfect for a couple or additional guests. - Coastal Charm: Original pine floors, cozy furnishings, and thoughtful décor create a warm and welcoming atmosphere. Outdoor Living - Step outside and immerse yourself in the ever-changing coastal scenery: - Launch kayaks or paddleboards (bring your own or rent nearby) and explore from the shore. - Swim, watch for playful seals, and enjoy the calls of seabirds. - Wander the walking trail around the property for peaceful pauses in nature. - Relax in Adirondack chairs with your morning coffee or evening wine, taking in sweeping views of the water and sky. Though secluded, Sea Heather is only a short drive from Midcoast Maine’s vibrant towns: - 20 minutes to Damariscotta for shopping, galleries, and dining. - 35 minutes to Rockland, home to festivals, museums, and fresh seafood. - Easy day trips to lighthouses, coastal trails, and charming villages. Here, the tides set the rhythm of your days, the views change with every hour, and the quiet beauty of the sea invites you to truly unwind. Dogs are considered, please contact us prior to booking with the age and breed of dog(s) for approval.

Loon Cove

Nobleboro, ME, US
3 Bedrooms 6 Guests
Sep 5 - 8
$576 night

Your own remote Maine retreat awaits! Your secluded lakefront paradise sports a contemporary design mixed with an old Maine cabin, giving it a welcoming atmosphere. Floor-to-ceiling windows adorn the living room which has been completely renovated as of 2022 with new furniture. Unwind on comfortable furnishings here and watch the sun glistening on the lake, and witness beautiful sunsets for days. The open space of the gourmet kitchen has top-of-the-line cookware, tableware, and a chef’s stove, ready to prepare everything from a tasty snack to a full-blown feast. All bedrooms have been renovated with new furniture as well creating a comfortable and pristine space for downtime. For a second guest couple or grandparents of a family, there is a newly painted and decorated detached suite above the garage with skylights and stunning lake views. The 150’ lakefront features a gently sloping pebbled area that’s great for little ones to play in the water, a new dock with a ladder that can accommodate an 18’ boat, and another spot that’s perfect for launching one of the kayaks, paddleboard, or Sunfish that are all available to guests. Gaze at the lake or the giant pines from the hammock, or close your eyes and drift off for a nap to the sound of the water lapping at the shore. Located on a private road with only four other houses in the immediate area, you’ll have much of the lake to yourself. Watch the loons swimming just off the shore or enjoy the sunset directly across the lake from the privacy of your home, completely removed from the outside world. You’ll also be close to amazing attractions should you get out. The outstanding Ginger Mousse Bakery is just an easy walk or three-minute drive up the road, and fine dining and shopping are 15 minutes down Route 1 in Damariscotta. Here, you can check out an art museum or two. World famous waterfront seafood at Muscongus Bay Lobster and Shaw’s Wharf are just 20 minutes. Climbing Mt. Megunticook or taking the boat out to Monhegan. Nearby activities also include golf, as well as local trails. Whatever you choose, there is no shortage of adventures near this lovely home! THINGS TO KNOW Streaming services are available, but guests must log in with their accounts.

Loon’s Cry on South Pond

Warren, ME, US
4 Bedrooms 8 Guests
Aug 26 - 28
$733 night

A gorgeous setting awaits at this secluded, lakefront home on the shores of South Pond. This is a perfect place for long, relaxing days spent swimming, kayaking, bass fishing, and boating from the private dock at the water’s edge. This quiet, waterfront home sits at the end of a mile-long country road in Warren with South Pond (548 acres) outside the back door. It’s a serene location that’s close to some of the most beloved towns and scenery of Mid-coast Maine, with Camden, Rockport, and Rockland within a 13-mile drive. Bring your own watercraft at the local boat launch (one mile), attend the lively Maine Lobster Festival (nine miles), take a day trip out to Monhegan Island from Port Clyde (19 miles), or hike one of Mid-coast Maine’s hundreds of public trails. Thanks to the wonderful afternoon sunshine that the property receives, you’ll delight in lounging on the deck and taking in the lakefront view. Light the gas grill each evening for a barbecue dinner and count the stars in the night sky from a seat by the outdoor firepit while listening to the loon’s cry. There’s plenty of wildlife in the area, including rabbits, raccoons, deer, owls, ducks, and even a pair of bald eagles that call South Pond their home. Step inside and find a space that’s warm, comfortable, and familiar with generous windows framing the lake out back. Store your groceries in the updated kitchen cabinets, gather around the farm table for meals and family board games in the evenings, enjoy the walkout basement game room with TV and comfy lounging, or curl up with a good book in the study. There are two queen-sized bedrooms upstairs with a full, recently updated bathroom and a full-sized bedroom and study with a pull-out twin-sized bed downstairs. The downstairs also has a full, recently renovated bathroom with a tub and shower for those who prefer soaking after a challenging day hike up Mount Battie. Additional home conveniences include a private washer/dryer, complimentary Wi-Fi, and mini-splits for heating and air conditioning. THINGS TO KNOW Pets are allowed for an additional cleaning fee. There is ample parking available: 2 slots in front of the house with an additional parking area slightly further away. The house sits close to a railroad track and occasionally (once or twice a week), the train will come through during the day and toot its horn. The conductors will even wave back if they see you waving. Bald eagles nest on the property. They are protected. Any attempt to interfere with the bird or its nest is strictly prohibited. Please help us protect them by being aware and careful.

La Vita Semplice

Waldoboro, ME, US
1 Bedrooms 2 Guests
Sep 10 - 12
$478 night

La Vita Semplice offers a coastal escape in Waldoboro, placing you within Maine’s scenic Midcoast corridor and close to the water, where ocean views and a relaxed rural setting set the tone for your stay. This inviting 1-bedroom, 1-bath unit spans 1,400 square feet and comfortably accommodates up to 4 guests, making it a wonderful choice for couples, small families, or a quiet getaway with friends. Inside, the home feels warm, bright, and thoughtfully appointed, with a private living room and a comfortable sleeping setup that includes a queen bedroom plus a sleep sofa in the living area. Guests frequently mention how comfortable and well maintained the home feels, along with the added convenience of the extra sleeping space. The layout is simple and practical, creating an easy place to unwind after a day exploring the coast. The full kitchen comes ready for casual meals and longer stays, featuring everything you’d need to make a wonderful meal in home to enjoy. Whether you’re preparing breakfast before heading out or grilling dinner after a day of sightseeing, everything you need is close at hand. Amenities like washer and dryer, central heating, air conditioning, linens, towels, shampoo, hair dryer, and essentials help make your stay seamless and comfortable. Step outside to enjoy the decked area, garden, outdoor seating, and BBQ grill. With ocean-view surroundings and beach essentials available, the outdoor spaces invite slow mornings and easy evenings. Guests also appreciate the convenience of private entrance, self check-in, and fast Wi‑Fi with laptop-friendly a, making the property equally suited for vacation relaxation or remote work. For downtime, you’ll find TV, books, and reading materials for a cozy night in or escaping from the rain. From this Midcoast location, guests can enjoy scenic drives, coastal villages, marinas, museums, boating, fishing, hiking, whale watching, antiquing, and wildlife viewing nearby. La Vita Semplice offers a peaceful, comfortable base with a beautiful setting and thoughtful amenities—book your stay and enjoy a truly simple coastal retreat. THINGS TO KNOW Streaming TV services require guest accounts to access.

Little Loon Farm

Warren, ME, US
3 Bedrooms 6 Guests
Oct 31 - Nov 2
$651 night

Little Loon Farm is a quiet, historic Georgian farmhouse located in the middle of Mid-Coast Maine. Built in 1820, every room in the 2000 square-foot house is bright and airy, oozing charm and character; from its original pumpkin pine floors to the thoughtful updates to accommodate modern needs. The house is close to the coast and a short drive to everything mid-coast Maine has to offer. There are beaches, mountains, lighthouses, fishing, lakes, golf, hiking, ATV trails, kayaking, festivals, and an abundance of world-class restaurants. Not to mention skiing, tobogganing, and ice skating in the winter. Plus, you can put your kayak in and paddle out to sea with the St. George River just down the road. The home is a beacon of comfort. All beds have luxury mattresses and four pillows. The bathroom on the main floor includes a large shower. The open kitchen is spacious and well appointed, including a lobster pot to have your own lobster festival! The generous kitchen table will accommodate eight with the accompanying chairs and the living room has plenty of seating to accommodate your whole family. A large laundry/mud room will give you more than enough room to park your muddy boots as well as all your adventure gear. There is a deck off the living room with a BBQ and chairs to enjoy the beautiful weather. The private half acre property is lined by blackberry bushes that you are welcome to pick in season. The long driveway accommodates four cars or your boat and trailer, and there’s easy access off routes Highways 1 and 90. Surrounded by trees Little Loon Farm is beautiful year-round and yes you can hear the loons in April, making it the perfect spot to base your Maine adventures. Things to Know Free high-speed WiFi Full kitchen Partially enclosed yard This home is heated by oil heat Snowbird-friendly *A doorbell surveillance camera is installed at this home. It face the driveway from the porch’s side door

Damariscotta Lakefront Retreat

Newcastle, ME, US
2 Bedrooms 4 Guests
Aug 30 - Sep 1
$429 night

Dock your boat at the private slip and enjoy the lovely confines of this Newcastle home. You get a lot of amenities at this comfortable, homey cottage. Downtown Newcastle is just five miles away but you’re right on lovely Damariscotta Lake with its myriad fishing and swimming spots. This two-level home has it all! The living room has a TV, vaulted ceiling, hardwood floors, a blue sofa, and beige recliners. The futon doubles as a sleeper and you can relax and gaze out on the water or head out onto the deck for some grilled goodies! Another seating area has a comfortable chair surrounding a wood-burning fireplace. The dining room has a table for six and the kitchen has a wealth of counter space, a white fridge, and range, among other accoutrements. Up to six guests will have their choice of two bedrooms separated by floors, as well as the available futon. The main-floor bedroom has a double bed and wood floors. There’s a full bath down the hall. The second-floor master has a queen bed, wood ceilings, and an en-suite bath with a standalone shower. You have a private washer and dryer, cable, internet access, and access to a family farm across the road. One dog is welcome in the home with an additional fee. Newcastle is a great place to get away from it all. Hike or bike along scenic trails or spend the day fishing or swimming on the lake. It’s peaceful and quiet. This lovely Midcoast Maine vacation home is the perfect refuge from the hustle and bustle of city life.

Kinney Cabin

Jefferson, ME, US
5 Bedrooms 11 Guests
Aug 31 - Sep 4
$708 night

Lakefront Elegance on Damariscotta Lake This 5-bedroom, 3-bathroom lakefront home on Damariscotta Lake offers the perfect blend of calm, comfort, and modern Maine cabin elegance. Step inside through a welcoming library and entryway, where a king-size pullout adds extra sleeping space, and continue into the dining area with seating for ten. The well-stocked kitchen with a pantry opens onto the deck, complete with a grill and outdoor seating. A full bathroom with walk-in shower connects to a first-floor queen bedroom with air conditioning and closet space, while a cozy sitting area nearby is perfect for game nights or simply taking in the lake views. Upstairs, the private master suite features a queen bed, air conditioning, closet, TV, and ensuite bath with a tub/shower combination. The lower level offers a second gathering space with a TV lounge, along with three bedrooms: one with twin bunk beds, one with a queen, and one with a king and lake views. Air conditioning keeps the space cool, and sliding doors lead to outdoor seating and a swinging bench. A full bathroom with walk-in shower and a convenient outdoor shower make it easy to clean up after a long day at the lake. The property’s outdoor spaces are designed for both relaxation and adventure. Enjoy morning coffee on the deck, rinse off under the outdoor shower, gather at the fire pit under the stars, or follow the winding, manicured path down to lakeside seating and a private dock. The shoreline features a quiet platform tucked among the trees - perfect for reading or simply soaking in the view - while the dock offers direct access to swimming, fishing, and boating. Guests are welcome to bring their own kayaks, canoes, or paddleboards, or arrange convenient rental drop-off through Midcoast Kayak. Located just minutes from Damariscotta Lake State Park and downtown Damariscotta’s shops, dining, and festivals, the home is also within 30 minutes of Pemaquid Beach and Lighthouse, with Camden, Rockland, Boothbay Harbor, Brunswick, and even Acadia National Park close enough for day trips. Portland International Jetport is under 90 minutes away, making travel seamless. With tasteful décor, colorful accents, and spaces designed for gathering and retreat, this lakefront home is an elegant yet welcoming escape for families and friends alike. **Please keep in mind the water depth at the dock is dependent on weather and drought conditions, the water depth is not guaranteed at the time of your stay. The dock is in the water mid-May to mid-October, weather dependent. The outdoor shower is only available until early October due to potential freezing temps.**

Sunset Cove

Saint George, ME, US
4 Bedrooms 8 Guests
Aug 28 - Sep 1
$573 night

Your Maine waterfront retreat on the serene St. George River. This 4-bedroom, 2.5-bath home offers sweeping water views, gentle breezes, and a front-row seat to Maine’s unforgettable sunsets. Relax on the farmer’s porch surrounded by landscaped gardens, or step inside to a sun-filled living room with large windows framing the river. The well-equipped kitchen features stainless steel appliances and everything needed for easy meal preparation, while the dining area is perfect for gathering with family and friends. The first-floor primary suite includes a king bed and peaceful water views. Upstairs, two additional king bedrooms provide comfort for guests, and a fourth bedroom offers a full and two twin beds—ideal for kids or extra visitors. An expansive deck is the heart of the home, where you can grill, sip a drink, and watch boats pass as the sun sets. A bright sunroom offers a cozy space for reading, games, or conversation. Just a short walk away, Fort Point Trail offers scenic hiking, and the surrounding villages are perfect for exploring. Rockland is minutes away with shops, galleries, and fresh seafood, while beaches and lighthouses are an easy drive. One well-behaved dog is welcome with prior approval. Sunset Cove is your home base for a relaxing, memorable Maine getaway—book your stay today. Dogs are considered, please contact us prior to booking with the age and breed of dog(s) for approval.

Quiet & Lovely Lakefront Cottage for Families!

Union, ME, US
3 Bedrooms 6 Guests
Aug 31 - Sep 2
$181 night

Escape reality and unwind at this classic 3-bed, 1-bath waterfront retreat in Union, Maine. With hiking closeby, a shared dock at your disposal, and Penobscot Bay just 15 minutes away, you’ll never suffer a dull moment at this cottage. You can pack your schedule with seeing baby puffins and catching boat tours, or simply hunker down and enjoy the lakefront life. This charming vacation rental is great for curling up with a book, cooking a family meals, and making memories that’ll last a lifetime! -- THE PROPERTY -- 1 Mi. to a Public Boat Launch | Waterfront Property | Exposed Wood Ceilings | Family Friendly Sleeping 6 and nestled up to the cozy waterfront of Sennebec Pond, this quaint abode is ready to host summer days at the lake with friends and family. Don't forget your paddleboards, kayaks, jet ski, or motorboat—there's a public boat launch only 1 mile away! Bedroom 1: Full Bed | Bedroom 2: Full Bed | Bedroom 3: Full Bed INDOOR LIVING: Open living space, breakfast nook with table, wood-burning stove, flat-screen TV, rustic interior decor OUTDOOR LIVING: Spacious deck, fire pit, waterfront views, direct pond access, shared dock, spacious outdoor area, charcoal grill KITCHEN: Well-equipped, stove, refrigerator, dishes & silverware, coffee maker, waffle iron GENERAL: Free WiFi, iron & board, linens/towels, complimentary toiletries, hairdryer, board games, books, central heating & air conditioning FAQ: Stairs required PARKING: Designated parking area on side of the road (2 vehicles) ADDT’L ACCOMMODATIONS: Traveling with more than 6? Reach out about the second vacation rental on site, Evolve listing 436933. Inquire about renting both properties together *NOTE: This is a quiet residential property that is best-suited for families, and is not an appropirate place to host raucus parties or large groups* -- THE LOCATION -- OUTDOOR FUN: Ayer Park (3.6 miles), Cramer Park (14.3 miles), Rockport Marine Park (14.5 miles), Thomaston Dog Park (15.6 miles), Harbor Park (17.5 miles), Camden Hills State Park (18.6 miles) BOAT/WATERSPORT RENTALS: Rockport Charters and Mooring Inc. (14.0 miles), Schooner Olad & Cutter Owl (17.1 miles), Evening Star Yacht Charters (19.9 miles), Ducktrap Kayak (21.1 miles) FOOD AND DRINK: Union Farmers Market (2.9 miles), Savage Oakes Vineyard & Winery (3.7 miles), Cellardoor Winery (18.2 miles) EVENTS: Banff Moutain Film Festival World Tour (14.7 miles), Main Restaurant Week (14.7 miles), Main Lobster Festival (17.3 miles) AIRPORTS: Knox County Regional Airport (20.9 miles), Bangor International Airport (60.1 miles), Portland International Jetport (81.8 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 - Please be respectful of the neighbors. Quiet hours are enforced from 10:00 PM to 7:00 AM - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This cabin is seasonal and only available to rent from May-October - NOTE: For your safety, there is no parking allowed over the septic system - NOTE: The water source is lake-fed filtered water, ideal for showering and washing dishes but not for drinking water - NOTE: This is a quiet residential property that is best-suited for families, and is not an appropirate place to host raucus parties or large groups - NOTE: The property requires stairs and may be difficult for guests with limited mobility

Sea Good

St. George, ME, US
2 Bedrooms 4 Guests
Aug 25 - 28
$669 night

Take in a truly stunning view of the ocean inlet, passing lobstermen, and the most beautiful sunsets you’ve ever seen from this waterfront home on the rocky shores of St. George. This is a place to spend your days swimming, hiking, and collecting sea glass on a private pebbly beach. Tucked into a thicket of coastal pines, this single-story, oceanfront home sits at the end of a quiet country road that’s wonderful for walking, jogging, and cycling. It’s a serene spot yet only seven miles south of Thomaston and 10 miles south of Rockland. There’s something to explore in every direction, whether you’re taking the ferry from Port Clyde to Monhegan Island, visiting the Marshall Point Lighthouse, or dining out in Rockland, Rockport, and Camden. Begin each day with a fresh cup of coffee outside on the brand-new, 50-foot deck, where you can listen to the waves lap up to the shore and watch the morning sun illuminate the surrounding conservation land. There’s a gas grill and ample outdoor seating for lunchtime barbecues, a screened porch where you can retreat with a good book in the afternoons, and a firepit for roasting marshmallows with your loved ones beneath the stars. Inside, the house has been beautifully renovated with new wood floors, new furnishings, and magnificent ocean views highlighted at every turn. Enjoy a lovely living room with a smart TV, an oceanfront dining space, and a kitchen outfitted with stainless steel appliances (including double ovens and a gas stove), a vintage New England farmhouse sink, and such bonus tools as a Le Creuset Dutch oven and a seafood cooker. High-speed WiFi allows everyone to stay connected and share prized moments during their stay. The home is also particularly magical for children, offering endless spots to explore as well as an assortment of games, toys, a high chair, a booster seat, a white noise machine, room-darkening shades, a Pack ’N Play, and bunks in one of the bedrooms. The other bedroom is a primary suite that opens to the deck. 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. The wood stove is currently inoperable and not for guest use.

Evelyn’s River Front Retreat

Cushing, ME, US
4 Bedrooms 8 Guests
Aug 24 - 27
$526 night

Escape to this stunning riverfront house nestled on 13 acres of picturesque land in Cushing, ME. Recently renovated, this spacious home boasts a modern interior with brand new bathrooms, a fully equipped kitchen, and convenient washer/dryer. With 4-season climate control, including AC and heat, along with high-speed WiFi, this property offers the perfect blend of comfort and convenience. Step outside and explore the walking trail that leads directly to the tranquil St. George River, where you can enjoy peaceful moments by the water’s edge. The expansive deck provides a perfect spot to take in the river views, while the patio furniture invites you to relax and unwind in the serene surroundings. Inside, the house is thoughtfully equipped with amenities to enhance your stay, from cozy bedding options including a king bed, queen bed, double bed, twin bed, and bunk bed, to family-friendly features like a Pack-N-Play for the little ones. The fully stocked kitchen includes everything you need to prepare delicious meals, from a coffee maker to a dishwasher, while the spacious living room offers a comfortable retreat with TV and board games for entertainment. Whether you’re seeking a peaceful retreat or a base for outdoor adventures, this riverfront property in Cushing is the perfect choice. With its idyllic setting, modern comforts, and easy access to nature, this home invites you to create unforgettable memories with your loved ones. Book your stay today and experience the beauty of Maine’s St. George River firsthand.

Beehive Cottage

Cushing, ME, US
1 Bedrooms 2 Guests
Aug 24 - 28
$669 night

The Bee Hive offers a serene and romantic retreat with panoramic ocean views, perfect for couples seeking a peaceful getaway. This cozy cottage combines modern comforts with coastal charm, creating a warm and inviting atmosphere ideal for relaxation and romance. ​​​​​​​Inside, you’ll find a beautifully decorated living space with a charming coastal flair. The cozy bedroom features a queen bed, ensuring restful nights after a day of exploration. Unwind with a soak in the elegant freestanding tub or curl up by the fireplace in the living room—perfect for intimate evenings. The fully equipped kitchen includes stainless steel appliances, making it easy to enjoy home-cooked meals. Step outside to the private deck and breathe in the fresh ocean air as you listen to the soothing sounds of the sea and watch the sun dip below the horizon. Whether you’re sipping wine on the deck or taking in the view from your window, the peaceful atmosphere of The Bee Hive will leave you feeling recharged and connected. Though tucked away for ultimate privacy, the cottage is just a short drive from charming coastal towns, hiking trails, scenic lighthouses, and romantic dining options—everything you need for a memorable date night or afternoon adventure. Acadia National Park is just two hours away, making it a great home base for exploring one of Maine’s most iconic destinations. The Bee Hive is your perfect escape—whether you’re seeking a romantic weekend, a tranquil retreat, or simply a place to relax and enjoy each other’s company. Book your stay now and experience the magic of Maine at this charming oceanfront cottage. Let the beauty of the coast and the gentle sea breeze whisk you away on a vacation you’ll never forget.

Seegar Camp

Saint George, ME, US
2 Bedrooms 6 Guests
Sep 27 - 29
$484 night

A Nature-Lover’s Retreat on the Water Welcome to Seegar Camp, a newly renovated two-bedroom, one-bath cottage that blends rustic Maine charm with modern comfort. With wood paneling and original flooring throughout, the cottage exudes warmth and character, while large windows fill the space with natural light, sea breezes, and sweeping views of the water and surrounding landscape. The open living and dining area offers panoramic vistas, cozy seating, and tasteful décor that mixes antiques with modern touches. A wood stove creates the perfect ambiance on cooler evenings (usage is per request based on experience), while a 50" SmartTV, sectional couch, and a collection of games make movie nights and family gatherings easy to enjoy. Upstairs, the loft provides a flexible retreat with a trundle bed (two twins), quiet workspace, or game room. For added comfort, a wall-hung unit provides both heating and air conditioning, making the space enjoyable in every season. The kitchen is thoughtfully outfitted with stainless steel appliances and all the essentials for preparing meals, while two main-level bedrooms, each with a queen bed, provide restful comfort after days spent outdoors. Step outside to a landscaped natural oasis featuring a deck with sweeping water views and an outdoor table and chairs for al fresco dining; fire pit surrounded by Adirondack chairs, shaded sitting areas, and 200 feet of shared shoreline. Spend your days paddleboarding, swimming, or simply unwinding by the water’s edge. Please note: Seegar Camp shares one acre, the stairs to the water, the platform with Adirondack chairs, and shoreline access with the neighboring Lindquist Cottage. The two properties are connected by a manicured walkway and can be rented either together for larger groups or separately for a more private escape. Nestled in Tenants Harbor, this serene retreat offers both privacy and convenience. From here, you’re just 15 minutes from Rockland’s vibrant art galleries, museums, and waterfront dining, and only 25 minutes from Camden, where you can enjoy harbor sails and breathtaking hikes. The charming village of Thomaston is just 10 minutes away, while the Monhegan Ferry Terminal is a quick 5-minute drive - your gateway to one of Maine’s most iconic offshore islands. For lighthouse lovers, Marshall Point Lighthouse, made famous in Forrest Gump, is also just 5 minutes away. And if you’re looking for a bigger adventure, Acadia National Park and Bar Harbor are about 2 hours to the north, perfect for a memorable day trip. Seegar Camp is the perfect place to slow down, recharge, and reconnect with nature — all while enjoying modern amenities and the unmatched beauty of Maine’s outdoors. One pre-approved dog is welcome with an additional fee - please inquire.

Waterfront Cottage! Family-Friendly Hideaway

Bristol, ME, US
2 Bedrooms 6 Guests
Aug 24 - 26
$199 night

Dual-Level Decks w/ Water Views | Remote Work Friendly | 11 Mi to Pemaquid Lighthouse | Monhegan Island Day Trips This idyllic vacation rental in Round Pond pairs a quiet woodland setting with breathtaking waterfront views, offering a peaceful coastal sanctuary! Embark on an island excursion with Hardy Boat Cruises or savor world-class seafood at Shaw's Wharf. When it's time to unwind, cap off your day with an evening cocktail on one of the decks. Book your Midcoast Maine getaway. -- THE PROPERTY -- HOME FEATURES - Open-concept living & dining area - Upper & lower decks w/ seating - 2 dedicated workspaces - 3 Smart TVs - 6-person dining area - Board games, books - Wood-burning stove - Washer & dryer - Window A/C units KITCHEN - Refrigerator, microwave, stove/oven, dishwasher - Cooking basics, dishware/flatware - Drip & Keurig coffee makers (starter pods provided) ACCESSIBILITY - Multi-level home, 5 steps to enter - All bedrooms on 2nd floor & basement floor FAQ - The property does not have central air, however it is equipped with window A/C units PARKING - Driveway (3 vehicles) -- THE LOCATION -- - Charming coastal village setting, walk to Muscongus Bay shoreline - 5 miles to LaVerna Preserve - Hiking Area - 7 miles to Shaw's Fish & Lobster Wharf - 7 miles to Hardy Boat Cruises (ferry to Monhegan Island) - 8 miles to Pemaquid Beach - 10 miles to Downtown Damariscotta - 11 miles to Newcastle & Pemaquid Point Lighthouse -- 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 - Multi-level home, 5 steps to enter - All bedrooms on 2nd floor & basement floor - The property does not have central air, however it is equipped with window A/C units

White Caps

Saint George, ME, US
3 Bedrooms 6 Guests
Aug 24 - 27
$564 night

Welcome to White Caps, a beloved oceanfront home nestled along the scenic shores of Port Clyde Harbor. For more than 40 years, this enchanting cottage has welcomed families seeking a peaceful Maine getaway where time slows down and memories are made. Just a short walk from the iconic Marshall Point Lighthouse—famously featured in Forrest Gump—White Caps captures the essence of a traditional Maine vacation with its rustic charm, expansive ocean views, and welcoming atmosphere. A Tranquil Setting with a Rich History Located on a serene private road and surrounded by multigenerational family homes, White Caps offers a cozy, inviting atmosphere filled with antique furnishings and timeless character. It is a comfortable retreat designed for relaxation and an appreciation of the natural beauty surrounding it. Breathtaking Views and a Prime Location Wall-to-wall windows showcase stunning views of the Atlantic Ocean and bring the beauty of the coastline indoors. Watch boats drift by and the tides roll in from the rocky shoreline just outside. A short stroll brings you to Marshall Point Lighthouse, where you can enjoy some of Maine’s most iconic coastal scenery. Whether sipping your morning coffee on the deck or enjoying dinner at sunset, White Caps offers a front-row seat to unforgettable views. Spacious, Comfortable Living Inside, the open and inviting living areas are designed to maximize the panoramic ocean views. The living room and sunroom provide ample seating and wonderful vantage points for watching boats travel through the harbor. The well-equipped kitchen makes meal preparation easy, while the dining room offers a welcoming space to gather for meals with family and friends. Comfortable Bedrooms for Restful Nights The second floor features a primary bedroom with a queen bed, one bedroom with a double bed, and another with two twin beds. A cozy den with a futon provides additional sleeping space or a quiet place for reading and relaxing. The cottage offers a comfortable balance of privacy and togetherness for families and groups. Summer Fun in the Bunkhouse During the warmer months, guests can enjoy the small bunkhouse located on the property. With two twin beds, it is a fun retreat for older children or young adults who would like a little independence while remaining close to the main house. Additional Space for Larger Families For guests seeking more room, Little White Caps—a separate apartment above the garage—may be available to rent. This charming addition provides extra living space for larger families or groups while offering a balance of privacy and proximity to the main house. Endless Activities and Local Charm Explore Marshall Point Lighthouse, stroll along the coast, or spend a quiet day enjoying the house and its surroundings. Port Clyde is rich in character and history, with nearby trails, shops, art galleries, and seafood restaurants to discover. Local beaches are also just a short drive away for swimming, sunbathing, shell collecting, and coastal adventures. Book your stay at White Caps and experience the magic of this beloved oceanfront retreat. Whether you are savoring sunsets from the deck, exploring the beautiful Maine coastline, or relaxing in the comfort of this charming cottage, your next family vacation awaits. Please note: Exterior security cameras are located on the property.

Driftwood

St. George, ME, US
3 Bedrooms 6 Guests
Sep 7 - 9
$551 night

Driftwood is one of those places - both in form and function - that feels distinctly Maine. Maybe it’s the pristine waterfront location at the end of a winding, private road just a mile or two from Port Clyde. Or perhaps it’s the way the house itself feels, thanks to an abundance of windows, clean lines, and a true sense of peace and quiet. Whatever it is, Driftwood is everything a stay in Maine should be. A full deck (new in 2024 with new deck furniture as well) is a great place to overlook the vast, saltwater St. George River makes this space as comfortable for two people as it is for six. The first floor is more or less an open-concept space, with a comfortable living room that flows easily into the dining area with seating for six. Access to the front deck is right here as well, where you’ll find plenty of outdoor seating, a grill, and just about the nicest views you could ever want at any time of day. The galley-style kitchen includes a full-size gas stove and a dishwasher, and it’s well-equipped for meal preparation. The primary bedroom is also on this floor, tucked away at the back of the house in a sunny, spacious spot. Upstairs, find two more bedrooms, both of which are bright and sunny with beds close to the windows, so you can hear the water lap on the shore as you fall asleep. The shore is easily accessible by a well-worn path - the owners of Driftwood report this area is just right for kayaking and paddleboarding. The villages of Port Clyde and Tenants Harbor are both within a few minutes’ drive, with Sandy Drift Inn Beach minutes away as well. Things to Know Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide by The Good Neighbor Policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises. Fires are not permitted at this property without explicit permission.

Chimerique on the Water

Saint George, ME, US
4 Bedrooms 12 Guests
Sep 26 - 29
$847 night

Classic Maine Coastal Chimerique: Your Dream Summer Getaway On the water in Midcoast Maine Nestled on a private property overlooking Southern Island and the enchanting Eel Grass Cove in Tenants Harbor, this classic Maine home offers stunning panoramic ocean views and the perfect escape for creating lifelong memories. Perfect for larger groups or families, but also ideal for a weekend getaway in the spring or fall. Welcome to Chimerique, where whimsical meets wonderful. Surrounded by towering pines, this serene retreat provides the privacy you crave in beautiful Midcoast Maine. Relax on the expansive decks that stretch across the length of the house, soaking in breathtaking harbor vistas and the soothing sounds of gentle waves. It’s the ideal setting for al fresco dining with family and friends. A natural path leads to the shoreline, where you can launch a kayak or take a refreshing swim in the cool Maine waters, perfect for adventurous spirits. Step inside to find a luxurious primary suite with an ensuite bathroom and jacuzzi tub, conveniently located on the first floor along with additional bedrooms for easy access. The well-stocked kitchen, outfitted with stainless steel appliances, is ready for larger groups and memorable meals, while the formal dining area provides an inviting space for gathering. Mornings are magical here; sip your coffee at the breakfast table as the sunrise lights up the harbor. Just beyond the kitchen, a small laundry room leads to a cozy sunken living room with ample seating for everyone to unwind. There is also a formal dining area for shared meals and memories. Down the hall, you’ll find a guest bathroom, two comfortable bedrooms, and a shared full bath. Upstairs, a spacious semi-divided bunk room accommodates 4–6 guests and includes its own ensuite bathroom. On rainy evenings, head downstairs to the unfinished basement where a game room with a billiards table offers fun and relaxation for the whole group. Experience the charm and tranquility of Chimerique—your dream summer retreat awaits. First Floor: Master Bedroom, Water Side, Queen, Ensuite with Jacuzzi and shower Guest Bedroom, Water Side, Queen Shared full bathroom Half Guest Bathroom Guest Bedroom, Road Side, Two Twins Second Floor: Additional sleeping area: Two Doubles and Two Twins, Ensuite full bathroom with club foot tub/shower Pets: Dog allowed with pre-approval- please inquire.

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Vacation Rentals Near Waldoboro

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