Large group vacation rentals in Round Pond, ME

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

Get ready to enjoy spectacular sunsets and peaceful nights at this warm and inviting beach house in the sought after Seawood Park Community in Bristol. Spread out over two well-appointed stories, this wonderful home features a well-equipped, full kitchen, two dining tables for meals, rainy day games, or laptops, and two distinct living areas. Step outside onto the first-floor deck and take in west-facing glimpses of Johns Bay and Rutherford Island. When you want to get out and explore, make your way to the nearby walking path that runs along the shoreline and leads to a private sand beach. THINGS TO KNOW Beach towels included.

Cozy, private, and beautifully situated near the banks of the Damariscotta River, the Charming South Bristol Cottage offers the quintessential Maine experience in one of the Midcoast’s loveliest towns. In the same family since 1947, this home is a wonderful place to make memories, whether you’re curled up by the fire in the mornings and evenings, watching the waves crash at Pemaquid Point, walking in South Bristol and Christmas Cove, or picking up lobster fresh from the boats in town. It’s the way life should be! What’s nearby: South Bristol is a classic Maine town - an active lobstering village with friendly, welcoming people and stunning vistas. You’ll experience the relaxing intimacy of a small town with access to plenty of tourist sites and activities, including kayaking, hiking, fishing, charter boat tours, shopping, and dining close by. You can pick up incredibly fresh lobster at the South Bristol Fisherman’s Co-op half a mile east, take a dip in the brisk waters of Pemaquid Beach 11 miles east, or enjoy a beautiful day trip to Camden, Boothbay Harbor, or Monhegan Island. Things to know: Free WiFi Full kitchen

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.

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.

Paradise awaits at this beautiful, two-story home conveniently located on a dead-end street near the East Boothbay Village! This is the perfect spot to bring family and friends and experience a truly relaxing and memorable escapade. You will be a short three-mile drive from Boothbay Harbor, where numerous restaurants and marinas await. Discover amazing attractions within a short drive, including Boothbay Harbor Country Club, Coastal Maine Botanical Gardens, Maine State Aquarium, Chocolate Church Arts Center, Maine Maritime Museum, Pemaquid Beach Park, and Fisherman Museum. This splendid retreat boasts a beautifully decorated open floor plan that seamlessly combines all living spaces into one. Spread out comfortably in the living room, furnished with an extensive sofa, a wood stove, and a smart TV with streaming services to keep you entertained during your stay. When mealtime comes, put on the chef’s apron and prepare exquisite homemade meals for your crew in the well-appointed, open kitchen, complete with all the major appliances to whip up everything that comes to mind. The living area opens onto a screened porch offering impressive views of the Damariscotta River and a wonderful spot to dine alfresco. The adjoining open deck is also a fantastic spot to take in the marvelous river views. Another great perk is the access to a shared beach and dock at the residence, which are shared with 2-3 neighboring homes. Additional perks include a gas grill, a washer/dryer, high-speed WiFi, and a soaking tub. 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.

Escape to a new and secluded cabin in the woods in charming Boothbay. This spacious 4BR/3BA home offers comfortable accommodations for your group of 15. Feel right at home in the open-concept living area with vaulted ceilings and warm wood paneling, and step out to a wraparound deck with open-air dining. Soak up rich maritime history in East Boothbay, or discover eclectic shopping and waterfront dining in Boothbay Harbor - both just minutes from your door. ABOUT THE CABIN The open-concept kitchen, living, and dining area is both spacious and cozy, with soaring ceilings and knotty pine paneling. Settle as a group onto the inviting sofas (one converts to a queen sleeper) and plush armchair to swap stories from the day’s adventures in Boothbay Harbor, or step out to a sprawling, wraparound deck with reclining lounge chairs, and open-air dining for seven. The second living area is configured with a queen sleeper sofa. Prepare family meals in the luxe kitchen with granite countertops and stainless steel appliances, including a French-door fridge. Or lend the chef a hand at a center island bar with seating for four. Bay windows lend sunlight and sophistication in the dining area, where a wood table is a lovely gathering spot for eight. BED & BATH The master suite boasts a king bed, twin sleeper chair, massive walk-in closet, sliding door access to the deck, a Peloton bike, and a TV. Get some work done at a wood writing desk, and refresh in the private en-suite bathroom with soaking tub and glass shower. Upstairs, find three additional bedrooms with full closets. The second guest room includes two twin beds and a twin trundle. The third bedroom has three twin beds. The fourth room is outfitted with a comfy queen bed. A guest bathroom on the main level features a shower and pedestal sink, while the second-floor bathroom has a tub/shower combination. EXTRA AMENITIES & DETAILS Your reservation at this wooded retreat includes complimentary Wi-Fi, a washer/dryer, and parking for four cars. Please note that a 4WD vehicle is required to access this property during the winter months. LOCATION Nestled in the trees on a quiet wooded lot, this secluded log cabin is ideally located just 10 minutes from the heart of Boothbay Harbor. Give the cook the night off and dine at Lobsterman’s Wharf, a casual seafood tavern with a waterview deck just a 5-minute walk away. Soak up maritime history in the village of East Boothbay with a rich shipbuilding heritage. Then, head to East Boothbay General Store for lunch fare and fresh baked goods.

Come relax on this gorgeous slice of unspoiled Maine coast at this oceanfront cabin with multiple rocky beaches nearby. There is a deep water dock perfect for sunbathing, swimming, or fishing, and the cabin’s interior features a rustic, wood-paneled design with high rafters and an open living and dining space. You will enjoy modern amenities such as WiFi, TV, music, and plenty of fun games. There is one newly renovated bathroom with a cheery red floor, a pedestal sink, and a new shower. What’s nearby: There are many nearby trails that are part of the Boothbay Land Trust. A short drive brings you to downtown Boothbay Harbor, where you will find many fine restaurants and shops, a great aquarium, and the amazing Coastal Maine Botanical Gardens. Things to know: Free WiFi Full kitchen Coin laundry - laundromat in town

Vannah Lane is a delightful house located on coveted Horse Point Road in Port Clyde. Nestled in the tall pines just past the famed Andrew Wyeth summer home, Vannah Lane sits on three private acres and 350 feet of water frontage. This house provides the best Port Clyde has to offer. You’ll have peace and quiet, just a walkable distance from the village for your morning coffee. Catch the ferry to Monhegan or attend an art studio opening, followed by a waterside dinner. The classic clapboard cape is situated on a knoll, surrounded by a well-manicured lawn and overlooking Deep Cove and Howard’s Head. A path meandering through trees and mossy boulders takes you to a small beach, perfect for laying out a blanket and spending the day searching for sea glass, watching for wildlife, reading, or launching a kayak or canoe. When the tide is low, guests can explore the rocks and search for crabs under the seaweed. This is an open-concept house with two bedrooms, a great room, a dining area, and a finished loft area above the first floor. The dining room looks out onto the deck, the lawn, and the water beyond the trees. French doors open onto the deck where you’ll find a gas grill and seating to take in the water views. The kitchen is modern with plenty of counter space and modern appliances including a full-sized stove, a dishwasher, a microwave, a toaster, and a coffee maker. The vaulted-ceiling great room is the heart of the house. Large and beautiful windows let in natural light throughout the day. Free Wifi allows for laptop use in the house or on the deck, and there is a TV with streaming access. Off the dining area, you’ll find the primary bedroom - this room is very private with an en-suite bathroom and views of the woods and the water beyond. This bedroom has a new queen bed. Upstairs, you’ll find the second bedroom with a queen bed. A full bath is located between this bedroom and the loft area. The loft area, open to the rooms below, offers a double bed and a work area for guests working remotely. There is a washer and dryer available for guest use as well. 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. Fires are not permitted on this property.

A wonderful home base for exploring Midcoast Maine, this tree-lined property in Damariscotta offers every comfort of home in a lovely woodland setting. Serene rivers, charming villages, the rocky ocean shore - it’s all at your fingertips here. This two-story home sits a few blocks off Maine Route 1 in Damariscotta, just over two miles from the restaurants, pubs, and conveniences in the heart of town. It’s an incredibly central Midcoast location, whether you’re hoping to snack on lobster rolls in Wiscasset (11 miles), drive down to the Pemaquid Point Lighthouse (18 miles), or set sail from Boothbay Harbor (19 miles). Rockland, St. George, Rockport, and Camden are all within 25 miles as well. Come home from the day’s excursions to relax on the screened porch and light the gas grill for an evening barbecue. There’s a well-equipped kitchen with stainless steel appliances to assist, a window-lined dining room where you can sit down to dinner, and a high chair and booster seat provided for your little ones. In the evenings, kick back on the sofa and stream your favorite movies on the living room’s smart TV, or retreat to one of the two desks (in the dining room and the basement) to log onto the high-speed WiFi. Additional features of the house include TVs in the bedrooms, a private washer/dryer, and split AC throughout. THINGS TO KNOW The fireplace is not available for guest use.

An exceptional stay awaits at this tranquil vacation home. Tucked into the woods for privacy and just 1/2 mile from the water, this one-bedroom rental has everything you need for a relaxing getaway to Midcoast Maine. Relax and unwind on the wrap-around deck or fire up the gas grill for a backyard barbecue. Enjoy private access to the ocean via the association, with a dock, float, beach, and waterfront picnic area with beautiful views of Linekin Bay all just a half-mile from the home. Bright and inviting, the interior offers an open floor plan with strong natural lighting and all the comforts of home. The kitchen comes equipped with a full suite of stainless steel appliances, including a dishwasher, for easy home-cooking and stress-free cleanup. After the day’s adventures, cozy up in the living room and unwind with your favorite shows and movies on the smart TV. Modern must-haves include free WiFi. WHAT’S NEARBY A short drive into the town of Boothbay Harbor offers many local attractions, including the Opera House with live concerts, the Carousel Theater, whale watching, boat rides, harbor tours, trolley rides, kayaking outfitters, unique stores for shopping, and a great selection of local bars and dining, plus a movie theater and the Hannaford supermarket. The Boothbay Region Landtrust offers a wide variety of hiking trails on the local land preserves. Other favorite attractions are Southport and Hendrick’s Head beach, Lighthouses, Boothbay Railway Museum, Ocean Point scenic drive. Pemaquid Point Lighthouse and beach, Reid State Park, and Popham Beach are all an easy day trip away. Please check with our local Chamber of Commerce and the Boothbay Region Land Trust for everything this region has to offer.

Newly Renovated In 2025. Linekin Bay Lookout is a private East Boothbay deckhouse set above Linekin Bay, where pines, tidewater, and sunset light define the stay. This 3-bedroom, 2-bath home pairs classic Maine warmth - vaulted wood ceilings, exposed beams, broad windows, and wood floors - with the simple pleasures guests come here for: coffee on the deck, seafood on the grill, and a private wooded path through the pines to the rocky tidal shore. The upstairs living level is the heart of the home. The living room looks out toward the bay and opens to the long second-floor deck, which connects the living area and primary bedroom. Gather under the vaulted ceiling, cook in the adjacent kitchen, linger over dinner by the glass doors, or, after a day on the water, step outside to watch the sun set over Linekin Bay. The home sleeps up to five guests. Upstairs, the primary bedroom has a king bed, deck access, bay views, a dressing area, and a newly updated bathroom with a tiled walk-in shower. Downstairs are two additional bedrooms - one queen and one double - plus a second updated full bath, laundry room, and family room, giving couples, small families, or friends on a quiet getaway room to gather and space to retreat. The setting feels secluded but still connected. Pick up freshly baked muffins or cinnamon buns from East Boothbay General Store just down the road, head into Boothbay Harbor for restaurants, shops, boat tours, whale watching, and harbor walks, or spend the day at Coastal Maine Botanical Gardens. Head to Ocean Point for classic coastal walks, salt-air views, ocean swims, and a glimpse of Ram Island Light, guarding the eastern entrance to Boothbay Harbor and the mouth of the Damariscotta River. ​​​​​​​Bigelow Laboratory is also within walking distance of the home, making Linekin Bay Lookout a practical and peaceful East Boothbay base for visiting scientists, researchers, public-event guests, seasonal staff, and others spending extended time in the region. With Wi-Fi, Ethernet, a dedicated workspace, and a quiet setting among the pines, the home is also well suited to remote work, writing, reflection, or a longer coastal stay. Good to know: The shoreline below the home is private, natural Maine coast - rocky and tidal rather than sandy. It is a beautiful place for tide-watching, rock-hopping, and quiet time by the water; water shoes are recommended for low-tide exploring.

Spread out between multiple sitting areas, a spacious kitchen, and three floors at this expansive 4BR/3.5BA East Boothbay home. Outdoors, a sprawling deck, gazebo, and gorgeous garden offers an outdoor haven for dining and sunny-day relaxation. The third floor also has a widow’s walk offering a view towards the ocean. Drive 10 minutes to Boothbay Harbor, the Coastal Maine Botanical Gardens, or 15 minutes to the Boothbay Harbor Country Club. You’re also under a 10-minute stroll to the acclaimed Carriage House Restaurant, offering a modern menu of New England-inspired dishes. ABOUT THE HOUSE There’s a fresh coastal feel throughout this stylish home, offering a relaxing home base after a day of outdoor fun. Curl up on the sectional sofa or cushioned chairs in the main sitting area. Opposite, a bookshelf contains an entertainment center with a 48’ flat screen TV. Steps away, chairs and couches furnish two additional sitting areas — perfect for group chit-chat and planning day trips. The chef in your group will love the large and contemporary kitchen, complete with a full suite of stainless steel appliances. The kitchen is a great social space too, with a central island seating three. Share sit-down meals around the eight-person dining table. A sprawling deck overlooking the garden boasts cushioned chairs and a six-person dining table for al fresco meals. A wooden walkway leads to a gazebo, where another dining table seats four. There’s also a gas grill for afternoon barbecues. The home is spread across three floors, with total sleeping space for 12 guests. On the entry-level, the master suite features two queen beds and ample storage space. Guests here have their own en-suite bathroom with a walk-in shower. Upstairs, garden views and a glimpse of the ocean await in a second bedroom featuring a king bed, two comfy chairs, and a private deck with a table seating two. An en-suite bathroom has a walk-in shower. A third bedroom offers the same impressive views, a plush queen bed, and a chaise lounge. The kid-friendly fourth bedroom comes with two twin-over-twin bunk beds. On the top floor, a bonus living/sleeping area offers the best ocean views in the house. A daybed (with a trundle beneath) and two sitting chairs furnish this tucked-away space. The house also has a guest bathroom with a tub/shower combination and a half bath. Extra amenities include complimentary Wi-Fi, cable TV, and a washer/dryer. Driveway parking is available for four cars. THE LOCATION This East Boothbay home overlooks Linekin Bay, with adjacent walking trails leading to Linekin and Burley Preserves. Just a 10-minute drive away, Boothbay Harbor offers boating, sailing and fishing trips. Head to Cap’n Fish and search for whales surfacing along the Maine coastline, or book trips aboard the Schooner Eastwind to visit the Burnt and Ram Island lighthouses. For a special evening meal, book a table at Carriage House Restaurant (an 8-minute walk) for craft cocktails and upscale New England comfort food.

Pets Welcome w/ Fee | Cookout Ready | Near Public Kayak & Canoe Launches Nestled between Damariscotta River and Linekin Bay, this bright 3-bedroom, 2-bathroom home is perfect for rejuvenating waterfront adventures! Walk to the marina or take a short drive to the scenic Ocean Point Walk. Back at the vacation rental, unwind in the cozy living area or soak in stunning views of the Damariscotta River from the front porch. Your leisurely East Boothbay stay awaits! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed  - Bedroom 2: 1 queen bed - Bedroom 3: 1 queen bed, 1 lofted twin XL bed OUTDOOR LIVING  - Deck, outdoor dining table, rocking chairs, water views - Gas grill (seasonal) - Front porch INDOOR LIVING  - 4 Smart TVs - Board games, books - Kitchenette w/ microwave, refrigerator, sink - Dining table, breakfast bar - Chandeliers MAIN KITCHEN - Stove/oven, refrigerator, microwave - Keurig coffee maker, toaster - Dishware/flatware, cooking basics - Trash bags/paper towels GENERAL   - Free WiFi  - Mini-split air conditioning/heat - Linens/towels, hair dryer - Washer/dryer, iron/board - Keyless entry FAQ - Homeowner on-site (backyard cabin) - Pet fee (paid pre-trip) ACCESSIBILITY - 2-story home, step to enter  - Bedroom & full bathroom on 1st floor - Main living room & kitchen on 2nd floor PARKING - Driveway (3 vehicles) - Street parking -- THE LOCATION -- - Walk to general store - 4 miles to Ocean Point Walk - 20 miles to Pemaquid Point Lighthouse - 6 miles to Boothbay Railway Village Museum - 63 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 - Pet friendly w/ $75 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 a step to enter. The main living room and kitchen are located on the 2nd floor - A bedroom with a kitchenette and en-suite bathroom is located on the 1st floor and requires an exterior door to access - The homeowner may be on-site in a separate cabin located in the backyard, with the entrance facing away from the main property - The gas grill is available in the summer months Licence number: 0179

2 Mi to Cap'n Fish's Whale Watch | Cozy Wood-Burning Fireplace Craving an escape where water adventures meet laid-back living? This Boothbay Harbor vacation rental cabin in Sprucewold delivers a true taste of Maine! Spend beach days swimming and tide pooling, fire up the grill for sunset feasts on the deck, and browse the village’s renowned art galleries just down the street. With 2 bedrooms, 1 bath, and all the essentials, this home is perfect for couples or small groups looking to explore! -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 2 twin beds INDOOR LIVING - Flat-screen TV - Dining table, sofa seating - Remote-controlled gas fireplace OUTDOOR LIVING - Deck, outdoor dining - Gas grill - Front porch KITCHEN - Refrigerator, stove/oven, microwave - Cooking basics, dishware & flatware - Drip coffee maker, toaster GENERAL - Free WiFi - Mini-split A/C & heating units - Linens/towels, complimentary toiletries - Hair dryer ACCESSIBILITY - Single-story cabin, 5 steps to enter PARKING - Gravel driveway (4 vehicles) ADDT’L ACCOMMODATIONS - There is an additional property available down the street with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- - 2 miles to Lobster Cove Preserve - 2 miles to Sweet Action Charters - 4 miles to Maine State Aquarium - 5 miles to Gregory Hiking Trail - 62 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 single-story cabin requires 5 steps to enter

Retreat into the romance of coastal Maine at this exquisite Boothbay Harbor vacation rental that bursts with vintage character and seaside charm. Your harbor-view gem comprises two separate three-level homes. You’ll love the antique decor and original 1800s wood floors, while modern amenities include updated kitchens and smart TVs. Across the street, you’ll find sunset chairs with the best footbridge view in town. Stroll to the pier, waterfront parks, and tasty dining options. Pack your binoculars for Cap’n Fish’s Whale Watching, climb aboard the Windjammer Eastwind, or rent a seafaring vessel at Schooner Eastward. Boothbay Harbor Country Club and Coastal Maine Botanical Gardens are within a short drive. Captain’s Quarters’ modern living area presents a Sonos system and a large 4K smart TV with access to Netflix, Hulu, Apple TV, and all of today’s online entertainment. Prepare delicious dishes in the convenient full kitchen, configured with a small eat-in table and a larger nearby dining table. Sleep soundly in the primary suite that has an en suite bathroom that is also accessible via the hallway. One of the guest bedrooms includes a telescope for harbor gazing. All bedrooms provide a smart TV, bedside USB charging, and a Bluetooth music system. Head of the Harbor has an inviting living area with twin and queen sofa beds. The 4K smart TV provides access to Netflix, Hulu, Apple TV, and other services. A large farmhouse sink and an eat-in table highlight the beautifully updated kitchen. The gas grill on the deck is perfect for sunny afternoon cookouts. The bedroom occupies the entire top floor and features a charming antechamber with a window air-conditioning unit. Extra perks include complimentary commercial-grade WiFi and a backup generator. Each home is equipped with a private washer/dryer. THINGS TO KNOW The homes are not directly connected.

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.

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.

Welcome to your perfect getaway in Boothbay, ME! This newly built, charming home is designed for family-friendly fun and relaxation. Step onto the spacious deck, complete with patio furniture and a gas grill, ideal for enjoying warm summer evenings. After a day of exploring the beautiful coastal scenery, unwind in the hot tub while soaking in the serene surroundings. Inside, discover a newly equipped kitchen with modern appliances—fridge, stove, oven, and microwave—making meal preparation effortless. The cozy living room invites family gatherings, featuring a TV with cable for entertainment. Comfortable sleeping arrangements are provided to ensure a restful stay for all. Conveniently located just steps from the ocean and a short distance to town, you’ll have easy access to local restaurants, shops, and attractions. Enjoy bird watching, scenic drives, and hiking amidst Boothbay’s stunning autumn foliage. Equipped with amenities like WiFi and a washer/dryer, this home ensures a comfortable and relaxing stay. Book your visit today and create unforgettable memories in this beautiful coastal retreat!

Captain’s Quarters | Historic Coastal Luxury in the Heart of Boothbay Harbor Experience the perfect blend of historic New England charm and modern luxury at Captain’s Quarters, a beautifully restored 1800s cottage nestled in the heart of Boothbay Harbor. Overlooking the iconic footbridge and located directly across from the harbor, this elegant retreat offers a front-row seat to one of Maine’s most beloved coastal destinations. Step outside and immerse yourself in the vibrant harbor atmosphere. Downtown shops, restaurants, galleries, and waterfront attractions are just a short stroll away. Enjoy a leisurely brunch at a local favorite, indulge in a relaxing spa treatment nearby, or take in the spectacular harbor sunsets from the Adirondack chairs located across the street. For adventure seekers, golf courses, sailing excursions, whale-watching tours, harbor cruises, and boat rentals are all within easy reach. Inside, the home seamlessly combines classic architecture with contemporary comforts. The inviting living area is designed for relaxation, featuring comfortable furnishings, a Sonos sound system, and a 55-inch 4K Smart TV with access to Netflix, Hulu, Apple TV, and other popular streaming services. The well-appointed kitchen makes meal preparation a pleasure, offering modern appliances, ample workspace, and a dishwasher for easy cleanup. Guests may also enjoy the shared outdoor patio area with a gas grill, perfect for casual summer cookouts. Spanning three levels, each bedroom is thoughtfully equipped with its own Smart TV, Bluetooth music system, and convenient USB charging stations. The primary suite offers a peaceful retreat with access to a private en-suite bathroom. One guest bedroom even features a telescope, allowing guests to enjoy harbor views and stargazing from the comfort of the home. Additional amenities include: Central air conditioning Commercial-grade high-speed WiFi Washer and dryer Sonos whole-home audio system Backup generator Smart TVs throughout the home Whether you’re exploring the waterfront, setting sail on the harbor, enjoying fresh Maine seafood, or simply relaxing while watching boats pass by, Captain’s Quarters offers an unforgettable Boothbay Harbor experience. Things to Know This vacation rental is accessed by two steep flights of stairs and may not be suitable for guests with mobility limitations. The outdoor gas grill and patio area are shared with neighboring guests. Convenient walking access to downtown Boothbay Harbor, waterfront attractions, dining, shopping, and excursion departures.

You’ll be able to walk to the beach at Barrett Park, the footbridge, and the very heart of downtown Boothbay Harbor from this polished, dog-friendly home. Whether you choose to spend your days kayaking, whale-watching, or hiking, you’ll find that you’re just where you want to be. This family home is spread out across two levels, with hardwood floors and free WiFi throughout. As you enter, you’ll be greeted by a billiard room to the left and a living room to the right, where you can pile on the leather sofas, watch Netflix on TV, and play board games well into the evening. The light-filled, well-equipped kitchen is just beyond, offering stainless steel appliances, an eat-in dining table, and sliding doors that lead outside to the new composite deck, firepit, and gas grill. After a barbecue dinner and a walk around the neighborhood with your dogs, you can come home to toss the day’s clothes in the washer/dryer. There’s one bedroom on the main floor and two bedrooms upstairs - including a special room for the kids with chalkboards on the wall. Additional perks include ample parking. Things to Know Please note that dogs must be leashed and cleaned up after; there are foxes in the area. Dogs are not allowed to sleep on beds, but a dog bed is provided.

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.

You’ll be wonderfully located near the best of Boothbay Harbor at this home just across the footbridge from downtown. Enjoy fantastic access to Barrett Park and the Boothbay Lobster Wharf mere steps away. This home makes an enviable home base in Boothbay Harbor, whether planning to spend your days whale-watching, kayaking with Tidal Transit Kayak, or simply perusing the shops, restaurants, and galleries that populate this darling Midcoast town. After a day of coastal excursions, you’ll return to a casual, comfortable living area with two sofas and a smart TV, a well-appointed kitchen with all the essentials, and a small indoor dining space. Right out back are a small deck with outdoor seating and marshland views, a gas grill for summer barbecues, and a picnic table where you can gather for lobster rolls and haddock pulled straight from the ocean. There are cornhole and croquet games available for use as well! THINGS TO KNOW This home is the ground level of a duplex.

Cove Views | Breakfast Nook | WFH Friendly | Ground-Floor Unit | 4 Mi to Coastal Maine Botanical Gardens A serene coastal retreat awaits at this Boothbay Harbor vacation rental! With a picturesque waterfront setting and a prime location just a short walk from downtown shops and eateries, this 2-bedroom, 2-bath condo is perfect for a seaside stay. Embark on a sailboat tour, visit Coastal Maine Botanical Gardens, or check out Barrett's Park before returning home to relax on the furnished patio. -- THE PROPERTY -- SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 2 twin beds - Additional Sleeping: 1 queen air mattress INDOOR LIVING - Smart TVs w/ cable, gas fireplace - Laptop-friendly desk w/ printer - Breakfast nook, dining table - En-suite bathroom, walk-in showers OUTDOOR LIVING - Furnished patio w/ cove view, electric grill - Spacious yard KITCHEN - Refrigerator, stove/oven, microwave, dishwasher - Drip coffee maker, toaster - Dishware & flatware, cooking basics, spices GENERAL - Keyless entry, self check-in, free WiFi, central heating - Washer & dryer, laundry detergent, iron/board, trash bags/paper towels - Towels/linens, complimentary toiletries, shampoo/conditioner, hair dryer FAQ - No A/C - 2 exterior security cameras (facing out) ACCESSIBILITY - Single-story condo, step-free entry - 2 interior steps required to access living room PARKING - Designated parking spots (2 vehicles) - Overflow lot -- THE LOCATION -- - Walking distance to downtown dining & shopping, boat tours, Hodgdon Marina - 3 miles to Maine State Aquarium - 4 miles to Coastal Maine Botanical Gardens - 2 miles to Barrett's Park - 60 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 - While this single-story condo offers step-free entry, 2 interior steps are required to access the living room - The designated parking spots are not adjacent to the unit. Guests must travel across the parking lot to access the condo - This property does not offer air conditioning - Your safety matters. The property features 2 Ring security cameras located at the front and back doors facing outward. The cameras do not look into any interior spaces. The cameras record video and sound when motion is detected