Vacation rentals in Sheepscot Pond

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Top-rated vacation rentals in Sheepscot Pond

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Four brightly colored Adirondack chairs surround a stone fire pit, positioned on a grassy area facing a calm body of water. A scenic view of clouds reflecting on the water's surface enhances the tranquil atmosphere.

Home in Stockton Springs

4.91 out of 5 average rating, 77 reviews

Oceanfront Home Acadia-Camden -Belfast

Relax with the whole family at this peaceful place just one hour from Acadia National Park. Centrally located in Mid Coast Maine, this home is the perfect location to spend time by the salt water or take day trips to the surrounding attractions. Small private beach and 3 other public beaches nearby. Kayak right in front of the property or relax by the wood fire pit and look out onto the water. This home offers everything you will need to make for a great escape from the demands of daily life.

Guest favorite

Home in Boothbay

4.83 out of 5 average rating, 6 reviews

Tailwinds - Upscale Oceanfront! Stunning Views!

Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, this is a perfect place to gather frinds and family with en-suite baths 2 living rooms and a large porch. You will also find all new beds and furniture, luxurious 100% cotton linens, and AC window units in the bedrooms. Located between downtown Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

Guest favorite

A serene lakeside view is captured at sunset, showcasing the soft glow of the sun reflecting on the water. A wooden dining table with chairs is positioned on the deck, accompanied by a large umbrella, enhancing the inviting outdoor space.

Home in Liberty

4.98 out of 5 average rating, 47 reviews

Peaceful Lakeside Getaway with Hot Tub!

Enjoy our fully renovated, lakeside, four season retreat. During the summer spend time fishing, kayaking, swimming, lounging in the hammock and then escape the heat inside the fully air conditioned house! In any season, unwind in the lakeside hot tub, take in every gorgeous sunset and dark starry night or gather around the campfire. The winter months bring snow shoeing, ice fishing, snuggling up in the living room playing games or watching a movie fireside. There is something for everyone!

Guest favorite

A serene ocean view showcases a sailboat gliding across calm waters, framed by lush greenery and a rocky coastline. The expansive sky is filled with soft clouds, creating a tranquil atmosphere that invites relaxation and reflection.

Cottage in South Thomaston

4.95 out of 5 average rating, 104 reviews

Cottage by the sea private oceanfront shoreline

Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

Superhost

The exterior of a white home is surrounded by lush greenery and blooming flowers. Varieties of trees and shrubs provide a natural border, while the spacious lawn invites outdoor relaxation. Clear blue skies overhead enhance the serene setting.

Home in Deer Isle

4.97 out of 5 average rating, 30 reviews

Charming restored 1830s cape DeerIsle

Full of light with thoughtful touches throughout this sunny 200 year old home is perfect for your quintessential Maine getaway. Our carefully designed coastal retreat is central to many of the adventures in coastal Maine. 3 bedrooms including 1 king suite, 1 king bedroom, a double trundle room, a well stocked kitchen, bath, grill and fire pit. Perfect for family fun, couples' retreats, visits to Acadia National Park, and other activities for up to 8 guests. 3 minutes to Causeway Beach!

Top guest favorite

A wooden staircase leads upward, illuminated by natural light. A framed art piece hangs on the wall, and a potted plant is positioned on the landing. The railing features a curved design, complementing the warm wooden tones of the stairs.

Guesthouse in Belfast

4.98 out of 5 average rating, 51 reviews

Adorable cottage 5 minute walk from downtown

Newly custom renovated 1 BR, 2 floor cottage 5 minute walk from downtown, 2 minutes from farmers market & bay. Each floor has a balcony for AM coffee/evening drinks. Loft style master BR connecting bathroom, first floor kitchen/living room combo - full (compact) kitchen - Custom woodwork, great design. Bathroom accessible from 2nd Fl BR. (The couch was recently replaced it’s not the one pictured (it’s actually much more comfortable) Crib available upon request No pets No smoking

Top guest favorite

A charming cottage is framed by lush green trees, showcasing its light yellow exterior and welcoming front door. The grassy area surrounding the home offers a tranquil setting, and the clear sky above adds to the serene ambiance.

Guesthouse in Islesboro

4.96 out of 5 average rating, 24 reviews

Milk House

nice little vacation cottage in Dark Harbor, near to everything. queen sized bed, so sleeps up to two in a quiet island location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speeds are excellent, although I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, this property is on an island, which must be accessed by boat or ferry, so service can be interrupted.

Top guest favorite

A screened porch offers a view of Penobscot Bay, featuring two green wicker chairs adorned with floral cushions. The scenery includes a lush lawn and Adirondack chairs positioned for relaxation, with water visible in the background and distant hills framing the horizon.

Cottage in Belfast

4.99 out of 5 average rating, 122 reviews

Spectacular Cottage on Penobscot bay in Belfast

Spectacular cottage on Penobscot bay in Belfast. The cottage is focused on the views from the great room and screened porch. You’ll love the spacious, clean, open cottage with a complete kitchen and propane fireplace. Sit on the porch with a book/glass of wine and watch for seals and schooners. Easy access to the shore along a gradual path and short boardwalk. Great amenities and comfort for vacationers both young and old. Perfect for couples and families (with kids).

Top guest favorite

Two white Adirondack chairs are positioned near a stone fire pit, surrounded by lush greenery and autumnal foliage. Sunlight filters through the trees, creating a serene outdoor space for relaxation.

Home in Freeport

4.99 out of 5 average rating, 77 reviews

Freeport Escape – LLBean | Fire Pit | 3 King | A/C

The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82

Guest favorite

Home in Boothbay

4.98 out of 5 average rating, 51 reviews

Postcard views, ocean front and idyllic cove

Cozy and comfortable unique home nested on the granite ledge at the mouth of Little River and the open ocean in East Boothbay, Maine. Marvel in glorious views from every window, deck and porch. Soak in the salt water hot tub, light up the evening by the outdoor fireplace or just get lost in the starry night sky. Most of all, enjoy every moment and make lifetime memories!

Guest favorite

The view from the balcony displays trees framing the Sheepscot River. Nearby cottages with varying roof styles are visible alongside the water, with a pier extending into the distance. The sky is partly cloudy, adding depth to the serene landscape.

Townhouse in Edgecomb

4.92 out of 5 average rating, 142 reviews

Joyful Maine Escape: 3 Bdr. Waterview Townhouse

A spacious townhouse to vacation with 3 bedrooms and view of the Sheepscot River. This stylish, relaxing townhouse is perfect for family and friends looking for a Maine retreat. Relax by the fire pit on the patio or on the balcony overlooking the Sheepscot River after a day of kayaking, antiquing, or an evening in nearby Wiscasset. Pets Welcome! Self Check In/Out

Guest favorite

The image captures a serene coastal scene during sunset. Silhouetted figures sit on large rocks, overlooking calm water reflecting soft hues of orange and blue. A distant island is visible, framed by trees, creating a peaceful, natural setting.

Home in Stonington

4.79 out of 5 average rating, 110 reviews

Island Getaway - 4BR House (Ocean Views)

★ You will be walking distance from downtown Stonington where you can enjoy local shops, artwork and immerse yourself in the island community. A delightful in-town home with views of Stonington Harbor! The property has a large yard with minimal traffic, perfect for families or a friends getaway. ★ Complementary Kayaks Rentals when you stay 3 nights or more!

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What guests are saying

Rustic Home on Private Pond

4.93 out of 5 average rating, 60 reviews6 months ago

Perfect location for Acadia if you are looking to be in a rural location around a hour or so drive. Blue hill avoids the hustle and bustle of bar harbor. Daniel’s place has an extended back yard to a pond and the scenery is gorgeous. No issues at the home, everything was great and Daniel reached out several times to ensure all was well. Recommend to all.

Cabin in Blue Hill

What guests are saying

Oceanview Escape near Maine Beaches

4.93 out of 5 average rating, 90 reviews6 months ago

What a cozy, beautifully furnished and decorated space. A lot of thought went into making guests feel they’re staying somewhere very special. We certainly did. The second floor apartment with its spacious deck had a view of the ocean and some spectacular sunrises. This was our first visit to Maine and we wanted somewhere central on the coast, like Owl’s Head. It was a good base to explore from. And there was lots to do close by. We were especially pleased to discover the Bernard Langlais art preserve only a few miles away. Rockland is ten minutes away and has a lot of great places to eat.

Apartment in Owls Head

What guests are saying

The South Bay Maine House "on the rocks"

4.91 out of 5 average rating, 11 reviews8 months ago

Gorgeous, well appointed Airbnb. It was even better than expected. Our family very comfortable and enjoyed all aspects of this very pretty location. The house had fantastic amenities on top of being in an amazing setting. We’ve discussed how we could return….

Home in Penobscot

What guests are saying

Spruce Tops Cottage

4.95 out of 5 average rating, 84 reviews6 months ago

The cottage was cozy, clean and comfortable. Peaceful surroundings, can see the ocean and inlet with the lobster boats leaving and bringing in their catches, the location was perfect for day trips to other surrounding towns. We met Susan and her sweet dog, she was very nice and friendly, had suggestions of places to see , do and restaurants in the area. Overall it was a wonderful experience, would definitely recommend.

Cottage in Bristol

What guests are saying

Cozy, Comfortable, welcoming With private suite

4.8 out of 5 average rating, 15 reviews2 months ago

Marks place made our trip to visit family very comfortable and convenient to visit in the middle of winter. Very cozy and inviting and Mark was very attentive to ensuring our check-in and stay was great. If your looking for a great stay in Skowhegan with plenty of space and accommodation look no further.

Home in Skowhegan

What guests are saying

Ocean View Cottage with Three Porches in Boothbay

4.67 out of 5 average rating, 3 reviews46 months ago

Absolutely heavenly stay in this authentically Ocean Point home. My family has been visiting Ocean Point for 40 years now and this house is so recognizable to us: it is absolutely a centerpiece of the coastal landscape, and we felt overjoyed to be able to stay there. There’s plenty of space for a family to gather, uninterrupted views, and all the charm of objects gathered over the history of the home. Thank you to Wendy for being such an excellent hostess!

Cottage in Boothbay

What guests are saying

Island Getaway

5 out of 5 average rating, 30 reviews6 months ago

When we planned this vacation, we were looking for a location that provided serenity, a beautiful view, and walkable areas to totally relax from hectic year. Brad and Kathy's place far exceeded our expectations in every way. Their warmth, friendliness and helpfulness were felt throughout the week. Everything from attending yoga classes, golfing at North Haven and delicious fresh lobsters. It was a great experience and one that we certainly would re-visit in the future. Brad and Kathy are not just super hosts they are "super, super hosts!"

Home in Vinalhaven

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