Cottage vacation rentals in Ossipee

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Top-rated cottage rentals in Ossipee

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Guest favorite

A shaded outdoor deck features a comfortable seating area with plush cushions, overlooking a tranquil lake. Sunlight reflects off the water, and trees create a natural border, providing privacy. A kayak can be seen at the water's edge, enhancing the outdoor experience.

Cottage in Sumner

4.95 out of 5 average rating, 19 reviews

Peace at the Pond with Hot Tub & Sauna

Relax with the whole family at this dog-friendly, private cottage with all the amenities and easy access to nearby trails, restaurants, and movies within 1/2 hour. It's a waterfront paradise with hot tub, fully restored Finnish sauna, kayaks and canoe. Or just relax in the hammock with a book, after an outdoor (or indoor) shower. Spend the day swimming and canoeing, read a book on the shaded deck, and grill your dinner outside. Or satisfy your entertainment habits by streaming Netflix or PRIME!

Superhost

A sunlit sunroom features large windows inviting natural light, overlooking the wooded surroundings. A cozy sectional sofa is complemented by a round coffee table and woven area rug. A decorative chandelier hangs above, and a wooden dresser adds modern charm to the space.

Cottage in Lyman

4.82 out of 5 average rating, 101 reviews

RK North : All season Waterfront cottage with dock

Waterfront get away !You will love the cottage in any season - right on the pond! Enjoy a private dock, swimming and floating right at your door. Relax at the fireplace under twinkle lights , enjoy birdwatching, hiking and swimming during your stay. Lots of ATV and snowmobile trails near by. A close drive to Kennebunkport where your find beach’s , shops and restaurants galore. The cottage has 2 kayaks and a canoe for use during your stay. There are 2 Smart TVs for streaming. Shows and DVD

Guest favorite

A bright living area features a spacious sectional sofa adorned with colorful cushions. A granite countertop with woven bar stools offers a casual dining option, while natural light pours in through large windows adjacent to a screened-in dining space.

Cottage in Wells

4.94 out of 5 average rating, 147 reviews

Cozy Cottage with Ocean Views, Wells Maine

Ocean breezes, panoramic views of the Atlantic, comfortable cottage to relax & enjoy your time in Maine, what more could you ask for on a getaway?! This cozy cottage for 6 boasts near panoramic views of the Rachel Carlson preserve and the Atlantic Ocean. Tastefully decorated and newly updated, our cottage offers AC/heat, ceiling fans, fully equipped kitchen with dishwasher, outdoor gas grill, cable TV in all rooms, WiFi, cabled phone, skylights, in unit W/D & a large screened in porch.

Guest favorite

A wooden dock extends over the calm lake water, surrounded by lush greenery and rocks. The distant shoreline is outlined by trees under a cloudy sky, while a buoy can be seen floating in the water, adding a touch of color to the serene landscape.

Cottage in Raymond

4.91 out of 5 average rating, 110 reviews

Relax by a Quiet Lake

Charming lakeside cottage only 29' from the waterline, w/65' of private waterfront. The cottage is a 3-season, classic L.C. Andrews, log-sided Maine summer lake home. Cozy atmosphere and a wonderful enclosed porch with amazing waterfront views. Enjoy fishing off the dock, hiking, canoeing, camp fire, and exploring surrounding areas. Air conditioning units will ensure your comfort on warm summer nights and high-speed internet will keep your devices connected. Furnishings are family mix.

Superhost

A paddleboard floats on calm waters near the cottage, showcasing the exterior's gray siding and large screened-in porch. A person sits on the board with a dog standing beside them, surrounded by lush greenery and the peaceful cove.

Cottage in Kennebunkport

4.8 out of 5 average rating, 5 reviews

Waterfront Cottage on Paddy Creek

Private waterfront cottage with ocean, island and lighthouse views on quiet tidal cove. Located in Cape Porpoise, a small fishing village which is part of Kennebunkport. Fully equipped eat-in kitchen, screened-in porch, both overlooking the cove. Large living room with two twin built-in daybeds and fireplace, cozy master bedroom and bath. Pier and water access for kayak, canoe or boat owners. It is a scenic walk to the local pier, A short drive to the beaches and Kennebunkport center.

Top guest favorite

A serene lakeside view showcases calm waters reflecting the vibrant sky and surrounding trees. Wispy clouds stretch across the blue expanse, while shades of green from the forest create a peaceful atmosphere. The landscape is framed by rocks at the water's edge.

Cottage in Middleton

4.97 out of 5 average rating, 151 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Guest favorite

A wrap-around porch features a mix of seating, including a woven loveseat and two bright blue chairs. Warm lighting is provided by hanging bulbs above, and large windows offer unobstructed views of the surrounding landscape.

Cottage in Bridgton

4.91 out of 5 average rating, 180 reviews

True Maine Artist Cottage with Outdoor Shower

Featured on Huckberry!! Beautifully decorated seasonal artist cottage with brand new soaking tub and outdoor shower. Solo stove fire pit and Adirondack chairs. Huge wrap-around porch with outdoor seating and glorious sunset views across blueberry fields. Also amazing stargazing!! Close to Naples, Bridgton, Sebago Lake. Tons of lakes nearby, hiking, swimming, boating, restaurants, music and local beer! Great place to stay to explore the area or also just relax and hang out.

Top guest favorite

The secluded saltbox cottage is illuminated by warm outdoor lights, creating a welcoming ambiance. The exterior features large windows that reflect the evening glow. A cozy seating area with adirondack chairs is positioned on the lawn, surrounded by trees for added privacy.

Cottage in Thornton

4.95 out of 5 average rating, 153 reviews

Cottage with antique charm view & river HSI Wi-Fi

Immerse yourself in nature at our secluded saltbox cottage, where tranquility meets adventure. Explore nearby trails, ski slopes, and fishing spots. Inside, the cozy ambiance with a fireplace and a library of books invites you to unwind. Outside, the fire pit, hammock, and marked trails to the pond offer a true escape. With high-speed Wi-Fi, a desk, and a pet-friendly policy, your retreat is complete. Discover the perfect blend of comfort and nature for a memorable stay!

Guest favorite

Two wooden chairs are positioned across from each other on a grassy area, facing a small fire pit. Lush greenery surrounds the space, while trees are visible in the background under a clear blue sky.

Cottage in Buxton

4.98 out of 5 average rating, 142 reviews

Peaceful Cottage on Maine Flower Farm

Overlooking vibrant flower fields at Ferris Farm, this charming cottage offers a peaceful retreat to relax and reconnect with nature. Wake up to scenic views, sip coffee on the deck, and explore the farm before spending the afternoon kayaking the Saco River. Use the cottage as a home base to visit Old Orchard and Saco beaches or experience Portland’s craft breweries, coffee shops, and incredible dining. Ideal for a solo retreat, romantic escape, or remote work getaway.

Top guest favorite

Two Adirondack chairs are positioned on a wooden dock, overlooking a tranquil lake. The water reflects warm hues of orange and pink as the sun sets behind distant hills, creating a serene atmosphere. Soft grass borders the edge of the dock.

Cottage in Alton

4.99 out of 5 average rating, 102 reviews

Lake view cottage #2 in Alton Bay on Winnipesaukee

Cottage #174 is one of our 3 cottages. This cozy STUDIO cottage (225 SF ) has a queen size bed/den area , fully equipped kitchen and Full Bath. AC, Wi-Fi , TV with ROKU included. Cottage has its own outside space overlooking the lake with table and chairs making it the perfect setting to relax and enjoy the beautiful lake views. The entire area is fenced in. See other listings Lake view cottage #1 &3 in Alton Bay on Winnipesaukee SEE INFO BELOW ABOUT EXTRA BOAT SLIP

Guest favorite

A private outdoor deck features two wicker chairs with soft cushions, set against a backdrop of greenery. Natural light reflects off the white siding of the cottage, while views of the surrounding marshland can be glimpsed beyond the deck railing.

Cottage in Ogunquit

4.92 out of 5 average rating, 101 reviews

Cottage at Footbridge Beach Ogunquit

Our one bedroom cottage is a perfect spot to enjoy all the beach life has to offer! This charming cottage is just a few minute walk to the Footbridge and Ogunquit beach and close to many popular restaurants and bars. The bedroom has a queen size bed , tiled bathroom, cozy living area and a kitchenette with a refrigerator, microwave, toaster oven and coffee maker. Limited marsh views from the private outdoor space with room to grill and relax. All linens provided

Guest favorite

A vibrant tree showcases bright red leaves, contrasted by hints of green from adjacent foliage. The scene captures the essence of autumn with nature's colors creating a warm visual display along the roadside.

Cottage in Norway

4.92 out of 5 average rating, 137 reviews

Cottage with Whirlpool tub - McLeod

The town of Norway has recently been recognized in the top 3 coolest small Towns in Maine you may never have heard of. Hillside Cottages offers that special something that every vacation needs. If you’re looking for a friendly vacation destination which offers a truly relaxing getaway, then look no further. Close to the shores of Norway Lake in the Lakes and Highlands of Western Maine, Hillside Cottages are waiting for you.