Cottage vacation rentals in Ossipee

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Ossipee

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

0 of 0 items showing

1 of 3 pages

Guest favorite

A person swims in clear water with a boat bobbing gently in the foreground. Lush green trees and charming cottages are visible along the shoreline under a bright blue sky dotted with a few white clouds.

Cottage in Northwood

4.91 out of 5 average rating, 252 reviews

Cottage near lake! Kayaks & canoe! Dog friendly!

Come relax, sit by the fire pit, walk the dirt roads & trials! Walk 2 min. to the boat launch/swim area & enjoy the canoe. WIFI. 500 mbps. Yard: grill out, make s'mores by the fire pit, play horse shoes. Inside: play games, complete puzzles, cuddle up and watch movies. Outings: Antique Alley, Chucksters, Stonehouse Pond, Meadows State Park, Portsmouth,Concord. *Sleeps 4. *PET FEE $25 per dog/ night. 1-2 behaved dogs. Dogs only due to health concern for cleaner. *Wear life jackets provided.

Superhost

Cottage in York

4.77 out of 5 average rating, 290 reviews

Sweet cottage in quiet convenient coastal setting.

Our winters are beautiful. Quiet and relaxing with many winter sports including snoeshoeing on Marginal way and many natural ice scating ponds. ride to Cape Neddick Beach, and minutes away from three other lovely beaches Relax in our private, romantic Cape Neddick cottage, overlooking a 2 acre meadow and woodland, close by foot, bike, to the amenities of York, Ogunquit, Kennebunk, Kittery, and Portsmouth. Our cottage is off the beaten path on a quiet private way, near the Cape Neddick River.

Superhost

A cozy fire pit area is surrounded by several white Adirondack chairs and black wire stools. Warm light strings hang overhead, creating a relaxed atmosphere. In the background, a pond is visible with a kayak on the shore and trees providing natural privacy.

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

Cottage in Whitefield

4.96 out of 5 average rating, 238 reviews

Private Pond Escape: Luxe Cottage/Private Isle

Luxurious Cottage on pristine private pond with outdoor wood fireplace and gas fire table. Cross graceful bridges to your Private Island with screened gazebo. Perfect getaway! Have coffee or cocktails on the deck with mountain and lake view or hike the trails on our 68 acres to the Gold Mine Trail. With a full kitchen, fine china, new shower, Jacuzzi bathtub, electric fireplaces, and two workspaces, this dog-friendly luxury cottage has it all! Make memories in this charming retreat!

Guest favorite

The image captures a tranquil scene of Mirror Lake, with gentle ripples reflecting the clouds above. A wooden dock extends into the water, providing a serene spot for relaxation. Lush greenery surrounds the shoreline, with distant mountains creating a peaceful backdrop.

Cottage in Whitefield

4.92 out of 5 average rating, 104 reviews

Cozy Lake Cottage; Bretton Woods & Santa's Village

Welcome to Selma Cottage, your lakeside haven among the picturesque White Mountains! Nestled on a charming shared property w/ direct access to Mirror Lake, we offer a serene escape in a standalone 450 sqft, one-bedroom oasis. Immerse yourself in lakefront living and explore the North Country. A year-round retreat, Selma is the perfect home base for laidback summer fun, stunning fall foliage, and snowy winter adventures. Swim, fish, kayak, hike, ski, explore, and above all relax at Selma!

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.

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 charming cottage is nestled among tall trees, framed by a peaceful natural setting. A spacious wrap-around porch is visible, providing shaded outdoor seating to enjoy 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!

Top 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