Cottage vacation rentals in Ossipee

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Top-rated cottage rentals in Ossipee

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Guest favorite

Cottage in Whitefield

4.96 out of 5 average rating, 214 reviews

Sunny Waterfront Cottage on Private Lake

Waterfront! Steps to your own dock on private lake. Relax in your private screened pavilion with fire table and enjoy this bright, wood lined cottage with all you need for a spectacular getaway-Japanese soaking tub, (small) Heat/AC, +fast wifi. Cook in the well supplied kitchen or grill in the beach side pavilion. Walk the trails around the lake or to the adjacent 300 acre forest. This DOG FRIENDLY cottage has 68 acres of forest, meadow and trails. Private lake shared by only 2 other cottages

Superhost

Cottage in Freedom

4.79 out of 5 average rating, 483 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Lakefront House, contemporary, amazing views, large deck, private lake beach & dock, steps from house (swimming). Very fast internet, multiple users. Private free parking. Fully equipped kitchen, AC, Smart TV & Modern shower room. Laundry Equipment, all Linen supplied. Sun trap West Facing Deck with loungers for relaxation. Canoe, life preservers & paddles included. 2 Fire pits & Grill. Boat put-in locally. Following cleaning codes: Airbnb & other authorities. Please ask any questions.

Top guest favorite

A partially finished game room features a pool table centered under soft twinkling lights. The wooden table is set up with a cue ball and the colorful triangle of balls ready for play. A small bar area with two stools is visible against the wall.

Cottage in Conway

4.96 out of 5 average rating, 117 reviews

Cozy Cottage close to town and area attractions

Welcome to our family cottage located minutes from everything the valley has to offer! Skiing, riding, hiking, swimming, shopping and everything we love about the North Conway area only a short ride away. Well appointed home offering all you will need on your getaway no matter the season. Snuggle up on the over-sized leather furniture while watching a movie or reading a book. Watch the sunrise off the large deck while enjoying your coffee. Smart TVs and games to keep all entertained!

Top guest favorite

A hammock is suspended between two trees by the lake, inviting relaxation by the water. Two simple adirondack chairs sit on the sandy ground, offering a place to enjoy the serene view. A canoe is positioned nearby on the shore, surrounded by a natural landscape.

Cottage in Middleton

4.97 out of 5 average rating, 152 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.

Superhost

A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.

Cottage in Parsonsfield

4.87 out of 5 average rating, 158 reviews

Riverpine Retreat - clean&bright waterfront home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Guest favorite

Cottage in Wolfeboro

4.95 out of 5 average rating, 110 reviews

Lake Winnie Cozy Cottage Getaway

Welcome to Lake a Dream… Here is your chance for a fun filled family vaca on Lake Winnie in the summer or a cozy couples getaway in the winter! With just a quick 3 minute walk you can enjoy some sunshine & sand on the beach! Or a 5 minute drive into downtown Wolfeboro to experience it’s charm; waterfront dining, ice cream, shops, cafés & more! For winter stays, cozy up by the fireplace with a cup of hot cocoa & some fun family games! The cottage is not far from Gunstock & Kingpine.

Guest favorite

A vase filled with pink tulips sits on a rustic wooden table. Natural light pours in through a window, highlighting the fresh blooms and the texture of the table. The backdrop features soft, muted colors from the cottage's interior.

Cottage in Buxton

4.97 out of 5 average rating, 145 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

A vibrant sunset reflects on the calm lake water, showcasing hues of pink, orange, and purple across the sky. Silhouettes of trees line the shore, and gentle ripples can be seen on the surface, creating a serene atmosphere as day transitions to night.

Cottage in Alton

4.99 out of 5 average rating, 104 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

Top guest favorite

A gentle green landscape is viewed from two white Adirondack chairs positioned on the grass. A wooden fence runs through the scene, surrounded by trees that provide ample foliage. The sky is clear and bright, enhancing the tranquil setting.

Cottage in Brownfield

4.99 out of 5 average rating, 250 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Top guest favorite

The exterior of the Carriage House is highlighted by rustic wooden siding and a welcoming entrance. A fire pit is surrounded by seating, creating a cozy outdoor gathering space. Lush greenery frames the area, contributing to a serene atmosphere.

Cottage in Tamworth

4.92 out of 5 average rating, 179 reviews

*Amazing Reviews! *Outdoor Shower -TINY Cottage!

This guesthouse located in the beautiful & historic Tamworth/Chocorua New Hampshire. This house has many special areas to just relax & enjoy nature and the peacefulness this area of the world has to offer! Travel inspired & colorful! You will love both the front and back patios one with a grill & gazebo for outdoor dining in any weather & nicely lit at night & the other with a great porch and fire pit area. The outdoor shower off the porch is just AMAZING!

Guest favorite

Cottage in Middleton

4.96 out of 5 average rating, 188 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Guest favorite

A bright sleeping area features a spacious bed with light-colored bedding and decorative pillows. Large windows allow natural light to flood the room, framing a view of the lake and surrounding trees. The cozy ambiance is complemented by wooden beams overhead.

Cottage in Conway

4.96 out of 5 average rating, 153 reviews

Tiny Lakefront Cottage

This cottage was completely redesigned to better utilize space and maximize comfort. This home sits on beautiful Pequawket Pond in the White Mountains of New Hampshire. Just a few steps away from the water, this studio is one of 7 cottages in a private homeowners association. Guests are able to use our kayak and 2 paddle boards to explore or, enjoy our brand new patio and grill while taking in the gorgeous views.