
Vacation rentals in Ossipee
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Ossipee
Guests agree: these stays are highly rated for location, cleanliness, and more.

Rustic Rose Cottage of Historic West Lebanon
Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

Perfect Family Getaway On Lake Ossipee
Our 10 year old home has four bedrooms three baths, theater room, gas fireplace, bar outdoor fire pit, open concept kitchen, nestled in a mountain landscape. Beautiful private beach with a playground, picnic area and boat launch only a short walk away. Tennis courts and a basketball court centrally located within the community. Boat rentals available on the lake. Multiple ski areas close by. Easy access to local and state snowmobile trails and the lake for ice fishing right out of the driveway.

Rustic Mountainside Chalet
Located on a wooded mountainside in the White Mountains & the Lakes Region of NH, close to hiking, 5 minutes to the rivers and 15 minutes to Lake Chocorua and Lake Ossipee for swimming/kayaking/tubing or just relax and enjoy the views of the mountains. Peaceful Chalet with one bedroom with one bunk bed unit with queen mattresses, and a large master bedroom loft with Cali King, kitchen, and 2 x bathrooms, a deep jetted tub. The basement is converted into an in-law’s suite where my parents live.

Mountainside Retreat! Great Views! Cozy & Private!
Romantic Mountainside Cottage! A Cozy Escape with Wonderful Views of the Mountains. Very Private, Romantic & Luxurious stay in the Woods of NH. Fire Pit overlooking the mountains! Visit the town of Tamworth, head up to North Conway White Mountain's, or head south to the Lakes Region. All less than an hour away, then escape the traffic and retreat to the remote and quiet of your Mountain Cottage. We provide everything you will need for your stay, just bring a sense of adventure! Pets Yes!

Downtown, Cozy, Cute, and Convenient!
Walk just one block to the heart of downtown Wolfeboro, the "Oldest Summer Resort in America". Dine, shop, visit art galleries, or just relax in the park overlooking the docks on Wolfeboro Bay. Take the Mt Washington Ferry for a Lake Winnipesaukee ride or Molly the Trolley hop on/off tour. The rail trail is close by and a playground is just steps away for the little ones. Also, Wolfeboro’s best Mexican restaurant, coffee shops, Hunter’s grocery and Walgreens are all just a short walk away!

Cozy Guest Suite in White Mountain National Forest
Guest Suite, mother-in-law apartment with private entrance. One bedroom with living room, dining area, kitchen, stove, full refrigerator. WiFi and a futon couch that turns into a bed in the living room. The converted basement apartment is a comfortable, and cozy place to stay while visiting the Mount Washington Valley. Perfect for adventuring, climbers, hikers, bikers and skier/snowboarders. Have a hot pot of organic local coffee and get outside in the beautiful Mount Washington Valley!

Clean, quaint studio apartment on small farm
Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

1BR cozy, luxurious getaway @ Krista's Guesthouse
Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Mountain Treehouse Guesthouse
Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

The Village House
Welcome to our recently renovated home , built in the late 1890's in the heart of beautiful Tamworth Village, right on quiet Main st. A quick 5 minute walk to "downtown", Remick Farm and museum, Barnstormers summer theatre and The Other Bakery. Tamworth is home to many local hiking trails from easy walks to over 4000 foot summits. Great place in the winter with miles of free , groomed cross-country skiing and snowshoeing trails as well.

CloverCroft - "Far from the madding crowd."
CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Cozy camp for swimming, water sports and more!
Our lake house is nestled into the woods with direct access to Ossipee lake. “The Pancake House” combines the best of a campy camp with modern amenities. The mountain view from the lake is stunning! Our game room, lakefront recreation options and two additional living rooms will keep everyone relaxed and entertained with plenty of space to relax and unwind. We are centrally located to many outdoor activities.
Popular amenities for Ossipee vacation rentals
Other great vacation rentals in Ossipee

Lakefront Oasis Priv Beach Swim Kayak Fish FirePit

Waterfront cottage on Bearcamp River in OssipeeNH

Peaceful Autumn Retreat: Private Horse Farm

Cozy Cabin Retreat just off Lake Ossipee

The Ossipee Overlook | Spacious and Stunning Views

3 bdrm + game room - Lake, Ski, Hike, Shop!

The Tinker Bell on Ossipee Lake

Spacious, renovated 2-bedroom home on golf course!
When is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $316 CAD | $319 CAD | $315 CAD | $316 CAD | $316 CAD | $336 CAD | $343 CAD | $371 CAD | $316 CAD | $290 CAD | $291 CAD | $316 CAD |
| Avg. temp | -5 °C | -3 °C | 1 °C | 7 °C | 13 °C | 18 °C | 21 °C | 20 °C | 16 °C | 10 °C | 4 °C | -1 °C |
Quick stats about vacation rentals in Ossipee

Total vacation rentals
Explore 160 vacation rentals in Ossipee

Nightly prices starting at
Ossipee vacation rentals start at $56 CAD per night before taxes and fees

Verified guest reviews
Over 5,500 verified reviews to help you choose

Family-friendly vacation rentals
120 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
150 of Ossipee vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Ossipee rentals

4.8 Average rating
Ossipee stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Mount Pocono Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Jersey City Vacation rentals
- Island of Montreal Vacation rentals
- Rentals with lake access Ossipee
- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Rentals with a fireplace Ossipee
- Rentals with a patio Ossipee
- Beachfront rentals Ossipee
- Rentals with outdoor seating Ossipee
- Rentals with a washer and dryer Ossipee
- Rentals with a kayak Ossipee
- Rentals with a firepit Ossipee
- Pet-friendly rentals Ossipee
- Waterfront rentals Ossipee
- Family-friendly rentals Ossipee
- House rentals Ossipee
- Cottage rentals Ossipee
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Squam Lake
- Story Land
- Scarborough Beach
- York Harbor Beach
- Weirs Beach
- Attitash Mountain Resort
- Long Sands Beach
- Loon Mountain Resort
- Mount Washington Cog Railway
- Franconia Notch State Park
- Pats Peak Ski Area
- Diana's Baths
- East End Beach
- Dunegrass Golf Club
- Omni Mount Washington Resort
- Funtown Splashtown USA
- Tenney Mountain Resort
- Willard Beach
- Cannon Mountain Ski Resort
- Parsons Beach
- King Pine Ski Area