
Holiday rentals in Ossipee
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Top-rated holiday rentals in Ossipee
Guests agree: these stays are highly rated for location, cleanliness and more.

Romantic Mountain Cabin • Private Finnish Sauna
This romantic mountain cottage is one of the most-loved properties in the area — guests keep coming back to find out why. Cozy, private, and beautifully appointed, it sits above Tamworth with calming mountain views and complete quiet. Perfect for a couple's getaway, a remote work week, or just unplugging from it all completely. Step onto the deck with your morning coffee, then end your evening in the optional wood-fired Finnish sauna just steps from your door. Sauna available for a one-time fee.

Aspen Cottage - Charming Cottage with Beach Access
Nestled in the trees, at the end of a quiet road, you’ll find your next restful getaway. Central location perfect for relaxing or adventuring. Less than a 10 minute walk to multiple points of beach access or sunset viewing at Lower Beech Pond, a 155-acre lake within the Ossipee Mountain range, known for its excellent water quality and recreation. A 15 minute drive to downtown Wolfeboro and Lake Winnipesaukee. In the winter months, find miles of snowmobiling through NH's extensive trail system.

Perfect NH Getaway Retreat in the White Mountains
Perfect getaway for any season! Ideal location in the heart of NH White Mountains & Lakes Region. The beauty of this NH getaway is that while you’re only a few miles from numerous winter and summer recreational activities, restaurants and shopping; our home and neighborhood are a quiet retreat from the hustle and bustle. Meticulously cared for and decorated with country charm, our home has a modern kitchen, large master bedroom, and best of all, your own re-created English pub for entertaining.

Cozy Cabin Retreat just off Lake Ossipee
Nestled on 17 acres and backed by 400 acres of Ossipee Forest just off Lake Ossipee, this cabin is perfect for a quiet retreat or a home base for all the splendor NH has to offer. Sit by the fire with your favorite book and beverage or cook your favorite meal in the full kitchen. The wrap around screened in porch is a great place to enjoy company or stare off into the woods looking for wildlife to wander by. No matter the season this cabin is close to all your favorite outdoor activities.

Peaceful getaway with King Bed near Town
Welcome to the perfect Wolfeboro Getaway! King size memory foam mattress for a rejuvenating nights sleep. You will love the peace and quiet of this location with easy walkable access to everything in downtown Wolfeboro, Back Bay, and the waterfront. For nature lovers, there's hiking trails right at the end of the street, just take a left out the front door. Please note: There is a kitchenette with sink, refrigerator, coffee maker, toaster oven, and plug in cook top but no actual stove.

In the Trees - NH w/ Lake Access
RELAX in this BRAND NEW getaway with all the necessities to escape reality! Nestled on a hill within the trees, unwind with a beverage on the back deck or lower lounge and relish the peace and tranquility the property offers. Steps away from the beautiful Province Lake, take a swim or launch your boat for a cruise. Enjoy a scenic round of golf at Province Lake Golf Course & then enjoy a meal at the local restaurants or take a drive to explore Wolfboro (30mins) or North Conway (45mins).

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.

Peaceful Summertime Retreat: Private Horse Farm
Gorgeous foliage views from the big bay window. A nice 1 mile walking trail. A full kitchen to make homemade meals. A large TV to settle in and relax. A workspace if needed. Laundry. Extra space could be used for storage/air mattress/kid space. Come experience farm life and let us know if you want a visit with any of the animals. Horses, chickens & dogs. Our place is a perfect getaway for a couple or small family. Escape the busy city noise. Relax at our firepit and check out the stars

Cedar Hideaway: Walk to Pond, 15m N. Conway
Sip coffee on the screened porch listening to the wind in the pine grove. This modern cedar cabin is your sanctuary from the summer crowds, yet only 15 mins to the bustle of North Conway. Walk to the pond for a dip or read a book in the hammock. Equipped with fast WiFi and a fully stocked kitchen and charcoal grill. Cathedral Ledge and many hikes a short drive away. A tranquil, shady escape for those looking to slow down and breathe or your launchpad for White Mountain adventures.

Luxury Glamping NH - Geodome Sanctuary
Escape to a private luxury sanctuary retreat tucked behind a charming Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 90 minutes from Boston, yet a world away.

Kirkland Cottage (A ski and lake escape)
Welcome to Kirkland Cottage - great base for all New Hampshire has to offer! We’re a two minute drive from Ossipee Lake and right near the White Mountains, so you can explore lakes, mountains, and hiking trails. We are only an hour from Portland and Portsmouth. Kirkland Cottage house is 9 minutes to King Pine Ski area, 30 minutes to Cranmore, and 25 minutes to North Conway, which has great shopping, skiing, hiking, and lots of restaurants.

Ossipee Lake Waterfront Condo
Large, open, and bright. My condo on Lake Ossipee has four levels of relaxing living space, including beds to sleep 6 (max allowed per new Ossipee permit rules). One king, one Queen and two pairs of Twins in four bedrooms. Open plan, comfortable living room and den along with granite in the kitchen, new hardwood floors and tile throughout. 3.5 baths including a master bath, make this house very comfortable for large families and groups
Popular amenities for Ossipee holiday rentals
Other great holiday rentals in Ossipee

Waterfront cottage on Bearcamp River in OssipeeNH

Cozy Cabin w/ Pond Access - Kayak, Hike, Shop, BBQ

Sweet Apple Camp at Grey Shingles Camps

Beautiful & Relaxing Retreat Close to Ossipee Lake

The Ossipee Overlook | Spacious and Stunning Views

Nordic Cabin - Hot tub/Sauna/fire pit/waterfront

Heaven on the Water

Peaceful Ossipee Lake Cottage Private Beach/Dock
When is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $294 SGD | $343 SGD | $365 SGD | $290 SGD | $290 SGD | $308 SGD | $314 SGD | $340 SGD | $290 SGD | $307 SGD | $307 SGD | $309 SGD |
| 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Ossipee?
Ossipee has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in tiny house rentals in Ossipee?
Experience the best of Ossipee with our tiny house rentals, starting at about $9,990 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Ossipee?
Four-legged friends are welcome in Ossipee. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Ossipee?
Yes! Work meets play with ease at over 50 vacation rentals in Ossipee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Ossipee vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Ossipee, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Ossipee?
Make yourself at home in Ossipee by choosing from our most frequently booked neighborhoods. We have over 80 vacation rentals in West Ossipee, and over 70 vacation rentals in Effingham Falls.
Do cottage rentals in Ossipee have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ossipee have a kitchen?
Absolutely! We offer over 80 house rentals with a kitchen in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Do tiny house rentals in Ossipee have wifi?
Absolutely! We offer over 10 tiny house rentals with wifi in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Ossipee have free parking?
Absolutely! We offer over 80 house rentals with free parking in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Ossipee

Total holiday rentals
Explore 160 holiday rentals in Ossipee

Nightly prices starting at
Ossipee holiday rentals start at $52 SGD per night before taxes and fees

Verified guest reviews
Over 5,600 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
150 of Ossipee holiday rentals include wifi access

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

4.9 Average rating
Ossipee stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Pet-friendly rentals Ossipee
- Rentals with a washing machine and dryer Ossipee
- Rentals with lake access Ossipee
- Rentals with a kayak Ossipee
- Waterfront rentals Ossipee
- Family-friendly rentals Ossipee
- House rentals Ossipee
- Beachfront rentals Ossipee
- Rentals with outdoor seating Ossipee
- Rentals with a fireplace Ossipee
- Rentals with a patio Ossipee
- Rentals with a firepit Ossipee
- Cottage rentals Ossipee
- Sebago Lake
- White Mountain National Forest
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Loon Mountain Resort
- Pats Peak Ski Area
- York Harbor Beach
- Willard Beach
- Scarborough Beach
- Short Sands Beach
- Mount Washington Cog Railway
- East End Beach
- Footbridge Beach
- Cranmore Mountain Resort
- Tenney Mountain Resort
- Cape Neddick Beach
- Franconia Notch State Park
- Gooch's Beach
- Omni Mount Washington Resort
- King Pine Ski Area





