We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

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.

0 of 0 items showing

1 of 3 pages

Farm stay in Alton

4.99 out of 5 average rating, 366 reviews

Treehouse Penthouse ❤ Beautiful inside & out

Kick back and relax in this calm, stylish apartment space. This space is an open concept with a king size bed. Lots of windows bring in natural light, cathedral ceiling and amazing view! A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have your own space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

Home in Freedom

4.98 out of 5 average rating, 104 reviews

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.

Guest suite in Wolfeboro

4.86 out of 5 average rating, 131 reviews

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!

Cottage in Freedom

4.79 out of 5 average rating, 455 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.

Rental unit in Porter

4.86 out of 5 average rating, 360 reviews

The Carriage House Apartment

A unique and inviting second floor apartment. Located in what was originally a carriage repair shop. Renovated into living space, the apartment offers a comfortable living room with high ceilings and exposed beams. A well equipped kitchen area, bedroom with two double beds and full bathroom. Our beautiful area offers a variety of activities including a scenic town beach a short walk down the road, hiking trails for all level, antique shops, great restaurants, seasonal fairs, and orchards.

Cabin in Tamworth

4.9 out of 5 average rating, 484 reviews

Luxurious Mountainside Cabin! Fantastic Views!

Cozy Cabin with Sweeping Mountain Views! A great escape with total privacy. Relax by the Giant Fire Pit overlooking the Mountains! Head up to North Conway to the White Mountains or go South to the Lakes Region. Then escape the traffic and retreat to the quiet of your Mountainside Cabin. Wood Fired Sauna on the premises! We provide everything you will need for your stay, and I mean everything, just bring a sense of adventure! Pets ok! *Pet Fee Applies! *Additional Fee for Sauna

Home in Albany

4.82 out of 5 average rating, 423 reviews

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!

Chalet in Freedom

4.93 out of 5 average rating, 194 reviews

Cute cottage with lake access at beach club.

My entire house just waiting to be enjoyed! A great get away for relaxing. King Pine ski hill is close by for winter fun. Summertime, I am a member of the Lake Ossipee Village Beach Club on Broad Bay, the most sandy beach with facilities. Enjoy the beach! Nearby, Freedom Town Forest trails await hiking/biking or Goodhue Boat Co. has boat rentals. If shopping is a must, Conway is 20 minutes north as are other ski hills. Antique/resale shops are nearby. Guests love the updated décor.

Home in Wakefield

4.93 out of 5 average rating, 105 reviews

Spacious Belleau Lake House Amongst the Trees

You and your family & friends will feel right at home in this spacious custom built home in the tall trees across the street from beautiful Belleau Lake. There are three levels of living space, making it a great destination for small or mid sized groups or families looking to share a vacation without compromising privacy. It is also perfectly cozy for a couple. Enjoy the peacefulness of being high amongst the trees with the glow of the lake and shared sandy beach just steps away.

Cottage in Brownfield

5 out of 5 average rating, 234 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.

Rental unit in Tamworth

4.89 out of 5 average rating, 158 reviews

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.

Guesthouse in Brownfield

4.87 out of 5 average rating, 430 reviews

Mountain Treehouse Guesthouse

Spacious 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Popular amenities for Ossipee vacation rentals

Free parking on premises

Air conditioning

Stay near Ossipee's top sights

Hobbs Tavern & Brewing Company68 locals recommend

White Lake State Park34 locals recommend

Yankee Smokehouse26 locals recommend

Pizza Barn20 locals recommend

Rosie's Restaurant19 locals recommend

Jake's Seafood and Grill18 locals recommend

Other great vacation rentals in Ossipee

Home in Wakefield

5 out of 5 average rating, 27 reviews

Modern Lakefront Cabin (Pet Friendly, King Beds)

Home in Freedom

5 out of 5 average rating, 19 reviews

Cozy 3-bdrm - Ossipee Lake access, Ski, Shop, Hike

Home in Ossipee

5 out of 5 average rating, 7 reviews

Cozy Lake & Mountain Stay in NH Lake Region

Home in Freedom

4.83 out of 5 average rating, 71 reviews

Cozy camp for swimming, water sports and more!

Home in Ossipee

4.89 out of 5 average rating, 53 reviews

Spacious, updated 2-bedroom home on golf course!

Cottage in Ossipee

5 out of 5 average rating, 5 reviews

Lakefront Cottage!

Home in Freedom

4.9 out of 5 average rating, 87 reviews

Our Mountain Retreat – Lake Ossipee Access

Rental unit in Wolfeboro

4.87 out of 5 average rating, 55 reviews

Surrounded by Recreation (2)

Quick stats about vacation rentals in Ossipee

Total rentals
150 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
5.5K reviews
Family-friendly rentals
120 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
60 properties have a dedicated workspace

Frequently Asked Questions

How much does it cost to stay in cabin rentals in Ossipee?
Experience the best of Ossipee with our cabin rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Ossipee?
Yes! Work meets play with ease at over 60 vacation rentals in Ossipee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Ossipee?
Ossipee has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do chalet rentals in Ossipee have wifi?
Absolutely! We offer over 10 chalet rentals with wifi in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Ossipee?
Make yourself at home in Ossipee by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Effingham Falls, and over 60 vacation rentals in West Ossipee.
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.
Are there pet-friendly vacation rentals in Ossipee?
Four-legged friends are welcome in Ossipee. Choose from more than 50 vacation rentals for guests traveling with pets.
What are the most popular amenities for Cabin Rentals in Ossipee?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 20 homes with a bbq area, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore