Compare vacation rentals in Ossipee, NH from 100+ sites!

242 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Ossipee, NH vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Ossipee, NH

Search Vacation Rentals near the Old Town in Ossipee, NH

From vibrant downtown areas to historic streets, these Ossipee, NH vacation rentals put you close to everything worth seeing.

The Green Lake House, Wolfeboro, Nh - Ossipee, NH
9.9 19 reviews

The Green Lake House, Wolfeboro, Nh

apartment, Wolfeboro
This three-bedroom Wolfeboro lake house offers private Lower Beach Pond access for swimming and kayaking, and is within 30 miles of Gunstock Mountain, King Pine, and Abernaki ski areas.
The 3-bedroom home, comfortably sleeping six, features a fully equipped kitchen, a cozy living room, a bonus living room, an outdoor deck, and a full bathroom with laundry; guests can enjoy nearby dining and shopping in towns like North Conway, Laconia, and Meredith.
Lake Access 2br + Loft W/deck | Lower Beech Pond - Ossipee, NH
9.4 36 reviews

Lake Access 2br + Loft W/deck | Lower Beech Pond

apartment, Tuftonboro
This cottage in Tuftonboro has received excellent ratings for its location, cleanliness, and amenities. It is a great choice for travelers looking for a comfortable and convenient place to stay while exploring the area.
The cottage has one bathroom and can accommodate up to five guests. It features a fully equipped kitchen with a fridge and freezer, as well as parking and internet access.
Quaint Ossipee Home - Ossipee, NH
9.9 72 reviews

Quaint Ossipee Home

apartment, Ossipee
This apartment in Ossipee is located just a short distance from White Lake State Park, with Indian Mound Golf Course directly across the street, offering a convenient and scenic setting for your stay. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience.
The apartment has three bedrooms and one bathroom, comfortably accommodating up to six guests. Enjoy amenities like a fully equipped kitchen, air conditioning, a garden, parking for up to seven cars, and access to the internet, making your stay relaxing and enjoyable.
Soak & Stay Hot Tub Firepit Game Room Lakes Region - Ossipee, NH
10 41 reviews

Soak & Stay Hot Tub Firepit Game Room Lakes Region

apartment, Ossipee
This lakeside rental in Center Ossipee, NH, offers direct access to Mill Pond with a private dock, beach, and swim raft, approximately 1.5 hours north of Boston.
The 1,200-square-foot apartment features four bedrooms, two bathrooms, sleeps eight, and includes a renovated barn with a game room, plus kayaks, paddleboards, and a fully fenced dog pen for guest use.

Best Ossipee, NH vacation rentals with air conditioning

Bayside Sunshine - Ossipee, NH
No reviews

Bayside Sunshine

house, Ossipee
Bayside Sunshine, a 680 sq ft vacation home in Freedom, is located 23 miles from Kahuna Laguna and 30 miles from Story Land Amusement Park, with mountain views and proximity to White Mountain National Forest. This home offers guest capacity for 7, a well-equipped kitchen with a fridge, microwave, and dishwasher, a terrace, balcony with an outdoor fireplace, and is within walking distance to local amenities and the town center.
Tranquil Lakefront Cottage With Private Beach, Boat Slip & Fishing Kayak Access - Ossipee, NH
9.2 33 reviews

Tranquil Lakefront Cottage With Private Beach, Boat Slip & Fishing Kayak Access

cottage, Ossipee
This cottage is located in The Bays neighborhood of Center Ossipee, offering waterfront access on Leavitt Bay and is just a short drive from attractions like Sap House Meadery and Ossipee Lake Marina.
This 680 sq ft lakeside retreat sleeps up to 6 guests and features 2 bedrooms, 1 bathroom, a full kitchen with a dishwasher, air conditioning, a private sandy beach with a dock and boat slip (seasonal), a firepit, and two kayaks.
Ossipee Lake House - Ossipee, NH
9.5 11 reviews

Ossipee Lake House

apartment, Ossipee
This lakefront home in Deer Cove on Ossipee Lake offers stunning sunrise views over the lake and surrounding mountains, with easy access to the lake's main recreational areas.
The three-bedroom, one-bathroom house sleeps six guests and features a 70-foot private sandy beach, a dock (advance notice required), and amenities including a refrigerator, microwave, air conditioning, and parking.
Cozy Mountain Cabin For Quiet Getaway - Ossipee, NH
9.9 39 reviews

Cozy Mountain Cabin For Quiet Getaway

cabin, Ossipee
This Ossipee cottage is conveniently located a short drive from Conner Pond, Bayle Mountain, Chocorua, the Indian Mound Golf Club, and King Pine Ski Area, with easy access to North Conway's attractions.
The two-bedroom, one-bathroom rental sleeps four guests and features a fully equipped kitchen with an air fryer and crock-pot, a screened porch, a fire pit, and a washer/dryer; two queen beds provide comfortable sleeping arrangements.

Frequently Asked Questions about vacation rentals in Ossipee, NH

  • What are some interesting places to visit in or near Ossipee, NH?

    Ossipee is a great base for exploring the Lakes Region. You can visit the historic Ossipee Mountain Fire Tower for amazing views of the surrounding area, or take a scenic drive along the Kancamagus Highway. For a fun day trip, head to the charming town of Wolfeboro, known for its beautiful lakefront and quaint shops.
  • What are the best Airbnb and vacation rentals in Ossipee, NH?

    Econo Lodge Lakes Region, Heaven On The Water Every Season and Leavitt Road Cottages are the most popular Airbnb and vacation rentals in Ossipee, NH among travelers.

  • Which walking or cycling routes are the best in Ossipee, NH?

    The Ossipee Town Forest offers several miles of hiking trails, including the popular Bald Mountain Trail. For a leisurely bike ride, try the scenic route along Route 16, which winds through the heart of Ossipee. You can also check out the paved bike path along the Ossipee River.
  • What are the most popular Airbnbs in Ossipee, NH?

    Among the Airbnbs in Ossipee, NH, Heaven On The Water Every Season, Ossipee Lake Waterfront Condo and White Mountains Getaway are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Ossipee, NH?

    Ossipee is a haven for outdoor enthusiasts. You can enjoy swimming, boating, and fishing on Lake Ossipee, go hiking and mountain biking in the surrounding forests, or try your hand at kayaking or canoeing on the Ossipee River. In the winter, there's snowshoeing, cross-country skiing, and ice skating.
  • What are the best vacation rentals with a pool in Ossipee, NH?

  • What other towns or cities can be easily accessed from Ossipee, NH?

    Ossipee is conveniently located near several other towns and cities in the Lakes Region. You can easily drive to Wolfeboro, Conway, and Center Harbor, each with its own unique charm and attractions. For a bigger city experience, you can head to Manchester or Concord, both about an hour's drive away.
  • What are the best rentals for families and kids in Ossipee, NH?

  • What amenities are commonly available in vacation rentals in Ossipee, NH?

    Vacation rentals in Ossipee often come with amenities like fully equipped kitchens, comfortable living spaces, and private decks or patios. Many also offer access to shared amenities like pools, hot tubs, and fire pits. You can find rentals with a range of features, from cozy cabins to spacious lakefront homes.
  • What are the best rentals or Airbnbs with a jacuzzi in Ossipee, NH?

  • What time of year is best to rent a vacation rental Ossipee, NH?

    The best time to visit Ossipee depends on your preferences. Summer is popular for swimming, boating, and hiking, while fall offers stunning foliage and cooler temperatures. Winter is great for snow sports, and spring brings a fresh start with blooming wildflowers.

Popular destinations

Best Vacation Rentals with Balconies in Ossipee, NH

Elevate your stay in Ossipee, NH with a vacation rental featuring a private balcony and stunning city skyline views.

Kenny - Ossipee, NH
8.5 2 reviews

Kenny

house, Wolfeboro
This Wolfeboro vacation home is located 1.5 miles from Allen's Albee Beach and 47 miles from Portsmouth International Airport at Pease, offering convenient access to both recreation and travel.
This 1400-square-foot house features two bedrooms, two bathrooms, and accommodates up to 13 guests, complete with a fully equipped kitchen, Wi-Fi, a private garden, and on-site playground.
Country Dog Friendly Lake House W/ Access To Beaches, Tennis & Pickleball - Ossipee, NH
8.8 5 reviews

Country Dog Friendly Lake House W/ Access To Beaches, Tennis & Pickleball

apartment, Tuftonboro
This 1360 sq ft apartment in Tuftonboro, NH, offers countryside living near Lake Winnipesaukee, with two beaches, tennis courts, and fishing accessible within walking distance.
This pet-friendly rental accommodates up to 8 guests and features a kitchen with a fridge and microwave, a terrace, a garden, and parking, with nearby attractions including Lake Winnipesaukee, Albee Beach, and Castle in the Clouds.
Newly Renovated Rustic Cabin - Ossipee, NH
9.6 269 reviews

Newly Renovated Rustic Cabin

cabin, Tamworth
This Tamworth cabin is located just a short distance from White Lake State Park, offering easy access to nature trails, swimming, and boating. The cabin has consistently received excellent ratings from guests, making it a popular choice for those seeking a relaxing getaway.
The cabin has three bedrooms and one bathroom, comfortably accommodating up to six guests in its 1000 square feet of space. Enjoy amenities like a fully equipped kitchen, fireplace, outdoor barbecue grill, and access to the lake for a memorable vacation experience.
New! Woodland Retreat - Hot Tub Game Room Firepit - Ossipee, NH
10 2 reviews

New! Woodland Retreat - Hot Tub Game Room Firepit

house, Tamworth
This Tamworth vacation home is located near Story Land amusement park (28 miles) and White Mountain National Forest (29 miles), offering easy access to family-friendly attractions.
This four-bedroom, two-bathroom house sleeps up to 31 guests and boasts a private hot tub, fire pit, game room with billiards and darts, fully equipped kitchen, outdoor dining area, free Wi-Fi, and free parking.

Top Vacation Rentals for Families in Ossipee, NH

The right family vacation rental in Ossipee, NH makes all the difference, keeping you close to top city attractions.

Ossipee Lakefront-broad Bay! Taking Fall And Winter Reservations! - Ossipee, NH
10 32 reviews

Ossipee Lakefront-broad Bay! Taking Fall And Winter Reservations!

apartment, Ossipee
This five-bedroom Ossipee vacation home, located in The Bays, offers easy access to attractions like Sap House Meadery, Ossipee Lake Trail, Bearcamp River, King Pine Ski Area, and Ossipee Lake, all within a 9-12 mile radius.
The 3-bathroom house sleeps up to 18 guests and features a fully equipped kitchen, Jacuzzi, fireplace, Wi-Fi, outdoor garden with barbecue grills, and parking; nearby activities include hiking, skiing, and mead tasting.
3 Bdrm + Game Room - Lake, Ski, Hike, Shop! - Ossipee, NH
10 45 reviews

3 Bdrm + Game Room - Lake, Ski, Hike, Shop!

cabin, Freedom
This newly renovated three-bedroom Freedom, NH, lodge is a two-minute drive from Ossipee Lake's private beach and 25 minutes from North Conway, offering easy access to King Pine, Wildcat, Cranmore, and Attitash ski resorts.
The spacious home sleeps six, features two bathrooms, a fully equipped kitchen with dishwasher, a game room, a three-season sunroom, high-speed Wi-Fi, and provides paddleboards for lake activities, a firepit, and a grill for outdoor enjoyment.
Vacation Home Near Golf, Skiing, Shopping, & Private Beach Club At Lake Ossipee - Ossipee, NH
10 33 reviews

Vacation Home Near Golf, Skiing, Shopping, & Private Beach Club At Lake Ossipee

apartment, Freedom
This Freedom, New Hampshire vacation home is located 0.6 miles from Ossipee Lake Marina and within 6 miles of both Ossipee Lake and King Pine Ski Area, offering easy access to water activities, boating, and skiing.
This three-bedroom, two-bathroom house sleeps seven, features a fully equipped kitchen with appliances including a refrigerator and microwave, free WiFi, a DVD player, and a terrace/balcony with on-site barbecue grills.
New! Secluded Mountain Cabin W Stunning Views - Ossipee, NH
10 4 reviews

New! Secluded Mountain Cabin W Stunning Views

apartment, Ossipee
The Pocket Mountain Cabin sits atop Pocket Mountain in Ossipee's Granite section, a short drive from Province Lake and its golf course, and approximately 20 minutes from Wolfeboro.
This two-bedroom, two-bathroom lodge sleeps six, offering a queen bedroom upstairs, two downstairs bedrooms (one queen, one with two twins and two trundle beds), a full kitchen, Wi-Fi, pet-friendliness, outdoor amenities including a deck with grill, patio, and fire pit, and flexible sleeping arrangements with connecting barn doors.

Best Ossipee, NH vacation rentals with parking

Ossipee Retreat - Ossipee, NH
9.5 93 reviews

Ossipee Retreat

chalet, Freedom
The Ossipee Overlook | Spacious And Stunning Views - Ossipee, NH
9.9 21 reviews

The Ossipee Overlook | Spacious And Stunning Views

apartment, Ossipee
Cassie Cove Cottage On Ossipee - Ossipee, NH
10 7 reviews

Cassie Cove Cottage On Ossipee

apartment, Ossipee
Handcrafted Home In Ossipee, Near Lakes & Mts - Ossipee, NH
No reviews

Handcrafted Home In Ossipee, Near Lakes & Mts

apartment, Ossipee

Compare Luxury Vacation Rentals in Ossipee, NH

Elevate your travel experience with a luxury rental in Ossipee, NH, where high-end design meets a prime location.

Dog-friendly Cottage W/free Wifi, Kayak, Firepit, And Wood Stove - Ossipee, NH
No reviews

Dog-friendly Cottage W/free Wifi, Kayak, Firepit, And Wood Stove

apartment, Ossipee

Our Favorite Pet-Friendly Vacation Rentals in Ossipee, NH

Discover dog-friendly vacation rentals in Ossipee, NH situated perfectly for city walks and nearby dog parks.

The Wolfeboro House - Ossipee, NH
9.0 2 reviews

The Wolfeboro House

house, Wolfeboro
Our Mountain Retreat  Lake Ossipee Access - Ossipee, NH
9.8 114 reviews

Our Mountain Retreat Lake Ossipee Access

apartment, Freedom
Cozy Cabin Near Tuftonboro & Lake Winnipesaukee - Ossipee, NH
9.8 7 reviews

Cozy Cabin Near Tuftonboro & Lake Winnipesaukee

apartment, Tuftonboro
Spacious, Renovated 2-bedroom Home On Golf Course! - Ossipee, NH
9.8 66 reviews

Spacious, Renovated 2-bedroom Home On Golf Course!

apartment, Ossipee

Explore Vacation Rentals with a Pool in Ossipee, NH

Choose an Ossipee, NH rental with a pool for a refreshing swim right in the heart of the city.

Nh Country Retreat And Family Reunions - Ossipee, NH
9.7 147 reviews

Nh Country Retreat And Family Reunions

apartment, Tamworth

Search Vacation Rentals with Jacuzzi in Ossipee, NH

Unwind at the end of a busy city day with a private hot tub at these hand-selected vacation rentals in Ossipee, NH.

Waterfront Home On The Beach. Ossipee Lake - Ossipee, NH
9.8 18 reviews

Waterfront Home On The Beach. Ossipee Lake

apartment, Ossipee
Cozy & Modern A-frame In The Woods W/hot Tub - Ossipee, NH
10 1 review

Cozy & Modern A-frame In The Woods W/hot Tub

chalet, Tamworth
Stagecoach Nh Riverfront Access - Ossipee, NH
No reviews

Stagecoach Nh Riverfront Access

house, Tamworth
White Mountain Getaway - Ossipee, NH
No reviews

White Mountain Getaway

house, Ossipee
©2026 cozycozy.com