A boat on a calm lake at sunset with mountains in the background.

Ossipee Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Ossipee vacation rentals

A spacious kitchen with wooden beams, a large dining table, and a fireplace.

1. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
3.0 star property
Tuftonboro
10.0 out of 10, Exceptional, (2 reviews)
"We’ll kept "
United States
Denise
The price is AED 779
AED 1,698 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dining table with a placemat and a bowl.

2. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
Center Tuftonboro
10.0 out of 10, Exceptional, (16 reviews)
"Property was just as pictured. Great location near the pond. Home had everything I could have needed, including a few snacks. Bit of a snafu on check-in but host communication was quick and pleasant!"
United States
Diane S.
The price is AED 606
AED 1,742 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A cabin with a picnic table and a fire pit, surrounded by large rocks and trees, overlooking a lake with boats.

3. Danforth Bay Camping and RV Resort

Danforth Bay Camping and RV Resort
2.0 star property
Freedom
8.4 out of 10, Very good, (16 reviews)
"Definitely will stay again. Basic cabin but great location"
United States
Jacqui
The price is AED 612
AED 664 total
includes taxes & fees
13 Oct - 14 Oct
Danforth Bay Camping and RV Resort
A serene lakeside view at sunset with a silhouette of trees and a calm water surface.

4. Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (22 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is AED 560
AED 691 total
includes taxes & fees
19 Oct - 20 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A rustic cabin interior with a dining area, a sofa, and a coffee table.

5. Artsy Woodland Group Hideaway Cabin!

Artsy Woodland Group Hideaway Cabin!
Parsonsfield
8.0 out of 10, Very good, (13 reviews)
"It's not the most modern place but it is a good value, has what you need and is in a beautiful setting "
United States
Dan F.
The price is AED 1,405
AED 1,928 total
includes taxes & fees
11 Oct - 12 Oct
Artsy Woodland Group Hideaway Cabin!
A garden with a white pergola, red chairs, and pink flowers.

6. Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (14 reviews)
"Great place "
United States
Anonymous traveler
The price is AED 516
AED 639 total
includes taxes & fees
12 Oct - 13 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A two-story house with a white front porch, a staircase, and a garage.

7. Caretakers -Split level Pet Friendly $50 Fee

Caretakers -Split level Pet Friendly $50 Fee
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"I would stay there again. The caretakers place was just adorable. My stay was very relaxing and the place offered so many activities for children and adults. "
United States
Judith
The price is AED 489
AED 611 total
includes taxes & fees
22 Oct - 23 Oct
Caretakers -Split level Pet Friendly $50 Fee
Living area

8. Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access

Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access
Newfield
10.0 out of 10, Exceptional, (5 reviews)
"I stayed here for the 4th of July weekend and had a wonderful time! You can really tell the host put a lot of thought and detail to every little thing on the inside and outside. There was a lot of nice features throughout like the hidden sauna, hot tub, fire pit, swinging chairs, etc. "
United States
Stephanie S.
The price is AED 1,142
AED 1,818 total
includes taxes & fees
15 Oct - 16 Oct
Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access
A deck with a view of a frozen lake and surrounding trees.

9. A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
Freedom
8.8 out of 10, Excellent, (36 reviews)
"Helen was very quick to answer any questions we had. The house was very clean and the bed was very comfortable!"
United States
Connie S.
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
A covered outdoor seating area with a view of a lake, a sofa, a table, and string lights.

10. Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain

Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
Moultonborough
9.8 out of 10, Exceptional, (103 reviews)
"Great location, very quiet and relaxing"
United States
Thiago S.
The price is AED 2,149
AED 3,348 total
includes taxes & fees
12 Oct - 13 Oct
Pet friendly, private sandy beach/dock, Spectacular Winnipesaukee Lake/Mountain
A cozy living room with a brown leather sofa, a wooden coffee table, and a fish-themed wall decoration.

11. Lake Winnipesaukee Home for Fall & Winter Fun

Lake Winnipesaukee Home for Fall & Winter Fun
3.0 star property
Moultonborough
Lake Winnipesaukee Home for Fall & Winter Fun
A dining area with a wooden table and chairs, a clock on the wall, and a window with blinds.

12. Cozy 3-bedroom chalet in charming Tamworth next to Whit Lakes state park/beach

Cozy 3-bedroom chalet in charming Tamworth next to Whit Lakes state park/beach
Tamworth
10.0 out of 10, Exceptional, (2 reviews)
"Very well looked after property with lots of adequate supplies. We enjoyed a variety of teas and coffee pods, there were lots of my blankets and towels, very well stocked. The beds were extremely comfortable- had the best sleep in months on a good mattress and soft down pillows."
United States
gautam
The price is AED 915
AED 1,837 total
includes taxes & fees
13 Oct - 14 Oct
Cozy 3-bedroom chalet in charming Tamworth next to Whit Lakes state park/beach
A garden with a white pergola, red chairs, and pink flowers.

13. Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath

Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath
Wolfeboro
10.0 out of 10, Exceptional, (4 reviews)
"Everything was great!"
United States
Leah F.
The price is AED 771
AED 956 total
includes taxes & fees
13 Oct - 14 Oct
Cottage 8-9 - Year Round - Pet Friendly $50 Fee- Stand Alone 2 Bedroom / 2 Bath
A garden with a white pergola, red chairs, and pink flowers.

14. Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (6 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is AED 507
AED 630 total
includes taxes & fees
12 Oct - 13 Oct
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A waterfront area with a large white building, a dock with boats, and a clock tower in the background.

15. Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath

Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"We had a perfect stay. Super cute cabin, clean and very comfortable.We thoroughly enjoyed or time there. Very easy process and would absolutely recommend and book again."
United States
Jessica G.
The price is AED 586
AED 728 total
includes taxes & fees
1 Nov - 2 Nov
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

16. Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...

Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
Alton
10.0 out of 10, Exceptional, (5 reviews)
"Best communication ever at a VRBO. When I come back, I’m there!"
United States
shaun d.
The price is AED 680
AED 1,518 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A living room with a beige sofa, a wooden coffee table, and a large window with a view of a balcony.

17. Newly Renovated Cottage 7 in Alton Bay

Newly Renovated Cottage 7 in Alton Bay
Alton
10.0 out of 10, Exceptional, (2 reviews)
"Host was responsive and the property was just close enough to enjoy laconia without a huge price premium. Its a simple cabin, but it did what we needed it to do. Gravel parking lot is not the best for motorcycles if i had to leave constructive feedback. Would rent again."
United States
fred j.
The price is AED 1,183
AED 1,829 total
includes taxes & fees
23 Oct - 24 Oct
Newly Renovated Cottage 7 in Alton Bay
Living area

18. Lotus Spa, your home away from home

Lotus Spa, your home away from home
Acton
10.0 out of 10, Exceptional, (63 reviews)
"Really nice stay at a cute property. Would go back!"
United States
Christopher D.
Lotus Spa, your home away from home
A spacious living room with a wooden ceiling, large windows, a sofa, a coffee table, and a fireplace.

19. Gunstock Chalet - 4BR, Skiing, Concerts, Hiking, & Fall Foliage

Gunstock Chalet - 4BR, Skiing, Concerts, Hiking, & Fall Foliage
Gilford
10.0 out of 10, Exceptional, (5 reviews)
"Very clean and well appointed property. Kitchen well stocked and bathrooms very nice to use. Very pleasant to just stay in and enjoy the property. We could have stayed longer. Communication was easy and quick feedback. Owners provided useful information on the area on things to do and places to go. Would definitely stay there again if in that area."
United States
Todd B.
The price is AED 830
AED 1,997 total
includes taxes & fees
1 Nov - 2 Nov
Gunstock Chalet - 4BR, Skiing, Concerts, Hiking, & Fall Foliage
A beach with sand, trees, and a boat in the background.

20. 5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!

5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!
Gilford
9.8 out of 10, Exceptional, (25 reviews)
"Was a great place to stay. Had a great time "
United States
Ryan C.
The price is AED 1,416
AED 3,054 total
includes taxes & fees
12 Oct - 13 Oct
5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossipee Hotel Reviews

The Green Granite North Conway, an Ascend Collection Hotel

The Green Granite North Conway, an Ascend Collection Hotel

8/10 Good
"Très bien situé, a 2 pas des ourlets. Le déjeuner est redondant et pas très garni."
Eric 2-night trip
Posted 1 hour ago
The Green Granite North Conway, an Ascend Collection Hotel

Frequently asked questions

Can I find a vacation rental in Ossipee?

Yes, we offer vacation rentals close to the most popular points of interest in Ossipee, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Ossipee?

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This vacation home rental outside of Ossipee is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Ossipee?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Ossipee stay.

What’s there to see and do in Ossipee?

While exploring the area, visit family-friendly sights like Libby Museum, or get outside and enjoy nature at Duncan Lake. In the larger area, you’ll find Ossipee Lake Trail and Lake Wentworth.

What’s a vacation rental in Ossipee like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Ossipee. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for family gatherings.