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

Ossipee Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Ossipee holiday rentals

A garden with a white pergola, red chairs, and pink flowers.

1. 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 traveller
The price is HK$1,120
HK$1,385 total
includes taxes & fees
2 Nov - 3 Nov
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A garden with a white pergola, red chairs, and pink flowers.

2. 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 HK$1,120
HK$1,385 total
includes taxes & fees
2 Nov - 3 Nov
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A cabin with a bunk bed, a window, and a patterned rug.

3. 1 of 2 Cozy Cabins on Sloaping Forested Land

1 of 2 Cozy Cabins on Sloaping Forested Land
Shapleigh
10.0 out of 10, Exceptional, (3 reviews)
"Everything was excellent!!"
United States
Maja R.
The price is HK$706
HK$940 total
includes taxes & fees
2 Nov - 3 Nov
1 of 2 Cozy Cabins on Sloaping Forested Land
A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a dining table with a placemat and a bowl.

4. 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 HK$1,294
HK$3,720 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A two-story house with a white front porch, a staircase, and a garage.

5. 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 HK$1,035
HK$1,293 total
includes taxes & fees
28 Oct - 29 Oct
Caretakers -Split level Pet Friendly $50 Fee
A deck with a view of a frozen lake and surrounding trees.

6. 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.
The price is HK$981
HK$2,486 total
includes taxes & fees
20 Nov - 21 Nov
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
A modern living room with a flat-screen TV, a grey sofa with a 'together' pillow, a wooden coffee table with a plant and board games, and an air conditioning unit on the wall.

7. Hidden Gem Near Castle in the Clouds [Pet Friendly-WiFi-Enclosed Private Porch]

Hidden Gem Near Castle in the Clouds [Pet Friendly-WiFi-Enclosed Private Porch]
Tuftonboro
8.0 out of 10, Very good, (1 review)
"Clean, pet friendly, quiet, attractively furnished. Had not known it would be a second floor unit with stairs to enter. That was not a problem for us but might be for others. We enjoyed ourselves."
United States
Carola B.
The price is HK$1,294
HK$2,093 total
includes taxes & fees
2 Nov - 3 Nov
Hidden Gem Near Castle in the Clouds [Pet Friendly-WiFi-Enclosed Private Porch]
A spacious kitchen with wooden beams, a large dining table, and a fireplace.

8. 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 HK$1,663
HK$3,626 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A tent with a bed, two chairs, and a small table on a wooden deck surrounded by trees.

9. Luxury Tent in New Hampshire-Tail-Tuckaway

Luxury Tent in New Hampshire-Tail-Tuckaway
Wakefield
10.0 out of 10, Exceptional, (2 reviews)
"Such an amazing experience, my partner and I stayed here while attending the Maine Renaissance faire in Acton (only 20 minutes away) and we couldn't have asked for a better experience! Definitely the most glamorous camping experience we've ever had haha, we can't wait to book again"
United States
Rebecca
The price is HK$1,176
HK$1,464 total
includes taxes & fees
28 Oct - 29 Oct
Luxury Tent in New Hampshire-Tail-Tuckaway
A living room with a stone fireplace, a ceiling fan, and a large window.

10. Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8

Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
Gilford
10.0 out of 10, Exceptional, (1 review)
"Home was clean Host was easy to communicate with"
United States
Robert L.
The price is HK$791
HK$3,249 total
includes taxes & fees
1 Nov - 2 Nov
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
A two-story house with a dark roof, multiple windows, and a porch with chairs.

11. Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available

Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available
Wolfeboro
7.2 out of 10, Good, (5 reviews)
"No way does this deserve a 10/10 rating. It’s fairly terrible and not deserving such a favorable rating. The pluses - great location, right on the lake. Adirondacks at sunset was heavenly. Super convenient. Wolfeboro is very cute. The shower has been nicely redone. The in-unit washer/dryer worked well and was very convenient. But the negatives are many. Lots of disrepair and terrible attention to detail. We got a spongy soft double bed. The listing says Queen bed. It’s not. We had badly stained...
United States
Brian L.
The price is HK$1,114
HK$2,298 total
includes taxes & fees
2 Nov - 3 Nov
Downtown Wolfeboro condo, right on Wolfeboro Bay/Winnipesaukee w/dock available
A large, modern building with multiple floors and a flat roof, surrounded by a snowy landscape and a body of water in the background.

12. Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!

Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
Weirs Beach
9.2 out of 10, Wonderful, (7 reviews)
"Property was very clean, had very comfortable beds and a wonderful view. "
United States
Crystal
Cute Lower Level Cedar Lodge Room with Balcony & Lake Views!
A cabin with a deck, picnic table, and fire pit, surrounded by trees and a lake.

13. 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 HK$1,450
HK$1,573 total
includes taxes & fees
30 Oct - 31 Oct
Danforth Bay Camping and RV Resort
A house with a porch, surrounded by a garden with pink and yellow flowers.

14. Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath

Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
Wolfeboro
9.0 out of 10, Wonderful, (8 reviews)
"Great location & comfortable! "
United States
Jeanine L.
The price is HK$1,101
HK$1,365 total
includes taxes & fees
4 Nov - 5 Nov
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A garden with a white pergola, red chairs, and pink flowers.

15. 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 HK$1,195
HK$1,475 total
includes taxes & fees
2 Nov - 3 Nov
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
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)
"We had a wonderful stay at the cozy cottage! The porch is very comfy and has great light. The beds were also very comfortable and kitchen was well stocked."
United States
Rebecca K.
The price is HK$1,451
HK$3,242 total
includes taxes & fees
1 Nov - 2 Nov
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
Property grounds

17. Reconnect with Nature at this Glamping Tent in East Wakefield, New Hampshire

Reconnect with Nature at this Glamping Tent in East Wakefield, New Hampshire
East Wakefield
The price is HK$1,341
HK$1,554 total
includes taxes & fees
28 Oct - 29 Oct
Reconnect with Nature at this Glamping Tent in East Wakefield, New Hampshire
A cozy interior of a yurt with a central wood-burning stove, a sofa, and a bed with floral bedding.

18. Ava Jade yurt nestled in the woods of Brownfield, Maine

Ava Jade yurt nestled in the woods of Brownfield, Maine
Brownfield
10.0 out of 10, Exceptional, (25 reviews)
"Great camping experience"
United States
Kathleen
The price is HK$863
HK$1,282 total
includes taxes & fees
29 Oct - 30 Oct
Ava Jade yurt nestled in the woods of Brownfield, Maine
A garden with a white pergola, red chairs, and pink flowers.

19. Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard

Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard
Wolfeboro
9.8 out of 10, Exceptional, (9 reviews)
"Had a great time at the cottages at Wolfeboro. Nice and relaxing stay for 2 nights"
United States
Connie S.
The price is HK$1,214
HK$1,504 total
includes taxes & fees
2 Nov - 3 Nov
Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard
A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

20. Newly Renovated Cottage 3 on Main Street Alton Bay!

Newly Renovated Cottage 3 on Main Street Alton Bay!
Alton
9.6 out of 10, Exceptional, (8 reviews)
"Staff was very freindly"
United States
David
The price is HK$1,122
HK$2,120 total
includes taxes & fees
1 Nov - 2 Nov
Newly Renovated Cottage 3 on Main Street Alton Bay!
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

Mill Falls Resort Collection at the Lake

Mill Falls Resort Collection at the Lake

10/10 Excellent
"The room had a beautiful view of the lake. Sitting of the porch and warming up by the fireplace when you come in was wonderful. Thebed and pillows were comfortable. The shower and bathroom were nice. We would return for another stay"
David 3-night trip
Posted 12 hours ago
Mill Falls Resort Collection at the Lake

Find out more about Ossipee

Search for holiday rentals in Ossipee on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossipee using one of the methods below:

  • View our selection of featured holiday rentals in Ossipee
  • Use the map to find apartments and other holiday homes in the Ossipee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ossipee while they last

Look no further and take a look at our great range of rental properties in Ossipee!

Frequently asked questions

Can I find a holiday rental in Ossipee?

Yes, there are holiday rentals close to the most popular sights in Ossipee, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Ossipee has to offer?

Stunning Waterfront Home with Boat Dock, swim, boating. Bike & skiing nearby.: This holiday home rental outside of Ossipee is located on a lake, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Ossipee?

With 7 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Ossipee Lake Trail and Lake Wentworth.

What’s a holiday rental in Ossipee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossipee. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.