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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Ossipee holiday rentals

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

1. 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$1,111
HK$1,385 total
includes taxes & fees
29 Oct - 30 Oct
Cottage 3 - Year Round - Pet Friendly $50 Fee - 1 Bedroom / 1 Bath
A cabin with a picnic table and a fire pit, surrounded by large rocks and trees, overlooking a lake with boats.

2. 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$1,308
HK$1,419 total
includes taxes & fees
15 Oct - 16 Oct
Danforth Bay Camping and RV Resort
A garden with a white pergola, red chairs, and pink flowers.

3. 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$1,102
HK$1,366 total
includes taxes & fees
18 Oct - 19 Oct
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
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$1,295
HK$3,721 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A spacious kitchen with wooden beams, a large dining table, and a fireplace.

5. 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$1,664
HK$3,628 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A two-story house with a white front porch, a staircase, and a garage.

6. 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$1,045
HK$1,304 total
includes taxes & fees
29 Oct - 30 Oct
Caretakers -Split level Pet Friendly $50 Fee
A garden with various plants and trees, including a prominent cactus and some flowering plants.

7. 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$941 total
includes taxes & fees
20 Oct - 21 Oct
1 of 2 Cozy Cabins on Sloaping Forested Land
A spacious kitchen with a large island, white cabinetry, and a view of a playground through large windows.

8. 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, (7 reviews)
"Staff was very freindly"
United States
David
The price is HK$910
HK$1,847 total
includes taxes & fees
27 Oct - 28 Oct
Newly Renovated Cottage 3 on Main Street Alton Bay!
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.
The price is HK$1,060
HK$2,580 total
includes taxes & fees
1 Nov - 2 Nov
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
A cozy room with a wicker sofa, a wooden ladder shelf, and a large wooden-framed window.

10. Newly Renovated Cottage 4 in Alton Bay, NH

Newly Renovated Cottage 4 in Alton Bay, NH
Alton
9.0 out of 10, Wonderful, (4 reviews)
"Communication was amazing, check in was a delightful, the house itself was perfect "
United States
Jennifer S.
Newly Renovated Cottage 4 in Alton Bay, NH
A house with a porch, surrounded by a garden with pink and yellow flowers.

11. 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$1,083
HK$1,345 total
includes taxes & fees
22 Oct - 23 Oct
Cottage 7 - Year Round - Pet Friendly $50 Fee - Stand Alone 1 Bedroom / 1 Bath
A serene lakeside view at sunset with a silhouette of trees and a calm water surface.

12. 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$1,196
HK$1,485 total
includes taxes & fees
18 Oct - 19 Oct
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A lakeside property with a dock, boats, and a large building surrounded by trees.

13. Gilford Perfect Getaway Pool, WIFI & Free Parking

Gilford Perfect Getaway Pool, WIFI & Free Parking
Laconia
8.4 out of 10, Very good, (7 reviews)
"Very nice place, easily located near everything. Would definitely stay here again."
United States
Katherine B.
Gilford Perfect Getaway Pool, WIFI & Free Parking
A golf course with a pond, surrounded by trees with autumn foliage.

14. 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, (8 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$1,215
HK$1,505 total
includes taxes & fees
18 Oct - 19 Oct
Cottage 11 - Year Round - Pet Friendly $50 Fee- 1 Bed / 1 Bath w/ Courtyard
A cozy living room with a brown leather sofa, a wooden coffee table, and a fish-themed wall decoration.

15. 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 wooden cabin interior with a dining table, chairs, a kitchen area with cabinets, and a door with a window.

16. Hiking & Snowmobile Trails On-Site: Alton Retreat!

Hiking & Snowmobile Trails On-Site: Alton Retreat!
Alton
10.0 out of 10, Exceptional, (9 reviews)
"Perfect little spot. Clean, comfy everything you need and then some. Thanks for hosting us."
United States
Matthew M.
The price is HK$895
HK$2,410 total
includes taxes & fees
18 Oct - 19 Oct
Hiking & Snowmobile Trails On-Site: Alton Retreat!
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$1,342
HK$1,555 total
includes taxes & fees
27 Oct - 28 Oct
Reconnect with Nature at this Glamping Tent in East Wakefield, New Hampshire
A waterfront area with a large white building, a dock with boats, and a clock tower in the background.

18. 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 HK$1,252
HK$1,555 total
includes taxes & fees
3 Nov - 4 Nov
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath
A living room with a stone fireplace, a ceiling fan, and a large window.

19. 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$1,044
HK$3,534 total
includes taxes & fees
5 Nov - 6 Nov
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
A beach with picnic tables and lounge chairs, a stone wall, and a view of the lake and distant mountains.

20. Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Gilford
9.8 out of 10, Exceptional, (35 reviews)
"Great location, specially for concerts or enjoying the beach. Some road noise."
United States
Estuardo
The price is HK$1,067
HK$2,129 total
includes taxes & fees
4 Nov - 5 Nov
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
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

Weirs Beach Motel and Cottages

Weirs Beach Motel and Cottages

8/10 Good
"The room was clean except for a used towel hanging on the back of the bathroom door. I had to bring my dogs with me at the last minute, and they were very accommodating and helpful. The self-check in process was very easy and the location is great if you want to enjoy the lakefront and Laconia."
Christina 1-night trip
Posted 1 hour ago
Weirs Beach Motel and Cottages

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.