Ossipee Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Ossipee holiday rentals

Private kitchen
9 Lake Street

Apartment in Wolfeboro

9 Lake Street
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is S$315
includes taxes & fees
16 Jan - 17 Jan, 2026
9 Lake Street
Exterior
Danforth Bay Camping and RV Resort

Camping in Freedom

Danforth Bay Camping and RV Resort
2.0 star property
8.4 out of 10, Very good, (15)
"Family- friendly Beautiful all around Soo many things to do you can never get bored Enjoyed every minute of it "
United States
Roxanna
Danforth Bay Camping and RV 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

The Windrifter Resort

The Windrifter Resort

10/10 Excellent
"Room was clean. Cute small kitchen with large refrigerator, microwave, 2 burner stove, some dishes, coffeemaker, etc. Had larger bathroom than expected. Had small samples of shampoo but no conditioners. Had some of my own. According to desk, the inn was a former farm house from the 1800s so don't expect a modern new place. Parking was fine. "
Sigute 1-night trip
Posted 7 days ago
The Windrifter Resort

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.

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 Stand Up Paddleboard NH, or get outside and enjoy nature at Ossipee Lake Trail. In the wider area, you’ll find Lake Wentworth and Province Lake Golf Course.

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.