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Ossipee Vacation Rentals

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Our top choices for Ossipee vacation rentals

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 CA $294
CA $641 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Tuftonboro Escape: Steps to Private Beaches!

2. Cozy Tuftonboro Escape: Steps to Private Beaches!

Cozy Tuftonboro Escape: Steps to Private Beaches!
Center Tuftonboro
10.0 out of 10, Exceptional, (15 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 CA $229
CA $649 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Tuftonboro Escape: Steps to Private Beaches!

3. Private Pond Cabin with Lake Access & Fire Pit

Private Pond Cabin with Lake Access & Fire Pit
Tuftonboro
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful property "
United States
Keith B.
The price is CA $240
CA $639 total
includes taxes & fees
Sep 22 - Sep 23
Private Pond Cabin with Lake Access & Fire Pit

4. 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 CA $208
CA $256 total
includes taxes & fees
Sep 2 - Sep 3
Luxury Tent in New Hampshire-Tail-Tuckaway

5. 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, (4 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 CA $241
CA $296 total
includes taxes & fees
Sep 2 - Sep 3
Cottage 10-Pet Friendly-1 Bedroom w/ Loft / 1 Bath

6. 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 CA $231
CA $251 total
includes taxes & fees
Sep 2 - Sep 3
Danforth Bay Camping and RV Resort

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, (2 reviews)
"Everything was excellent!!"
United States
Maja R.
The price is CA $125
CA $166 total
includes taxes & fees
Sep 8 - Sep 9
1 of 2 Cozy Cabins on Sloaping Forested Land

8. 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, (12 reviews)
"Great place "
United States
Anonymous traveller
The price is CA $231
CA $282 total
includes taxes & fees
Sep 8 - Sep 9
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard

9. Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
Alton
8.8 out of 10, Excellent, (14 reviews)
"Nicely kept enjoyable stay"
United States
Shirley G.
The price is CA $150
CA $311 total
includes taxes & fees
Sep 2 - Sep 3
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3

10. 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 CA $200
CA $247 total
includes taxes & fees
Sep 7 - Sep 8
Caretakers -Split level Pet Friendly $50 Fee

11. 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 CA $229
CA $260 total
includes taxes & fees
Sep 2 - Sep 3
Reconnect with Nature at this Glamping Tent in East Wakefield, New Hampshire

12. Newly Renovated Cottage on Main Street Alton Bay #5

Newly Renovated Cottage on Main Street Alton Bay #5
Alton
8.4 out of 10, Very good, (6 reviews)
"Great places. Quiet and quaint and close to the lake and restaurants. Will rent again "
United States
Brian B.
The price is CA $169
CA $343 total
includes taxes & fees
Sep 29 - Sep 30
Newly Renovated Cottage on Main Street Alton Bay #5

13. 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, (35 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 CA $208
CA $480 total
includes taxes & fees
Sep 20 - Sep 21
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!

14. Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro
10.0 out of 10, Exceptional, (20 reviews)
"We had the best time here, would 100% go back. Very quiet and relaxing and the hosts were great."
United States
The F.
The price is CA $405
CA $837 total
includes taxes & fees
Sep 2 - Sep 3
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

15. 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, (21 reviews)
"Great camping experience"
United States
Kathleen
The price is CA $152
CA $227 total
includes taxes & fees
Sep 2 - Sep 3
Ava Jade yurt nestled in the woods of Brownfield, Maine

16. Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Wolfeboro
7.2 out of 10, Good, (22 reviews)
"Thanks for a great stay!"
United States
Lynne Q.
The price is CA $312
CA $522 total
includes taxes & fees
Sep 5 - Sep 6
Cozy three bedroom house located just five minutes from Lake Winnipesaukee

17. Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (28 reviews)
"Everything was great. Very clean and comfortable! Thank you for a great place to stay. "
United States
Heather K.
The price is CA $175
CA $361 total
includes taxes & fees
Sep 9 - Sep 10
Rustic Rose Cottage of Historic West Lebanon

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

Hiking & Snowmobile Trails On-Site: Alton Retreat!
Alton
10.0 out of 10, Exceptional, (9 reviews)
"Such a cute place! Great amenities! Very cozy! Would definitely stay again! "
United States
Karolyn W.
The price is CA $170
CA $391 total
includes taxes & fees
Sep 25 - Sep 26
Hiking & Snowmobile Trails On-Site: Alton Retreat!

19. 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.
The price is CA $158
CA $497 total
includes taxes & fees
Sep 21 - Sep 22
Newly Renovated Cottage 4 in Alton Bay, NH

20. Cozy cottage get-away at Lake Winnipesaukee with swim access off dock

Cozy cottage get-away at Lake Winnipesaukee with swim access off dock
Alton
9.6 out of 10, Exceptional, (18 reviews)
"Cabin is in a great location, very quiet, very comfortable, with great features. Would definitely return again when I'm in the area."
United States
Barry
The price is CA $224
CA $448 total
includes taxes & fees
Sep 2 - Sep 3
Cozy cottage get-away at Lake Winnipesaukee with swim access off dock
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

Find out more about Ossipee

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ossipee. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Luxury Lake House with Sandy Beach, 90' Dock & Panoramic Lake Views: This vacation home rental outside of Ossipee is located on the beach and has a patio, 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. You can relax into your vacation with a selection of games and a hot tub.

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 Stand Up Paddleboard NH, or get outside and enjoy nature at Duncan Lake. In the larger area, you’ll find Lake Winnipesaukee and Ossipee Lake Trail.

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.