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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Ossipee holiday 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 AU$645
includes taxes & fees
31 Aug - 1 Sept
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, (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 AU$652
includes taxes & fees
31 Aug - 1 Sept
Cozy Tuftonboro Escape: Steps to Private Beaches!
A lake with a sandy beach and a concrete dock extending into the water.

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 AU$653
includes taxes & fees
22 Sept - 23 Sept
Private Pond Cabin with Lake Access & Fire Pit
A garden with a white pergola, red chairs, and pink flowers.

4. 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 AU$320
includes taxes & fees
25 Aug - 26 Aug
Cottage 4 - Year Round Pet Friendly $50 Fee 1 Bed w/ Loft / 1 Bath & Courtyard
A tent with a bed, two chairs, and a small table on a wooden deck surrounded by trees.

5. 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 AU$260
includes taxes & fees
25 Aug - 26 Aug
Luxury Tent in New Hampshire-Tail-Tuckaway

6. 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 AU$266
includes taxes & fees
26 Aug - 27 Aug
Reconnect with Nature at this Glamping Tent in East Wakefield, New Hampshire
A cabin with a picnic table and a fire pit, surrounded by large rocks and trees, overlooking a lake with boats.

7. 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 AU$252
includes taxes & fees
1 Sept - 2 Sept
Danforth Bay Camping and RV Resort
A serene lakeside view at sunset with a silhouette of trees and a calm water surface.

8. 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
10.0 out of 10, Exceptional, (20 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is AU$327
includes taxes & fees
16 Sept - 17 Sept
Cottage 12 - Year Round - Pet Friendly $50 Fee -1 King Bed / 1 Bath & Courtyard
A two-story house with a white front porch, a staircase, and a garage.

9. 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 AU$255
includes taxes & fees
26 Aug - 27 Aug
Caretakers -Split level Pet Friendly $50 Fee
A modern living room with a fireplace, a television, and a comfortable seating area.

10. 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.
Cozy three bedroom house located just five minutes from Lake Winnipesaukee
A deck with a view of a frozen lake and surrounding trees.

11. 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 AU$468
includes taxes & fees
20 Sept - 21 Sept
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
A wooden dock with a hammock and chairs by a lake surrounded by autumn foliage.

12. 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 AU$879
includes taxes & fees
1 Sept - 2 Sept
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
A coastal town with a marina, a large cruise ship docked, and a beach.

13. 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 AU$315
includes taxes & fees
8 Sept - 9 Sept
Delightful cabin lake views & access now featuring AC Wi-FI and TV sleeps 3
A wooden interior with a round wooden table and a red macramé hanging chair.

14. 1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
Shapleigh
8.8 out of 10, Excellent, (5 reviews)
"Stayed for 2 nights and had a wonderful relaxing time. Very kind and repsonsive hosts. We especially loved the fire pit. Would stay again in a heart beat. "
United States
Bethany K.
The price is AU$223
includes taxes & fees
26 Aug - 27 Aug
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
A modern kitchen with white cabinets, a microwave, and a stove.

15. Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Alton
10.0 out of 10, Exceptional, (1 review)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
The price is AU$327
includes taxes & fees
14 Sept - 15 Sept
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
A stone patio with a picnic table, a white fence, and a house with a view of a lake.

16. Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Alton
9.0 out of 10, Wonderful, (22 reviews)
"Great little gem given its price, location, and overall accommodations! "
United States
Kevin R.
The price is AU$454
includes taxes & fees
8 Sept - 9 Sept
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
A well-maintained lawn with a flagpole, neatly trimmed hedges, and a residential building in the background.

17. Cozy hotel-style suite right on the water, shared patio, free WiFi

Cozy hotel-style suite right on the water, shared patio, free WiFi
Alton
9.0 out of 10, Wonderful, (19 reviews)
"One of our favorite places to stay in this area."
United States
Anthony G.
The price is AU$454
includes taxes & fees
8 Sept - 9 Sept
Cozy hotel-style suite right on the water, shared patio, free WiFi
A small cabin with a porch, surrounded by trees and a body of water.

18. Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Alton
8.6 out of 10, Excellent, (20 reviews)
"Nice location on the lake."
United States
Mary L.
The price is AU$492
includes taxes & fees
8 Sept - 9 Sept
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
A cozy room with a wicker sofa, a wooden ladder shelf, and a large wooden-framed window.

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 AU$486
includes taxes & fees
21 Sept - 22 Sept
Newly Renovated Cottage 4 in Alton Bay, NH
A rustic cabin interior with a dining area, a sofa, and a coffee table.

20. Artsy Woodland Group Hideaway Cabin!

Artsy Woodland Group Hideaway Cabin!
Parsonsfield
8.0 out of 10, Very good, (11 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 AU$729
includes taxes & fees
25 Aug - 26 Aug
Artsy Woodland Group Hideaway Cabin!
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

Days Inn by Wyndham Tamworth

Days Inn by Wyndham Tamworth

8/10 Good
"The bathroom door was in need of repair it barely closed. No cups for coffee or water in the room."
Janice 1-night trip
Posted less than an hour ago
Days Inn by Wyndham Tamworth

Find out more about Ossipee

Everything you need to know about Ossipee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ossipee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ossipee holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Ossipee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ossipee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ossipee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ossipee holiday rentals we have selected for you start as low as AU$324 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Ossipee rentals

At Expedia, we put the best Ossipee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ossipee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ossipee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ossipee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beach House on the Big Lake with 90-foot dock. Bring your boat! New listing!: This holiday home rental outside of Ossipee is located on the beach, and has a patio, 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. You can relax into your holiday with a selection of games and 1 hot tub.

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 Duncan Lake. In the wider area, you’ll find Lake Winnipesaukee and Ossipee Lake Trail.

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.