Ossipee Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Ossipee

Waterfront Cabin! Infloor heat, fireplace, Games, new hot tub mid Nov!

Merrifield
10.0 out of 10, Exceptional, (8)
"What a darling cottage that is decorated absolutely beautifully! They thought of every little amenity to make your visit more enjoyable! Would love to visit again when the landscaping is done and can enjoy warmer weather!"
United States
Kathy D.
The price is NZ$781
includes taxes & fees
11 Nov - 12 Nov
Waterfront Cabin! Infloor heat, fireplace, Games, new hot tub mid Nov!

Explore Crosslake: Lakeside Cabin for Unforgettable Family Escapes in Minnesota

Crosslake
The price is NZ$789
includes taxes & fees
10 Nov - 11 Nov
Explore Crosslake: Lakeside Cabin for Unforgettable Family Escapes in Minnesota

Nature Link Resort

3.0 star property
Nisswa
9.6 out of 10, Exceptional, (60)
"Second stay on the property and we enjoyed it even more this go round"
United States
Colton
Nature Link Resort

Cuyuna Lake cabin retreat. Fish, hike, bike trails, star gazing, mins to town.

Ironton
9.8 out of 10, Exceptional, (21)
"This was exactly what we were looking for! Very quiet and lovely view of the lake. A peaceful retreat. The cabin was clean and well appointed. A marvelous time getting away from all the hubbub. We enjoyed our stay."
United States
Rene
The price is NZ$686
includes taxes & fees
10 Nov - 11 Nov
Cuyuna Lake cabin retreat. Fish, hike, bike trails, star gazing, mins to town.

Lovely Tiny-House Cabin on Crosslake + Sauna + Bonfire + Kayak + Dock

Crosslake
10.0 out of 10, Exceptional, (1)
"Lovely place! We enjoyed our time there.If the bed was more comfortable, we would be more excited to come again!All in all, a wonderful place.Thank you!"
United States
Nathan L.
The price is NZ$558
includes taxes & fees
10 Nov - 11 Nov
Lovely Tiny-House Cabin on Crosslake + Sauna + Bonfire + Kayak + Dock

Bright Lakefront Getaway, steps from sandy Gull Lake beach

Nisswa
9.8 out of 10, Exceptional, (17)
"Close to the water. Great vacation. "
United States
Jeff Lorenson
The price is NZ$424
includes taxes & fees
10 Nov - 11 Nov
Bright Lakefront Getaway, steps from sandy Gull Lake beach

Don’t Miss This Cozy Rock Lake Fall Escape

Crosslake
8.6 out of 10, Excellent, (15)
"We enjoyed our long weekend stay. The home is spacious and has everything in the kitchen you might need. The wifi is slow, however. Not a deal breaker though. Hope to return again."
United States
Scott V.
The price is NZ$948
includes taxes & fees
10 Nov - 11 Nov
Don’t Miss This Cozy Rock Lake Fall Escape

Fishing cabin in the pines! 50 acres of lakeshore forest, & only YOU! Beauty.

Deerwood
9.0 out of 10, Wonderful, (9)
"The place was extremely private when we went and weren’t bothered by anyone which was our goal. We used a provided paddle boat and caught several award winning size bass and it took us very little skill. The largest was at sunrise at the dock, believe that or not! The home had great hot water and was a little outdated but absolutely perfect for a cabin getaway. There were a few bugs but hello were in the woods on a lake house on the water. I loved it and the kids did also. I had some additional...
United States
Jon W.
The price is NZ$680
includes taxes & fees
29 Nov - 30 Nov
Fishing cabin in the pines! 50 acres of lakeshore forest, & only YOU! Beauty.

New Lakefront |Pontoon|GameRoom|Summer Fun Vibes

Crosslake
10.0 out of 10, Exceptional, (8)
"They were great hosts and the place was such a beautifully designed home that had all the amenities and more. Would 100% recommend! "
United States
ReAnna G.
The price is NZ$1,307
includes taxes & fees
10 Nov - 11 Nov
New Lakefront |Pontoon|GameRoom|Summer Fun Vibes

In town, close to the trails, fully fenced in yard!

Crosby
10.0 out of 10, Exceptional, (13)
"A perfect place for a quick stay or a longer trip. Great amenities and super cozy!"
United States
Griffin C.
The price is NZ$660
includes taxes & fees
12 Nov - 13 Nov
In town, close to the trails, fully fenced in yard!

Winter, Spring, Summer or Fall, this place has it all! It's a great getaway spot

Breezy Point
9.4 out of 10, Exceptional, (20)
"This cabin was just as described and a great place to stay for a family wedding. The host was great (even when I called her in a panic from locking my family out just before the wedding!) and the cabin has everything you couldNeed for a quick getaway. "
United States
Joni P.
The price is NZ$405
includes taxes & fees
10 Nov - 11 Nov
Winter, Spring, Summer or Fall, this place has it all! It's a great getaway spot

NEW DESIGN~Summer on Chain of Lakes~Kings~Game Room

Crosslake
9.6 out of 10, Exceptional, (41)
"We had a great time during our stay. "
United States
Lisa M.
The price is NZ$1,496
includes taxes & fees
10 Nov - 11 Nov
NEW DESIGN~Summer on Chain of Lakes~Kings~Game Room

Wilderness Resort Villas

3.5 star property
Pequot Lakes
8.8 out of 10, Excellent, (102)
"Beautiful view, nice and peaceful. The pool table could use some work in villa 16. "
United States
Tim
The price is NZ$727
includes taxes & fees
21 Nov - 22 Nov
Wilderness Resort Villas

Lake Edward Retreat, Hot Tub, Game Rm, Mins to Nisswa

Nisswa
10.0 out of 10, Exceptional, (9)
" The house was perfect and so spacious. Macayla is so quick to respond!"
United States
Kasey G.
The price is NZ$924
includes taxes & fees
12 Nov - 13 Nov
Lake Edward Retreat, Hot Tub, Game Rm, Mins to Nisswa

Ultimate Cabin Retreat, Sauna, Firepit, Fireplace

Crosby
10.0 out of 10, Exceptional, (8)
"Absolutely loved our stay at the cabin. It was clean, everything we needed was provided. Enjoyed our weekend getaway. We’ll be back soon. "
United States
Isatu J.
The price is NZ$699
includes taxes & fees
16 Nov - 17 Nov
Ultimate Cabin Retreat, Sauna, Firepit, Fireplace

Lakeside Log Cabin w/Firepit, Dock, King Bed, Game Room, Scenic Relaxation

Baxter
10.0 out of 10, Exceptional, (14)
"This rental was amazing for our needs. We were in town for a family wedding, and the location was great. The view was very enjoyable. And the owners were very accommodating to our special needs. This was the best stocked VRBO we’ve ever stayed in! The coffee bar was so nice, the extra toiletries Were very thoughtful, and we had plenty of towels and bedding. I would recommend this to anyone who needs to stay in this area. "
United States
Rachel W.
The price is NZ$977
includes taxes & fees
11 Nov - 12 Nov
Lakeside Log Cabin w/Firepit, Dock, King Bed, Game Room, Scenic Relaxation

Summer oasis w/NEW HOT TUB overlooking Fawn Lake with private beach, SUPs/Kayaks

Crosslake
10.0 out of 10, Exceptional, (22)
"Nice private cabin to spend a weekend with friends at. We had a blast!"
United States
Mark R.
The price is NZ$1,462
includes taxes & fees
10 Nov - 11 Nov
Summer oasis w/NEW HOT TUB overlooking Fawn Lake with private beach, SUPs/Kayaks

Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling

Pequot Lakes
9.0 out of 10, Wonderful, (19)
"Cute little cottage! The kitchen is well equipped. The stairs to the upstairs bedrooms are very narrow and steep. Owner was quick to respond when we had a problem. We enjoyed our stay."
United States
Jennifer D.
The price is NZ$675
includes taxes & fees
10 Nov - 11 Nov
Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling

Log home nestled in tall pines near Norway Lake

Pine River
10.0 out of 10, Exceptional, (43)
"Property was clean and well laid out."
United States
Jesse R.
The price is NZ$728
includes taxes & fees
11 Nov - 12 Nov
Log home nestled in tall pines near Norway Lake

Ultimate Retreat: Cozy Cabin w/ Fireplace! Cuyuna MTB Access

Crosby
10.0 out of 10, Exceptional, (3)
"The cabin was amazing. The design and style was magnificent. Everything about the place was really thoughtful and planned out. It had everything a group needs to cook, eat, relax, and sleep. The direct access to the bike trail is great. I will stay here every time I come."
United States
Chris M.
The price is NZ$699
includes taxes & fees
23 Nov - 24 Nov
Ultimate Retreat: Cozy Cabin w/ Fireplace! Cuyuna MTB Access
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ossipee Hotel Reviews

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 favorite 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 depends 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 per night. Entering your travel dates in the search wizard you might find 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 holiday rentals 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. Ossipee is known for its lake views.

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

Eagle Pines: Rare, Beautiful North Shore of Gull Lake: This holiday home rental outside of Ossipee is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 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 will I find in Ossipee?

Choose from 6 Expedia holiday rentals in Ossipee for a memorable holiday.

What can I see and do in Ossipee?

Lake Edward and Mississippi River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Bass Lake and Upper Mission Lake.

What are holiday rentals like in Ossipee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ossipee. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family gatherings.