Ossipee Holiday Rentals

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Holiday Rentals in Ossipee

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

10.0 out of 10, Exceptional, (7)
"Great location, beautiful house , we were a bit upset that the outside hot tub was not available even though it was listed as part of the amenities."
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

10.0 out of 10, Exceptional, (165)
"Out 9th year and still a great stay. Owners, house, entire property, all top notch. Cant wait for year 10. "
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

Cozy Retreat near Ossipee Lake, sleeps 8, pet friendly!

9.8 out of 10, Exceptional, (17)
"Great spot, rural but with just the right amenities not too far. Bonus that the local (walking distance) lake was frozen over for some nice walks"
Cozy Retreat near Ossipee Lake, sleeps 8, pet friendly!

Close to ski areas, Prep Schools, walking to shops, dining, hiking, dog friendly

10.0 out of 10, Exceptional, (167)
"The cottage is absolutely perfect! Convenient location, cozy and so well done inside. Thoughtful touches everywhere. Such a treat to stay here. Welcoming and communicative host was icing on the cake!"
Close to ski areas, Prep Schools, walking to shops, dining, hiking, dog friendly

Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

9.8 out of 10, Exceptional, (93)
"Had an amazing stay. Cabin was exactly as described and host was excellent in communicating and making sure we had everything we needed (including snow removal etc) Would stay again!!"
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

9.8 out of 10, Exceptional, (152)
"Had a great time on family ski trip. Good location. Owner was great to work with. Nice and clean place. Kids and parents enjoyed. Owner goes out of his way to make it nice, comfortable and willing to address any concerns. "
The price is AU$888
includes taxes & fees
27 Feb - 28 Feb
Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room

Grand Blanc Mountain Home

9.8 out of 10, Exceptional, (91)
"From the very first trip. To now our 4th visit. Our closest friends and family have rented this home and every time it never disappoints. If you are looking to be off the grid and have the amenities of a hotel, but also be close to a major town if needing something. Look no further. This is the home you should rent. The best!"
Grand Blanc Mountain Home

The view-Enjoy Lake Winni both on & off the water-outdoor enthusiasts dream

2.5 star property
The view-Enjoy Lake Winni both on & off the water-outdoor enthusiasts dream

Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

9.6 out of 10, Exceptional, (133)
"We really enjoyed our stay. The condo was comfortable, clean, had everything you needed and was in a great location. We enjoyed walking across the street to the lake and up the hill to go the concert next door. We were also a short drive from Weirs Beach. We had great communication and hope to stay there again."
Stay at Gilford Resort/Ski Gunstock/ 10 min. Drive to Gunstock

Deck For Entertaining: Belmont Group Getaway

9.2 out of 10, Wonderful, (69)
"Great house. Everything was as we hoped. "
Deck For Entertaining: Belmont Group Getaway

Chalets Huttopia White Mountains

2.0 star property
9.8 out of 10, Exceptional, (11)
"Was amazing share a great memories with family there."
The price is AU$315
includes taxes & fees
2 Mar - 3 Mar
Chalets Huttopia White Mountains

Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

10.0 out of 10, Exceptional, (50)
"We were a group of 10 adults from several states (some friends, some family) celebrating a milestone birthday. Brian’s house fit the bill perfectly for our group. While we stayed during winter, we enjoyed the great views across the frozen lake and many of the great activities at the house (pool, ping pong, Nintendo) We spent much of our time cooking together and just visiting with each other. The kitchen was nicely stocked and there was the perfect amount of room for our group to dine...
Ultimate Lakefront Vacation Home for Rent - Lake Winnipesaukee - Amazing Sunsets

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (28)
"The property was very nice and clean. We enjoyed our stay very much!"
The price is AU$683
includes taxes & fees
16 Mar - 17 Mar
Cozy, Pet-Friendly Escape Near Lake & Mountains

Family Friendly Rustic Newly Renovated Cabin Abutting The White Lake State Park.

9.6 out of 10, Exceptional, (245)
"House and location were great for us to sightsee the area. Would rent again if coming up this way again. "
Family Friendly Rustic Newly Renovated Cabin Abutting The White Lake State Park.

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

9.8 out of 10, Exceptional, (78)
"We had a great time! Very Cozy home, perfect for a weekend away in the mountains. Easy access to the center of town with lots to do in the area. The apartment was beautifully decorated, very clean, and had everything we needed and then some. Marianne was available for any questions and was very thoughtful. Great spot to venture out from to explore. "
The price is AU$383
includes taxes & fees
23 Feb - 24 Feb
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Secluded Cabin on 400 Acres: Swim, Hike, Fish, Relax, PLAY!

10.0 out of 10, Exceptional, (110)
"Loved it"
Secluded Cabin on 400 Acres: Swim, Hike, Fish, Relax, PLAY!

New Lakefront Home sleeps 14 with dock.

8.8 out of 10, Excellent, (61)
"Location is very convenient - grocery within a 10 min ride, easy access to the Lake, dining, and popular Winnipesaukee villages around the lake. The amenities were generous - including towels and linens at the location, travel shampoo/condition/soaps available, fully stocked kitchen with dish soap and other kitchen tools available. The kitchen is tight and the central artery of the house, which made it difficult with 12 people. I'd recommend bringing a mattress pad or something for the pull...
New Lakefront Home sleeps 14 with dock.

Lake Winnipesaukee, Weirs Beach, Funspot, Gunstock

10.0 out of 10, Exceptional, (47)
"We had an amazing experience and would gladly come back in the future!"
Lake Winnipesaukee, Weirs Beach, Funspot, Gunstock

Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

6.8 out of 10, (9)
"I didn’t look close at the on-line pics so at first arrival I had concerns. It’s a charming older style lake house that could use a bit of pampering but it was very clean and comfortable for our group of 8. The host and management company were great and easy to communicate with. We came up for our daughter’s wedding and we all had a very nice weekend. Thank you"
Secluded, dog-friendly home with screened porch, firepit, fireplace & W/D

Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach

9.4 out of 10, Exceptional, (76)
"We had a lovely stay! The house was comfortable and cozy. A few upgrades would make this a five-star stay, otherwise it was perfect for our family. "
Dog-friendly A-frame with firepit, fireplace, AC, & kayaks - walk to the beach
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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Other types of properties in Ossipee you may be interested in

Green Granite Inn, Ascend Hotel Collection

2.5 star property
7.0 out of 10, Good, (1183)
"Pros: Overall, we enjoyed our stay and the king suite was much larger than expected. It was a great location, right in the heart of the outlet shopping and great restaurants. The indoor pool and hot tub were nice but could have used a better cleaning. Cons: It was outdated, one tv was not working properly, the tub (jacuzzi) was very hard to get in and out of and the water was just warm on the hottest setting, and the free breakfast was not good at all; eggs tasted like they were made from...
The price is AU$100
includes taxes & fees
23 Mar - 24 Mar
Green Granite Inn, Ascend Hotel Collection

Fireside Inn & Suites Gilford

2.5 star property
8.8 out of 10, Excellent, (734)
"Excellent location for activities, for any season. "
The price is AU$244
includes taxes & fees
23 Feb - 24 Feb
Fireside Inn & Suites Gilford

Mill Falls Resort Collection at the Lake

3.0 star property
8.2 out of 10, Very good, (649)
"Excellent hotel. Loved the pool and the fact that they have 4 EV chargers located right next to the hotel. Very much appreciated having the chargers on the property. Will certainly be staying there again. "
The price is AU$258
includes taxes & fees
23 Feb - 24 Feb
Mill Falls Resort Collection at the Lake
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.

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?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Ossipee is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Funspot Family Fun Center, or get outside and enjoy nature at Ossipee Lake Trail. In the wider area, you’ll find Lake Wentworth and Allen Albee Beach.

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.