A boat on a calm lake at sunset with mountains in the background.

Search Holiday Homes in Ossipee

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Ossipee holiday homes

A deck with a view of a frozen lake and surrounding trees.

1. 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, (36 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 £227
includes taxes & fees
20 Nov - 21 Nov
A little slice of paradise, in all 4 seasons. Private beach, Dock and Sunsets!!
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, (16 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 £338
includes taxes & fees
29 Oct - 30 Oct
Cozy Tuftonboro Escape: Steps to Private Beaches!
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

3. Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...

Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
Alton
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay at the cozy cottage! The porch is very comfy and has great light. The beds were also very comfortable and kitchen was well stocked."
United States
Rebecca K.
The price is £313
includes taxes & fees
29 Oct - 30 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A living room with a stone fireplace, a ceiling fan, and a large window.

4. Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8

Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
Gilford
10.0 out of 10, Exceptional, (1 review)
"Home was clean Host was easy to communicate with"
United States
Robert L.
The price is £314
includes taxes & fees
2 Nov - 3 Nov
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
A large building with multiple sections, surrounded by snow-covered ground and trees, with a lake and mountains in the background.

5. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is £187
includes taxes & fees
29 Oct - 30 Oct
Cedar Lodge Room 2 Queen Beds & Private Balcony
Living area

6. Lotus Spa, your home away from home

Lotus Spa, your home away from home
Acton
10.0 out of 10, Exceptional, (63 reviews)
"We loved staying at the Lotus. Every detail exceeded our expectations."
United States
Kim M.
The price is £256
includes taxes & fees
9 Nov - 10 Nov
Lotus Spa, your home away from home
A sauna with wooden walls and benches, a central ventilation system, and a ceiling light.

7. Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
New Durham
9.0 out of 10, Wonderful, (4 reviews)
"Great location in the woods! House was roomy and very comfortable..Host was very accommodating and communicated promptly and thoroughly. Lots of beds for the family!"
United States
Mary T.
The price is £425
includes taxes & fees
29 Oct - 30 Oct
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
A loft-style bedroom with a sloped ceiling, a ceiling fan, a bed, a desk, and a kitchenette.

8. Peaceful Barn Loft near Sebago Lake and Conway, NH

Peaceful Barn Loft near Sebago Lake and Conway, NH
Hiram
The price is £154
includes taxes & fees
29 Oct - 30 Oct
Peaceful Barn Loft near Sebago Lake and Conway, NH
A cozy kitchen with wooden flooring, a brick wall, and a blue stove. There are bar stools and a small table with chairs.

9. Welcome to the Z E N

Welcome to the Z E N
Acton
9.6 out of 10, Exceptional, (20 reviews)
"This place was the perfect retreat!"
United States
Jennifer B.
The price is £274
includes taxes & fees
2 Nov - 3 Nov
Welcome to the Z E N
A two-story house with a covered porch and a small deck.

10. Meredith Bay - Brand New 1st Floor Apartment In Private Home

Meredith Bay - Brand New 1st Floor Apartment In Private Home
Meredith
10.0 out of 10, Exceptional, (53 reviews)
"The apartment was very comfortable and just as pictured. We had a wonderful stay! It’s a great location for walking in Meredith and an easy drive to ski at Gunstock. "
United States
Karen O.
The price is £220
includes taxes & fees
29 Oct - 30 Oct
Meredith Bay - Brand New 1st Floor Apartment In Private Home
A lakeside view from a wooden deck with an American flag, surrounded by trees and a clear sky.

11. Waterfront w/ Prvt Dock & Firepit | Sleeps 8

Waterfront w/ Prvt Dock & Firepit | Sleeps 8
Acton
9.0 out of 10, Wonderful, (27 reviews)
"This is our first experience, so we have nothing to compare with, but we liked it very much."
United States
edward k.
The price is £546
includes taxes & fees
31 Oct - 1 Nov
Waterfront w/ Prvt Dock & Firepit | Sleeps 8
A lakeside property with a dock, a boat, and a house with a deck.

12. Stay in Venice our Modern Steps from the Lake with Dock!

Stay in Venice our Modern Steps from the Lake with Dock!
Alton
10.0 out of 10, Exceptional, (9 reviews)
"Great location on the lake!"
United States
Stephanie H.
The price is £272
includes taxes & fees
3 Nov - 4 Nov
Stay in Venice our Modern Steps from the Lake with Dock!
A cozy living room with a large flat-screen TV, wooden ceiling beams, a leather sofa, and a dining area with a table and chairs.

13. Hot Tub,King Bed,Dogs w/Pequawket Beach Access!

Hot Tub,King Bed,Dogs w/Pequawket Beach Access!
Conway
9.4 out of 10, Exceptional, (3 reviews)
"Clean house with a very responsive host. The bathroom is tiny. Fine for one night, but no longer for three women."
United States
Susan L.
The price is £347
includes taxes & fees
1 Nov - 2 Nov
Hot Tub,King Bed,Dogs w/Pequawket Beach Access!
A cozy living room with a fireplace, leather furniture, and a large TV.

14. Luxe Lodge in the Woods! With Sauna & Hot tub

Luxe Lodge in the Woods! With Sauna & Hot tub
Conway
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful property with everything a family with young kids needs. Especially love the hottub and air hockey table!"
United States
Anonymous traveller
The price is £382
includes taxes & fees
2 Nov - 3 Nov
Luxe Lodge in the Woods! With Sauna & Hot tub
A hot tub in front of a wooden cabin with a deck, surrounded by trees.

15. Secluded White Mtns Retreat • Hot Tub • Sleeps 10 • Pet Friendly

Secluded White Mtns Retreat • Hot Tub • Sleeps 10 • Pet Friendly
Albany
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful and peaceful trip to this location. The house is beautiful "
United States
Jillian H.
The price is £546
includes taxes & fees
21 Nov - 22 Nov
Secluded White Mtns Retreat • Hot Tub • Sleeps 10 • Pet Friendly
A rustic kitchen with wooden cabinets, a large window, and a variety of kitchen items on the counter.

16. Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
Gilford
10.0 out of 10, Exceptional, (3 reviews)
"We had a great time at the Wagner Ranch. The bedrooms were comfy and the kitchen had all necessary items. Definitely will stay there again. The hosts were Great!"
United States
dave b.
The price is £414
includes taxes & fees
29 Oct - 30 Oct
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
A spacious kitchen with a large island, a dining area with a view, and a fireplace.

17. Mtn View | Outdoor hot tub + fireplace | 10+ Guest

Mtn View | Outdoor hot tub + fireplace | 10+ Guest
Conway
9.6 out of 10, Exceptional, (40 reviews)
"We had a great stay at this property for two nights. The check-in process was seamless, and Jeremy was a great host with excellent communication throughout our stay. The location was perfect, only about a 10-minute drive from North Conway while still being in a nice, quiet area. The house was very clean, spacious, and comfortable. There were six beds available along with large couches, so there was plenty of room for everyone. The hot tub was also a great addition and made the stay even more...
United States
Shane
The price is £411
includes taxes & fees
29 Oct - 30 Oct
Mtn View | Outdoor hot tub + fireplace | 10+ Guest
A bedroom with a sloped ceiling, a wooden bed, and a brick accent wall.

18. New Lakefront Home sleeps 14 with dock.

New Lakefront Home sleeps 14 with dock.
Alton
8.6 out of 10, Excellent, (76 reviews)
"Plenty of parking, easy check in, plenty of sleeping areas and sitting areas. "
United States
Caroline M.
The price is £577
includes taxes & fees
2 Nov - 3 Nov
New Lakefront Home sleeps 14 with dock.
A beach with sand, trees, and a boat in the background.

19. 5-Acres, 1 Min to Gunstock, Beautiful Mtn Views, Hot Tub, Game Room + More!

5-Acres, 1 Min to Gunstock, Beautiful Mtn Views, Hot Tub, Game Room + More!
Gilford
9.8 out of 10, Exceptional, (26 reviews)
"Great spot for the week of the 4th!"
United States
Griffin R.
The price is £616
includes taxes & fees
29 Oct - 30 Oct
5-Acres, 1 Min to Gunstock, Beautiful Mtn Views, Hot Tub, Game Room + More!
A historic building with a large tree in front, a reflection pool, and mountains in the background.

20. River Access, hot tub, dogs!

River Access, hot tub, dogs!
Conway
9.0 out of 10, Wonderful, (2 reviews)
"great property. great stay. host was great to work with."
United States
Morgan B.
The price is £372
includes taxes & fees
4 Nov - 5 Nov
River Access, hot tub, dogs!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossipee Hotel Reviews

Home2 Suites by Hilton North Conway

Home2 Suites by Hilton North Conway

8/10 Good
"Knowledgeable staff. Nice spacious room and bathroom. Bathroom was kind of dark outside of the tub area. Great breakfast."
Christina 1-night trip
Posted 6 hours ago
Home2 Suites by Hilton North Conway

Find out more about Ossipee

Ossipee Holiday Homes information

Number of reviews
287
Accommodation
924 Holiday Homes
Lowest Price
£154
Highest Price
£616