Ossipee Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Ossipee holiday rentals

Smart TV, fireplace, books

Cozy cabin w hot tub & fireplace, near Nisswa/crosslake

Cozy cabin w hot tub & fireplace, near Nisswa/crosslake
Merrifield
10.0 out of 10, Exceptional, (14 reviews)
"The property is beautiful and cozy."
United States
Amy O.
The price is HK$1,548
HK$3,577 total
includes taxes & fees
9 Mar - 10 Mar
Cozy cabin w hot tub & fireplace, near Nisswa/crosslake
Premium bedding, pillow-top beds, blackout curtains, free WiFi

Nature Link Resort

Nature Link Resort
3.0 star property
Nisswa
9.8 out of 10, Exceptional, (74 reviews)
"The room was so comfortable! We loved the fireplace, the bed and the huge bathroom. The view and the windows were beautiful!"
United States
Angela
Nature Link Resort
TV, fireplace, video games, DVD player

Crosslake Winter Cabin | Rock Lake Ice Fishing

Crosslake Winter Cabin | Rock Lake Ice Fishing
Crosslake
8.4 out of 10, Very good, (17 reviews)
"Amazing!"
United States
Ty J.
The price is HK$718
HK$3,901 total
includes taxes & fees
1 Mar - 2 Mar
Crosslake Winter Cabin | Rock Lake Ice Fishing
Marina

Winter, Spring, Summer or Fall, this place has it all! In Breezy Point Resort

Winter, Spring, Summer or Fall, this place has it all! In Breezy Point Resort
Breezy Point
9.6 out of 10, Exceptional, (24 reviews)
"Great communication, very helpful, very clean!"
United States
Kristen C.
The price is HK$1,056
HK$1,780 total
includes taxes & fees
1 Mar - 2 Mar
Winter, Spring, Summer or Fall, this place has it all! In Breezy Point Resort
Outdoor dining

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

Cuyuna Lake cabin retreat. Fish, hike, bike trails, star gazing, mins to town.
Ironton
9.8 out of 10, Exceptional, (22 reviews)
"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 HK$1,297
HK$3,164 total
includes taxes & fees
3 Mar - 4 Mar
Cuyuna Lake cabin retreat. Fish, hike, bike trails, star gazing, mins to town.
Outdoor spa tub

Centrally located "Perch Lake Bungalow" w/Hot-tub!

Centrally located "Perch Lake Bungalow" w/Hot-tub!
Baxter
10.0 out of 10, Exceptional, (10 reviews)
"Everything was great"
United States
Tou X.
The price is HK$958
HK$2,087 total
includes taxes & fees
8 Mar - 9 Mar
Centrally located "Perch Lake Bungalow" w/Hot-tub!
Property grounds

Hidden Gem on Gull Lake w/ large playground for families

Hidden Gem on Gull Lake w/ large playground for families
Nisswa
9.8 out of 10, Exceptional, (35 reviews)
"Customer service was great, location, beach and water front great, family friendly. "
United States
Kelly N.
The price is HK$1,076
HK$1,656 total
includes taxes & fees
5 Mar - 6 Mar
Hidden Gem on Gull Lake w/ large playground for families
Exterior detail

Lake View, Speakeasy, Sauna, Arcade, Ping Pong, Kayaks, Disc Golf, Poker, B-Ball

Lake View, Speakeasy, Sauna, Arcade, Ping Pong, Kayaks, Disc Golf, Poker, B-Ball
Crosby
10.0 out of 10, Exceptional, (2 reviews)
"Great location, beautiful home, fun stay, good value"
United States
Northwoods C.
The price is HK$1,021
HK$3,658 total
includes taxes & fees
1 Mar - 2 Mar
Lake View, Speakeasy, Sauna, Arcade, Ping Pong, Kayaks, Disc Golf, Poker, B-Ball
Interior

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

In town, close to the trails, fully fenced in yard!
Crosby
10.0 out of 10, Exceptional, (16 reviews)
"The place was clean, spacious and nicely located. Would stay here again!"
United States
Cheryl K.
The price is HK$773
HK$2,761 total
includes taxes & fees
2 Mar - 3 Mar
In town, close to the trails, fully fenced in yard!
Terrace/patio

Ultimate Cabin Retreat, Sauna, Firepit, Fireplace

Ultimate Cabin Retreat, Sauna, Firepit, Fireplace
Crosby
10.0 out of 10, Exceptional, (8 reviews)
"Was a great stay for me and my wife would definitely stay here again. Close to the bike trail and walking distance to up town."
United States
Nathan L.
The price is HK$1,759
HK$3,006 total
includes taxes & fees
8 Mar - 9 Mar
Ultimate Cabin Retreat, Sauna, Firepit, Fireplace
Exterior

Trout Lake Cabin Retreat

Trout Lake Cabin Retreat
Crosslake
The price is HK$1,173
HK$5,264 total
includes taxes & fees
10 Mar - 11 Mar
Trout Lake Cabin Retreat
Exterior

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

Summer oasis w/NEW HOT TUB overlooking Fawn Lake with private beach, SUPs/Kayaks
Crosslake
10.0 out of 10, Exceptional, (25 reviews)
"We had a girls trip and absolutely loved this cabin! Cabin was exactly as described and the owners were very responsive and helpful. We would definitely stay here again. Hot tub was great since it was cold while we were there!"
United States
Chelsea B.
The price is HK$1,720
HK$5,849 total
includes taxes & fees
1 Mar - 2 Mar
Summer oasis w/NEW HOT TUB overlooking Fawn Lake with private beach, SUPs/Kayaks
Interior

Log home nestled in tall pines near Norway Lake

Log home nestled in tall pines near Norway Lake
Pine River
10.0 out of 10, Exceptional, (44 reviews)
"Awesome cabin!"
United States
Dean G.
The price is HK$1,642
HK$3,216 total
includes taxes & fees
1 Mar - 2 Mar
Log home nestled in tall pines near Norway Lake
Smart TV, video games, table football, ping pong

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

Lakeside Log Cabin w/Firepit, Dock, King Bed, Game Room, Scenic Relaxation
Baxter
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay. Very cozy and clean and within close range of all Brainerd has to offer."
United States
Dan C.
The price is HK$1,290
HK$4,386 total
includes taxes & fees
4 Mar - 5 Mar
Lakeside Log Cabin w/Firepit, Dock, King Bed, Game Room, Scenic Relaxation
Smart TV, fireplace, DVD player, books

New Lakefront |Pontoon|GameRoom|Summer Fun Vibes

New Lakefront |Pontoon|GameRoom|Summer Fun Vibes
Crosslake
10.0 out of 10, Exceptional, (8 reviews)
"Very fun place to stay with grocery stores nearby! Beautiful scenery, and the gameroom was a big hit! Host was very welcoming and easy to chat with! "
United States
Aigner V.
The price is HK$1,720
HK$5,849 total
includes taxes & fees
1 Mar - 2 Mar
New Lakefront |Pontoon|GameRoom|Summer Fun Vibes
Property grounds

Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling

Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling
Pequot Lakes
8.8 out of 10, Excellent, (20 reviews)
"Our stay was perfect! Plenty of necessities to get us through a wonderful week in Pequot Lakes. I highly recommend."
United States
Michael W.
The price is HK$1,309
HK$3,051 total
includes taxes & fees
12 Mar - 13 Mar
Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling
Marina

Nisswa Hotel & Suites – Round Lake King Patio Suite with Full Kitchen

Nisswa Hotel & Suites – Round Lake King Patio Suite with Full Kitchen
Nisswa
The price is HK$542
HK$984 total
includes taxes & fees
2 Mar - 3 Mar
Nisswa Hotel & Suites – Round Lake King Patio Suite with Full Kitchen
Smart TV, fireplace, ping pong, books

Eagle`s Nest - Main House

Eagle`s Nest - Main House
Brainerd
10.0 out of 10, Exceptional, (4 reviews)
"Well equipped and maintained property in a very nice location. "
United States
Harvey E.
The price is HK$2,737
HK$7,262 total
includes taxes & fees
3 Mar - 4 Mar
Eagle`s Nest - Main House
Interior

The Painted Turtle: Lakefront, Hot Tub, Sauna, Theater, Game Room, Playset

The Painted Turtle: Lakefront, Hot Tub, Sauna, Theater, Game Room, Playset
Nisswa
10.0 out of 10, Exceptional, (2 reviews)
"Very communicative host, very clean, beautiful and inviting cabin and everything was above an average stay from the towel softness and quality to the cozy bedding and pillows and just all the extras on the property it’s truly an amazing stay and I would recommend to anyone and will hopefully get the chance to stay again soon! "
United States
Jenine T.
The price is HK$1,051
HK$4,159 total
includes taxes & fees
3 Mar - 4 Mar
The Painted Turtle: Lakefront, Hot Tub, Sauna, Theater, Game Room, Playset
Smart TV, fireplace

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

Ultimate Retreat: Cozy Cabin w/ Fireplace! Cuyuna MTB Access
Crosby
10.0 out of 10, Exceptional, (3 reviews)
"Had a great relaxing time"
United States
David V.
The price is HK$1,760
HK$3,075 total
includes taxes & fees
1 Mar - 2 Mar
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.
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

Nature Link Resort

Nature Link Resort

10/10 Excellent
"Beautiful accommodations."
Garrett 2-night trip
Posted 2 days ago
Nature Link Resort

Find out more about Ossipee

Search for holiday rentals in Ossipee on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossipee using one of the methods below:

  • View our selection of featured holiday rentals in Ossipee
  • Use the map to find apartments and other holiday homes in the Ossipee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ossipee while they last

Look no further and take a look at our great range of rental properties in Ossipee!

Explore a world of travel with Expedia

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?

Family Getaway on Two Private Lakes: This holiday home rental outside of Ossipee is located on a lake, 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. 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 Lower Mission Lake and Bass 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.