Ossipee Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Ossipee holiday rentals

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, (84 reviews)
"We had our kids wedding here and the whole stay was enjoyable and relaxing it made for a very memorable day in our kids life together."
United States
Jeffrey
The price is HK$2,061
HK$2,390 total
includes taxes & fees
22 Jun - 23 Jun
Nature Link Resort
Fireplace

The Point - On Gull Lake

The Point - On Gull Lake
3.5 star property
Brainerd
9.4 out of 10, Exceptional, (3 reviews)
"Excellent price"
United States
Lisa
The price is HK$2,860
HK$4,293 total
includes taxes & fees
4 Jun - 5 Jun
The Point - On Gull Lake
Interior

Private Beach: Lakefront Escape in Brainerd!

Private Beach: Lakefront Escape in Brainerd!
3.0 star property
Brainerd
10.0 out of 10, Exceptional, (1 review)
"Clean "
United States
Derek
The price is HK$2,398
HK$6,203 total
includes taxes & fees
21 Jun - 22 Jun
Private Beach: Lakefront Escape in Brainerd!
Exterior

Step Outside & You're at the Lake | Beach Access & Boat Rentals Available

Step Outside & You're at the Lake | Beach Access & Boat Rentals Available
Nisswa
10.0 out of 10, Exceptional, (20 reviews)
"Perfect location for proximity to restaurants, outdoor activities, and lakeside fun. We will definitively be back."
United States
Susan
Step Outside & You're at the Lake | Beach Access & Boat Rentals Available
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.
Eagle`s Nest - Main House
Fridge, microwave, oven, stovetop

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

NEW DESIGN~Summer on Chain of Lakes~Kings~Game Room
Crosslake
9.6 out of 10, Exceptional, (43 reviews)
"Wonderful property with lots of space and amenities to have a good time. Responsive host, too!"
United States
Andrea M.
The price is HK$4,516
HK$10,335 total
includes taxes & fees
2 Jun - 3 Jun
NEW DESIGN~Summer on Chain of Lakes~Kings~Game Room
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, (27 reviews)
"Such a beautiful and peaceful place to get away. The host was very welcoming and super easy to work with. The christmas decorations made the place so joyous and festive."
United States
Jon L.
The price is HK$2,992
HK$7,603 total
includes taxes & fees
8 Jun - 9 Jun
Summer oasis w/NEW HOT TUB overlooking Fawn Lake with private beach, SUPs/Kayaks
Outdoor spa tub

NEW - The Boardwalk on North Long Lake Brainerd with Hot Tub, Pet-Friendly

NEW - The Boardwalk on North Long Lake Brainerd with Hot Tub, Pet-Friendly
Brainerd
9.8 out of 10, Exceptional, (39 reviews)
"The house was beautiful, clean, had everything we needed. We appreciated the stair gates, and the hot tub was used alot!"
United States
Richelle R.
NEW - The Boardwalk on North Long Lake Brainerd with Hot Tub, Pet-Friendly
Terrace/patio

Ultimate Cabin Retreat, Sauna, Firepit, Fireplace

Ultimate Cabin Retreat, Sauna, Firepit, Fireplace
Crosby
10.0 out of 10, Exceptional, (8 reviews)
"Great place, excellent location"
United States
MTB 7.
The price is HK$2,625
HK$4,140 total
includes taxes & fees
24 Jun - 25 Jun
Ultimate Cabin Retreat, Sauna, Firepit, Fireplace
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)
"Perfect for our reunion of friends and family who were staying in Brainerd Lakes for golf trip "
United States
Jacob A.
The price is HK$3,082
HK$7,718 total
includes taxes & fees
10 Jun - 11 Jun
New Lakefront |Pontoon|GameRoom|Summer Fun Vibes
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$2,625
HK$4,022 total
includes taxes & fees
7 Jun - 8 Jun
Ultimate Retreat: Cozy Cabin w/ Fireplace! Cuyuna MTB Access
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
9.4 out of 10, Exceptional, (26 reviews)
"Host was great. "
United States
Eric S.
The price is HK$1,213
HK$2,161 total
includes taxes & fees
2 Jun - 3 Jun
Winter, Spring, Summer or Fall, this place has it all! In Breezy Point Resort
Interior

16 Mi to Mount Ski Gull: Pequot Lakes Cabin

16 Mi to Mount Ski Gull: Pequot Lakes Cabin
3.0 star property
Pequot Lakes
The price is HK$956
HK$3,471 total
includes taxes & fees
3 Jun - 4 Jun
16 Mi to Mount Ski Gull: Pequot Lakes Cabin
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
9.6 out of 10, Exceptional, (25 reviews)
"Location and beautiful vista!"
United States
Chuck B.
The price is HK$1,763
HK$3,753 total
includes taxes & fees
2 Jun - 3 Jun
Cuyuna Lake cabin retreat. Fish, hike, bike trails, star gazing, mins to town.
Exterior

6000 Sq Feet w/Year Around Indoor Pool-King Beds

6000 Sq Feet w/Year Around Indoor Pool-King Beds
Crosslake
9.4 out of 10, Exceptional, (71 reviews)
"Great place"
United States
Tad
The price is HK$4,988
HK$13,566 total
includes taxes & fees
14 Jun - 15 Jun
6000 Sq Feet w/Year Around Indoor Pool-King Beds
Interior

ENJOY this New Construction! Private! Rustic! Mollie Lake Cabin! No SMOKING/PETS

ENJOY this New Construction! Private! Rustic! Mollie Lake Cabin! No SMOKING/PETS
Nisswa
10.0 out of 10, Exceptional, (249 reviews)
"Second time renting this cabin! We had a wonderful time hanging out with family. Layout of cabin is great for sleeping and cooking areas with nice big table to gather at. Great location to area restaurants and shopping also! Heated floors are awesome! Thank you for a great stay!"
United States
Jill S.
The price is HK$1,371
HK$2,886 total
includes taxes & fees
28 Jun - 29 Jun
ENJOY this New Construction! Private! Rustic! Mollie Lake Cabin! No SMOKING/PETS
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, (45 reviews)
"Awesome cabin!"
United States
Dean G.
The price is HK$2,077
HK$3,753 total
includes taxes & fees
1 Jul - 2 Jul
Log home nestled in tall pines near Norway Lake
Exterior

New! Tiny House Couples Retreat, Outdoor Shower

New! Tiny House Couples Retreat, Outdoor Shower
Ironton
10.0 out of 10, Exceptional, (7 reviews)
"Great place"
United States
Jorge R.
The price is HK$2,312
HK$3,417 total
includes taxes & fees
11 Jun - 12 Jun
New! Tiny House Couples Retreat, Outdoor Shower
Smart TV, fireplace, books, computer monitors

Sunset Serenity on Kego Lake: Lakefront, Private, Sauna, Fishing, Fully Stocked!

Sunset Serenity on Kego Lake: Lakefront, Private, Sauna, Fishing, Fully Stocked!
Fifty Lakes
The price is HK$1,664
HK$3,302 total
includes taxes & fees
8 Jun - 9 Jun
Sunset Serenity on Kego Lake: Lakefront, Private, Sauna, Fishing, Fully Stocked!
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

AmericInn by Wyndham Baxter Brainerd

AmericInn by Wyndham Baxter Brainerd

10/10 Excellent
"Front desk member was pleasant and greeted me with a smile. Housekeeping staff did an amazing job when requesting a later clean time for my room when staying multiple nights. A very nice variety of breakfast items to choose from (eggs, meat, biscuits, gravy, cereal, muffins/bread, pancakes, waffles, yogurt, milk, juice, and coffee/tea). Hotel is convenient walking distance to grocery/liquor store and great sushi/ramen restaurant."
Rachelle 4-night trip
Posted 3 hours ago
AmericInn by Wyndham Baxter Brainerd

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

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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?

6000 Sq Feet w/Year Around Indoor Pool-King Beds: 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 6 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 balcony, a garden and a pool table so that you can immerse yourself in your holiday.

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.