Search Vacation Homes in Ossipee

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Vacation Homes in Ossipee

Terrace/patio
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, (14)
"The place was clean, spacious and nicely located. Would stay here again!"
United States
Cheryl K.
$345 nightly
The price is $370
Dec 9 - Dec 10
Total with taxes and fees
In town, close to the trails, fully fenced in yard!
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)
"Great location, beautiful home, fun stay, good value"
United States
Northwoods C.
$460 nightly
The price is $493
Dec 7 - Dec 8
Total with taxes and fees
Lake View, Speakeasy, Sauna, Arcade, Ping Pong, Kayaks, Disc Golf, Poker, B-Ball
Exterior
Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling

Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling

Pequot Lakes
9.0 out of 10, Wonderful, (19)
"Our stay was perfect! Plenty of necessities to get us through a wonderful week in Pequot Lakes. I highly recommend."
United States
Michael W.
$353 nightly
The price is $379
Dec 7 - Dec 8
Total with taxes and fees
Cozy 3 Bedroom Bungalow near Lake, Fishing, Snowmobiling
Smart TV, video games, foosball, table tennis
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, (14)
"Great place to stay. Very cozy and clean and within close range of all Brainerd has to offer."
United States
Dan C.
$509 nightly
The price is $549
Dec 8 - Dec 9
Total with taxes and fees
Lakeside Log Cabin w/Firepit, Dock, King Bed, Game Room, Scenic Relaxation
5 bedrooms, iron/ironing board, free WiFi, bed sheets
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, (42)
"Very nice place to stay, there are a lot of steps. Plenty of bedrooms and space for everyone. "
United States
Jerry H.
$783 nightly
The price is $841
Dec 7 - Dec 8
Total with taxes and fees
NEW DESIGN~Summer on Chain of Lakes~Kings~Game Room
Interior
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)
"Had a great relaxing time"
United States
David V.
$366 nightly
The price is $393
Dec 8 - Dec 9
Total with taxes and fees
Ultimate Retreat: Cozy Cabin w/ Fireplace! Cuyuna MTB Access
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, (43)
"Lovely property."
United States
Vicki T.
$383 nightly
The price is $411
Dec 8 - Dec 9
Total with taxes and fees
Log home nestled in tall pines near Norway Lake
Fridge, microwave, oven, stovetop
Lakes-area vacation - walk to Pelican Lake, golfing, bars, restaurants and more!

Lakes-area vacation - walk to Pelican Lake, golfing, bars, restaurants and more!

Pequot Lakes
8.0 out of 10, Very Good, (1)
"Very nice accommodations. Kitchen had everything we needed including spices and plastic wrap... Inside clean."
United States
Pat B.
$477 nightly
The price is $512
Dec 31 - Jan 1, 2026
Total with taxes and fees
Lakes-area vacation - walk to Pelican Lake, golfing, bars, restaurants and more!
Dining
Life Is Good Lodge lakefront, private beach between Brainerd & Nisswa, game room

Life Is Good Lodge lakefront, private beach between Brainerd & Nisswa, game room

First Assessment
9.8 out of 10, Exceptional, (23)
"Great location. Kids loved the sandy beach."
United States
Sara W.
$817 nightly
The price is $858
Dec 8 - Dec 9
Total with taxes and fees
Life Is Good Lodge lakefront, private beach between Brainerd & Nisswa, game room
Smart TV, DVD player, books
Lakeside Escape | Water Fun, Cycling & More!

Lakeside Escape | Water Fun, Cycling & More!

Crosby
9.8 out of 10, Exceptional, (97)
"We had a great weekend with friends for a biking and relaxing weekend. Everything was great!"
United States
Tyler S.
$843 nightly
The price is $905
Dec 8 - Dec 9
Total with taxes and fees
Lakeside Escape | Water Fun, Cycling & More!
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

Grand View Lodge

Grand View Lodge

10/10 Excellent
"The staff was so friendly. Our room was spotless and really cute. We love the chairs outside. I had some work to do in the great room. It was cozy and nicely decorated. We had a blast in the restaurant and walking the campus. Overall amazing stay! "
Jill 2-night trip
Posted 2 days ago
Grand View Lodge

Find out more about Ossipee

Ossipee Vacation Homes information

Number of reviews
254
Accommodation
230 Vacation Homes
Lowest Price
$370
Highest Price
$905

Explore a world of travel with Expedia