Ossipee Holiday Rentals

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Check prices for these dates

Tonight
16 Jul - 17 Jul
Tomorrow
17 Jul - 18 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Ossipee

Waterfront Home w/ Dock & Fire Pit in Pine River
Relax in a serene outdoor setting surrounded by lush greenery and a tranquil body of water.

Waterfront Home w/ Dock & Fire Pit in Pine River

10.0 out of 10, Exceptional, (2)
"This was the best choice for us."
Waterfront Home w/ Dock & Fire Pit in Pine River
Charming 2-bedroom house with AC, WiFi in delightful Brainerd
Property grounds

Charming 2-bedroom house with AC, WiFi in delightful Brainerd

8.0 out of 10, Very good, (1)
"Ive stayed in a few houses and this one wasnt much different except all the extras she had! From dog toys and coffee to bath bombs and snacks...it was so generous (even though i didnt use most of it, i did enjoy the chocolate!)"
The price is HK$863
HK$1,264 total
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom house with AC, WiFi in delightful Brainerd
Rustic Lodge | Riverside | WiFi | Pets OK!
Two single beds with white linens, a flat-screen TV, and wardrobe with mirror.

Rustic Lodge | Riverside | WiFi | Pets OK!

10.0 out of 10, Exceptional, (1)
"The manager called to confirm our room number and door code- assured us she'd test the code to make sure it would work for us and glad she did. Rain was coming down when we arrived and we got in quickly! Room was very clean/updated, all guests were polite and staff is very friendly as well. Would recommend"
The price is HK$1,469
HK$1,841 total
includes taxes & fees
17 Jul - 18 Jul
Rustic Lodge | Riverside | WiFi | Pets OK!
Modern & cozy - sleeps 12! Right at Trailhead
Dining

Modern & cozy - sleeps 12! Right at Trailhead

10.0 out of 10, Exceptional, (12)
"We really enjoyed our stay, there was plenty of room for everyone. Kitchen had everything we needed. Beds and linens were super comfortable. We would love to come back in the summer, location is great for walking into town. Hosts were super responsive and accomodating. Will be back! "
The price is HK$2,056
HK$5,177 total
includes taxes & fees
20 Jul - 21 Jul
Modern & cozy - sleeps 12! Right at Trailhead
Biker's Paradise at Trailhead Lodge
TV, fireplace

Biker's Paradise at Trailhead Lodge

10.0 out of 10, Exceptional, (13)
"Already made our reservations for next year. The location and amenities were perfect. "
Biker's Paradise at Trailhead Lodge
In town, close to the trails, fully fenced in yard!
Relax on the outdoor patio with a comfortable seating area featuring two chairs and a small table.

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

10.0 out of 10, Exceptional, (7)
"A perfect place for a quick stay or a longer trip. Great amenities and super cozy!"
The price is HK$1,372
HK$3,614 total
includes taxes & fees
30 Jul - 31 Jul
In town, close to the trails, fully fenced in yard!
Lake House w/Hot Tub, Game Room, Fireplace & Beach
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and large windows offering views of the surrounding area.

Lake House w/Hot Tub, Game Room, Fireplace & Beach

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a fantastic time at the beautiful place!"
Lake House w/Hot Tub, Game Room, Fireplace & Beach
Log home nestled in tall pines near Norway Lake
Step into a cozy cabin with a rustic design, featuring a central staircase and natural charm.

Log home nestled in tall pines near Norway Lake

10.0 out of 10, Exceptional, (33)
"Clean with all the amenities you need. "
The price is HK$1,962
HK$3,616 total
includes taxes & fees
30 Jul - 31 Jul
Log home nestled in tall pines near Norway Lake
Stunning Cabin on Crooked Lake, MN
Cozy attic retreat with a wooden bed, bedside table, and window with blinds.

Stunning Cabin on Crooked Lake, MN

10.0 out of 10, Exceptional, (34)
"We enjoyed our family vacation, nice and quiet and room for everybody."
The price is HK$2,254
HK$4,898 total
includes taxes & fees
28 Jul - 29 Jul
Stunning Cabin on Crooked Lake, MN
New Lakefront |Pontoon|GameRoom|Summer Fun Vibes
Cozy cabin interior with a stone fireplace, wooden mantel, and a bench for relaxation.

New Lakefront |Pontoon|GameRoom|Summer Fun Vibes

10.0 out of 10, Exceptional, (1)
"Perfect for our reunion of friends and family who were staying in Brainerd Lakes for golf trip "
The price is HK$3,976
HK$8,315 total
includes taxes & fees
23 Jul - 24 Jul
New Lakefront |Pontoon|GameRoom|Summer Fun Vibes
NEW DESIGN~Summer on Chain of Lakes~Kings~Game Room
Cozy cabin with a dining area, kitchenette, and two beds.

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

9.6 out of 10, Exceptional, (37)
"Had a great time! The place was very spacious with a great layout. Lots of options for fun and great amenities overall. Very clean. Great communication with host. Would gladly stay again!"
NEW DESIGN~Summer on Chain of Lakes~Kings~Game Room
NEW! Gull Lake Retreat steps from shore, Pontoon Rentals, Sports Court
Fridge, microwave, oven, stovetop

NEW! Gull Lake Retreat steps from shore, Pontoon Rentals, Sports Court

10.0 out of 10, Exceptional, (3)
"Thank you for the place to stay for Thanksgiving. So convenient to get to and close to Brainerd and Nisswa."
The price is HK$4,843
HK$6,303 total
includes taxes & fees
20 Jul - 21 Jul
NEW! Gull Lake Retreat steps from shore, Pontoon Rentals, Sports Court
Gull Lake Interlachen Townhouse with Scenic Creek Views
Experience the contemporary design of this multi-story building with large windows, outdoor seating areas, and a well-maintained lawn.

Gull Lake Interlachen Townhouse with Scenic Creek Views

9.8 out of 10, Exceptional, (27)
"Comfortable rooms with nice linen. Great for adults looking for downtime. 5 minutes to nice restaurants in any direction. Property backs up to a stream connecting Gull and Round Lakes."
The price is HK$6,541
HK$8,379 total
includes taxes & fees
17 Jul - 18 Jul
Gull Lake Interlachen Townhouse with Scenic Creek Views
Popular Interlachen Condo with Relaxing Creek Views & steps away from Gull Lake
Enjoy waterfront views from the large windows of our cabins, offering a serene lakeside setting with access to water activities.

Popular Interlachen Condo with Relaxing Creek Views & steps away from Gull Lake

9.8 out of 10, Exceptional, (63)
"Very nice property. Great location. A few extra blankets would be nice. "
The price is HK$6,460
HK$8,284 total
includes taxes & fees
20 Jul - 21 Jul
Popular Interlachen Condo with Relaxing Creek Views & steps away from Gull Lake
Lower Whitefish Guest House Crosslake ~ Absolutely Beautiful Property!
Relax by the stone fireplace in a serene wooded setting, surrounded by Adirondack chairs.

Lower Whitefish Guest House Crosslake ~ Absolutely Beautiful Property!

9.8 out of 10, Exceptional, (158)
"Great place and great host!"
The price is HK$5,298
HK$8,098 total
includes taxes & fees
9 Aug - 10 Aug
Lower Whitefish Guest House Crosslake ~ Absolutely Beautiful Property!
NEW! Cozy Creekside Townhome Steps from Gull Lake Access
Interior

NEW! Cozy Creekside Townhome Steps from Gull Lake Access

The price is HK$4,762
HK$6,199 total
includes taxes & fees
17 Jul - 18 Jul
NEW! Cozy Creekside Townhome Steps from Gull Lake Access
Riverside Retreat | Pets OK! | WiFi | Fishing
Relax in a spacious room with a large bed, bedside table, and wall-mounted shelf.

Riverside Retreat | Pets OK! | WiFi | Fishing

The price is HK$1,607
HK$2,018 total
includes taxes & fees
17 Jul - 18 Jul
Riverside Retreat | Pets OK! | WiFi | Fishing
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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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?

Charming 2-bedroom house with AC, WiFi in delightful Brainerd: This holiday home rental outside of Ossipee is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities such as a stovetop and a microwave can make your holiday run smoothly.

How many holiday rentals will I find in Ossipee?

Choose from 8 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.