Ossipee Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Ossipee

*HIGH DEMAND* Sugar Sand Beach & Cozy Cabin That Sleeps 10 on Pelican Lake!
Fridge, microwave, oven, stovetop

*HIGH DEMAND* Sugar Sand Beach & Cozy Cabin That Sleeps 10 on Pelican Lake!

9.8 out of 10, Exceptional, (71)
"The property, cabin and lake were all great. We had a wonderful time!!"
*HIGH DEMAND* Sugar Sand Beach & Cozy Cabin That Sleeps 10 on Pelican Lake!
Nature Link Resort
1 bedroom, premium bedding, pillow-top beds, blackout curtains

Nature Link Resort

3.0 star property
9.6 out of 10, Exceptional, (58)
"Second stay on the property and we enjoyed it even more this go round"
Nature Link Resort
Oct weekend dates still open! Clean Cabin, lots of Amenities & Gull Chain Access
Outdoor dining

Oct weekend dates still open! Clean Cabin, lots of Amenities & Gull Chain Access

9.8 out of 10, Exceptional, (47)
"Safe for family & beautiful lake view"
The price is HK$1,576
HK$4,082 total
includes taxes & fees
5 Oct - 6 Oct
Oct weekend dates still open! Clean Cabin, lots of Amenities & Gull Chain Access
Vintage Cabin on Beautiful Lake O'brien - Includes Pontoon Boat
Exterior

Vintage Cabin on Beautiful Lake O'brien - Includes Pontoon Boat

10.0 out of 10, Exceptional, (172)
"Stunning views, beautiful accommodations and attentive owners. Thank you so much for a much needed, relaxing, peaceful get away!"
Vintage Cabin on Beautiful Lake O'brien - Includes Pontoon Boat
New Lake Home on Upper Cullen - volleyball, game room, sauna, and lots of trees!
Fridge, microwave, oven, stovetop

New Lake Home on Upper Cullen - volleyball, game room, sauna, and lots of trees!

10.0 out of 10, Exceptional, (8)
"Guys trip went good overall"
New Lake Home on Upper Cullen - volleyball, game room, sauna, and lots of trees!
Stunning 4 Bedroom Lake Home close to everything!!
Smart TV, fireplace, stereo

Stunning 4 Bedroom Lake Home close to everything!!

9.8 out of 10, Exceptional, (51)
"The house and property are beautiful and just as described in the listing. We were a group of 6 women in our 40s and the house and bedrooms were perfect for us to hang out and sleep comfortably. The outside areas are wonderful! The property manager was super responsive and helpful. We would definitely stay again! "
Stunning 4 Bedroom Lake Home close to everything!!
Modern Rustic Cabin-Includes Pontoon Boat & Sunsets on Fantastic Lakeside Porch!
Exterior

Modern Rustic Cabin-Includes Pontoon Boat & Sunsets on Fantastic Lakeside Porch!

10.0 out of 10, Exceptional, (158)
"The cabin was terrific for our multi-generational getaway. We loved the thoughtful design touches, the bedrooms with en-suite bathrooms, and the large bunk room in the lower floor. Having a private dock with our own pontoon boat was a big plus!"
Modern Rustic Cabin-Includes Pontoon Boat & Sunsets on Fantastic Lakeside Porch!
Elevate Your Stay!
Exterior

Elevate Your Stay!

10.0 out of 10, Exceptional, (84)
"Great place to stay. Spent the week riding bikes and walking. We love the Crosslake area."
Elevate Your Stay!
Classic Minnesota Cabin on Beautiful Lake O'Brien - Includes Pontoon Boat
TV, fireplace, DVD player

Classic Minnesota Cabin on Beautiful Lake O'Brien - Includes Pontoon Boat

10.0 out of 10, Exceptional, (318)
"Everything is top notch…from the pontoon to the sunroom to all of the cozy sitting areas, and oh those comfy beds and linens. Wonderful hosts as well!"
Classic Minnesota Cabin on Beautiful Lake O'Brien - Includes Pontoon Boat
Gull Lake Cabin + Bunkhouse with Sandy Beach & Pontoon/Jet Ski availability!
Beach

Gull Lake Cabin + Bunkhouse with Sandy Beach & Pontoon/Jet Ski availability!

10.0 out of 10, Exceptional, (4)
"We loved our stay here! Was in the perfect location and had everything we needed. Overall great experience! "
Gull Lake Cabin + Bunkhouse with Sandy Beach & Pontoon/Jet Ski availability!
Cozy cabin 25ft off the water! Near shopping, Restaurants, Attractions & Golf!
Interior

Cozy cabin 25ft off the water! Near shopping, Restaurants, Attractions & Golf!

10.0 out of 10, Exceptional, (27)
"It was a cute little get-away cabin that satisfied our needs. Would stay there again."
Cozy cabin 25ft off the water! Near shopping, Restaurants, Attractions & Golf!
The River Lodge - new look, same place!
Fridge, microwave, oven, stovetop

The River Lodge - new look, same place!

10.0 out of 10, Exceptional, (177)
"Absolutely stunning home on a beautiful piece of property. Quiet, peaceful, and super clean! Can’t recommend enough! "
The River Lodge - new look, same place!
Lakeside Sand Beach House on 3 Acres of fun Near Nisswa and Cross Lake.
Interior

Lakeside Sand Beach House on 3 Acres of fun Near Nisswa and Cross Lake.

9.8 out of 10, Exceptional, (47)
"Great place to stay and an awesome property "
Lakeside Sand Beach House on 3 Acres of fun Near Nisswa and Cross Lake.
Beautiful 5-bedroom house in Enchanting Crosslake -Pontoon Incl with 7 day stay!
TV, fireplace, DVD player, books

Beautiful 5-bedroom house in Enchanting Crosslake -Pontoon Incl with 7 day stay!

2.0 star property
9.8 out of 10, Exceptional, (210)
"It looks good in the pictures, but in person it is fantastic! The Sandy Beach was wonderful, and the facility has more than everything that anyone would ever need. Wonderful family vacation."
Beautiful 5-bedroom house in Enchanting Crosslake -Pontoon Incl with 7 day stay!
River Cabin on the Pine River- Adult only
Property grounds

River Cabin on the Pine River- Adult only

9.8 out of 10, Exceptional, (107)
"Eric and Becky are the absolute best hosts! Highly recommend!"
River Cabin on the Pine River- Adult only
NEW - The Boardwalk on North Long Lake Brainerd with Hot Tub, Pet-Friendly
Pool

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

9.8 out of 10, Exceptional, (24)
"Very clean and plenty of room for big group"
NEW - The Boardwalk on North Long Lake Brainerd with Hot Tub, Pet-Friendly
Eagle Pines: Rare, Beautiful North Shore of Gull Lake
Exterior

Eagle Pines: Rare, Beautiful North Shore of Gull Lake

9.2 out of 10, Wonderful, (48)
"We had a wonderful stay and the cabin was perfect for us!"
Eagle Pines: Rare, Beautiful North Shore of Gull Lake
The Point - On Gull Lake
Fireplace

The Point - On Gull Lake

2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent price"
The price is HK$909
HK$2,190 total
includes taxes & fees
6 Oct - 7 Oct
The Point - On Gull Lake
Popular Interlachen Condo with Relaxing Creek Views & steps away from Gull Lake
Marina

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

9.8 out of 10, Exceptional, (66)
"Great cabin and even better management staff."
Popular Interlachen Condo with Relaxing Creek Views & steps away from Gull Lake
Courtside Cabin-Indoor Sports|Theatre|Hot Tub|
Exterior

Courtside Cabin-Indoor Sports|Theatre|Hot Tub|

9.8 out of 10, Exceptional, (13)
"This place is amazing. The gym was perfect for the grandkids and parents had a blast also ! The kitchen was perfect for food preparation and also enough spaces for everyone to eat. "
Courtside Cabin-Indoor Sports|Theatre|Hot Tub|
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

Sept and Oct dates still open! Clean with lots of Amenities & Gull Chain Access

Sept and Oct dates still open! Clean with lots of Amenities & Gull Chain Access

10/10 Excellent
"Comfy cabin, great location"
marcy b. 2-night trip
Posted 5 days ago
Sept and Oct dates still open! Clean with lots of Amenities & Gull Chain Access

Find out more about Ossipee

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

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?

New Lake Home on Upper Cullen - volleyball, game room, sauna, and lots of trees!: This holiday home rental outside of Ossipee offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Ossipee?

Choose from 7 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.