Ossipee Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Ossipee vacation rentals

Sauna

Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (26 reviews)
"Everything about our stay was lovely! Check-in was smooth, the property was gorgeous, and the cottage was full of charm. "
United States
Daniel S.
The price is ￥17,998
￥38,714 total
includes taxes & fees
Jun 1 - Jun 2
Rustic Rose Cottage of Historic West Lebanon
Beach

A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV

A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV
Alton
9.4 out of 10, Exceptional, (13 reviews)
"great location loved the cabin it was just enough"
United States
michelle w.
The price is ￥18,157
￥31,927 total
includes taxes & fees
Jun 1 - Jun 2
A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV
Property grounds

1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
Shapleigh
9.0 out of 10, Wonderful, (4 reviews)
"Stayed for 2 nights and had a wonderful relaxing time. Very kind and repsonsive hosts. We especially loved the fire pit. Would stay again in a heart beat. "
United States
Bethany K.
The price is ￥19,909
￥25,173 total
includes taxes & fees
Jun 2 - Jun 3
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
TV

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Conway
10.0 out of 10, Exceptional, (97 reviews)
"Great place to stay. Very clean. Incredibly thorough. Very welcoming to pets. "
United States
Nathan
The price is ￥20,705
￥39,574 total
includes taxes & fees
Jun 8 - Jun 9
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Exterior

Newly Renovated Cottage on Main Street Alton Bay #5

Newly Renovated Cottage on Main Street Alton Bay #5
Alton
10.0 out of 10, Exceptional, (1 review)
"Great places. Quiet and quaint and close to the lake and restaurants. Will rent again "
United States
Brian B.
The price is ￥17,360
￥36,958 total
includes taxes & fees
Jun 1 - Jun 2
Newly Renovated Cottage on Main Street Alton Bay #5
Pool

Inviting condo in quiet locale with partial lake views, balcony & grilling area

Inviting condo in quiet locale with partial lake views, balcony & grilling area
Gilford
8.4 out of 10, Very Good, (17 reviews)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is ￥12,105
￥43,784 total
includes taxes & fees
Jun 1 - Jun 2
Inviting condo in quiet locale with partial lake views, balcony & grilling area
Outdoor dining

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Alton
9.0 out of 10, Wonderful, (22 reviews)
"Great little gem given its price, location, and overall accommodations! "
United States
Kevin R.
The price is ￥21,501
￥47,175 total
includes taxes & fees
Jun 1 - Jun 2
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
TV

Newly Renovated Cottage 4 in Alton Bay, NH

Newly Renovated Cottage 4 in Alton Bay, NH
Alton
9.0 out of 10, Wonderful, (4 reviews)
"Communication was amazing, check in was a delightful, the house itself was perfect "
United States
Jennifer S.
The price is ￥23,413
￥62,987 total
includes taxes & fees
Jun 10 - Jun 11
Newly Renovated Cottage 4 in Alton Bay, NH
Apartment (0 Bedroom) | Front of property

Stay on Historic Estate! Quiet Limerick Escape

Stay on Historic Estate! Quiet Limerick Escape
3.0 star property
Limerick
The price is ￥25,324
￥47,249 total
includes taxes & fees
Jun 1 - Jun 2
Stay on Historic Estate! Quiet Limerick Escape
Interior

Ava Jade yurt nestled in the woods of Brownfield, Maine

Ava Jade yurt nestled in the woods of Brownfield, Maine
Brownfield
10.0 out of 10, Exceptional, (19 reviews)
"Beautiful , clean , secluded Yurt . We truly enjoyed our stay "
United States
Judy S.
The price is ￥17,520
￥26,041 total
includes taxes & fees
Jun 1 - Jun 2
Ava Jade yurt nestled in the woods of Brownfield, Maine
Property grounds

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Alton
8.6 out of 10, Excellent, (18 reviews)
"Nice location on the lake."
United States
Mary L.
The price is ￥25,005
￥52,011 total
includes taxes & fees
Jun 1 - Jun 2
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Terrace/patio

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Wolfeboro
9.6 out of 10, Exceptional, (11 reviews)
"Great place "
United States
Anonymous traveler
The price is ￥24,018
￥29,862 total
includes taxes & fees
Jun 3 - Jun 4
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Smart TV, fireplace

Great Conway Location! Shop Eat Hike Swim

Great Conway Location! Shop Eat Hike Swim
Settlers Green
7.8 out of 10, Good, (26 reviews)
"Room was clean enough, but the location in the midst of a outlet mall left a lot to be desired for a stop on a leaf peeping vacation."
United States
Kelly C.
The price is ￥12,543
￥37,464 total
includes taxes & fees
Jun 1 - Jun 2
Great Conway Location! Shop Eat Hike Swim
Outdoor dining

Allie Mae Yurt nestled in the woods

Allie Mae Yurt nestled in the woods
Brownfield
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful property! Comfortable and clean lodging. "
United States
Ian M.
The price is ￥19,112
￥27,776 total
includes taxes & fees
Jun 1 - Jun 2
Allie Mae Yurt nestled in the woods
Exterior

Danforth Bay Camping and RV Resort

Danforth Bay Camping and RV Resort
2.0 star property
Freedom
8.4 out of 10, Very Good, (15 reviews)
"Family- friendly Beautiful all around Soo many things to do you can never get bored Enjoyed every minute of it "
United States
Roxanna
The price is ￥22,344
￥24,242 total
includes taxes & fees
Jun 1 - Jun 2
Danforth Bay Camping and RV Resort
Beach nearby

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Wolfeboro
10.0 out of 10, Exceptional, (18 reviews)
"This is a great place to stay with a dog"
United States
David M.
The price is ￥25,467
￥31,607 total
includes taxes & fees
Jun 3 - Jun 4
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Property grounds

Cozy hotel-style suite right on the water, shared patio, free WiFi

Cozy hotel-style suite right on the water, shared patio, free WiFi
Alton
8.8 out of 10, Excellent, (17 reviews)
"One of our favorite places to stay in this area."
United States
Anthony G.
The price is ￥21,501
￥47,175 total
includes taxes & fees
Jun 1 - Jun 2
Cozy hotel-style suite right on the water, shared patio, free WiFi
Exterior

Lake View Cedar Lodge Room w/ Private Balcony

Lake View Cedar Lodge Room w/ Private Balcony
Weirs Beach
9.4 out of 10, Exceptional, (19 reviews)
"Great place"
United Kingdom
Amy C.
The price is ￥21,900
￥42,422 total
includes taxes & fees
Jun 8 - Jun 9
Lake View Cedar Lodge Room w/ Private Balcony
Exterior

Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is ￥30,659
￥53,869 total
includes taxes & fees
Jun 1 - Jun 2
Cedar Lodge Room 2 Queen Beds & Private Balcony
Interior

Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (13 reviews)
"Had a great time,will be back for sure. "
United States
John C.
The price is ￥22,298
￥29,687 total
includes taxes & fees
Jun 1 - Jun 2
Rufus III Yurt on the river
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

Gunstock Inn & Suites

Gunstock Inn & Suites

10/10 Excellent
"Welcoming staff and lovely service dog. Clean room. Comfortable bed."
Michael 1-night trip
Posted 1 hour ago
Gunstock Inn & Suites

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:

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

Frequently asked questions

Can I find a vacation rental in Ossipee?

Yes, we offer vacation rentals close to the most popular points of interest in Ossipee, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Ossipee?

Couples Villa Retreat w/85” Sony HD 8K TV Pool table New Jacuzzi Spa & Game room: This vacation home rental outside of Ossipee is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Ossipee?

With 7 Expedia vacation rentals, you're sure to find just the right place for your Ossipee stay.

What’s there to see and do in Ossipee?

While exploring the area, visit family-friendly sights like Stand Up Paddleboard NH, or get outside and enjoy nature at Lake Winnipesaukee. In the larger area, you’ll find Belleau Lake and Ossipee Lake Trail.

What’s a vacation rental in Ossipee like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Ossipee. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for family gatherings.