Ossipee Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Ossipee vacation rentals

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 CA $164
CA $349 total
includes taxes & fees
Jun 2 - Jun 3
Rustic Rose Cottage of Historic West Lebanon

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 CA $157
CA $279 total
includes taxes & fees
Jun 2 - Jun 3
A great cabin with lake views & access! Now Featuring AC/ Wi-Fi- & TV

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 CA $172
CA $218 total
includes taxes & fees
Jun 2 - Jun 3
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land

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 CA $178
CA $338 total
includes taxes & fees
Jun 9 - Jun 10
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

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 CA $150
CA $322 total
includes taxes & fees
Jun 8 - Jun 9
Newly Renovated Cottage on Main Street Alton Bay #5

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)
"The building is in horrible shape but I won't blame the unit owner. The pool was a joke and the attached shopping(?) building was nearly abandoned. The unit could use some updating. The bed was horribly uncomfortable and squeeky. Every movement either my husband or I made was loud and kept us both awake. The velvet bedding was extremely strange in the heat of summer and was uncomfortable. The shower/tub bottom did not feel secure and felt like the plastic was going to fall through the floor. To...
United States
Lisa R.
The price is CA $105
CA $381 total
includes taxes & fees
Jun 2 - Jun 3
Inviting condo in quiet locale with partial lake views, balcony & grilling area

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 CA $186
CA $413 total
includes taxes & fees
Jun 2 - Jun 3
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette

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 CA $192
CA $538 total
includes taxes & fees
Jun 8 - Jun 9
Newly Renovated Cottage 4 in Alton Bay, NH

Stay on Historic Estate! Quiet Limerick Escape

Stay on Historic Estate! Quiet Limerick Escape
3.0 star property
Limerick
The price is CA $219
CA $409 total
includes taxes & fees
Jun 2 - Jun 3
Stay on Historic Estate! Quiet Limerick Escape

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 CA $152
CA $226 total
includes taxes & fees
Jun 7 - Jun 8
Ava Jade yurt nestled in the woods of Brownfield, Maine

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 CA $217
CA $453 total
includes taxes & fees
Jun 2 - Jun 3
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

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 traveller
The price is CA $212
CA $261 total
includes taxes & fees
Jun 2 - Jun 3
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard

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 CA $109
CA $324 total
includes taxes & fees
Jun 3 - Jun 4
Great Conway Location! Shop Eat Hike Swim

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 CA $166
CA $241 total
includes taxes & fees
Jun 2 - Jun 3
Allie Mae Yurt nestled in the woods

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 CA $194
CA $210 total
includes taxes & fees
Jun 2 - Jun 3
Danforth Bay Camping and RV Resort

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 CA $222
CA $274 total
includes taxes & fees
Jun 3 - Jun 4
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

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 CA $186
CA $413 total
includes taxes & fees
Jun 2 - Jun 3
Cozy hotel-style suite right on the water, shared patio, free WiFi

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 CA $190
CA $372 total
includes taxes & fees
Jun 8 - Jun 9
Lake View Cedar Lodge Room w/ Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is CA $266
CA $467 total
includes taxes & fees
Jun 2 - Jun 3
Cedar Lodge Room 2 Queen Beds & Private Balcony

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 CA $193
CA $256 total
includes taxes & fees
Jun 2 - Jun 3
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ossipee Hotel Reviews

Find out more about Ossipee

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ossipee. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.