Ossipee Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

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, (25 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 ￥15,725
￥36,012 total
includes taxes & fees
Apr 27 - Apr 28
Rustic Rose Cottage of Historic West Lebanon
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 ￥19,855
￥25,105 total
includes taxes & fees
Apr 30 - May 1
1 of 2 Enchanting 1 room cabins in Shapleigh, ME located on sloaping forest land
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)
"Excellent stay"
United States
Kara
The price is ￥22,095
￥27,419 total
includes taxes & fees
Apr 16 - Apr 17
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Marina

Cabin for two with lake views & access Now featuring AC Wi-FI and TV

Cabin for two with lake views & access Now featuring AC Wi-FI and TV
Alton
9.4 out of 10, Exceptional, (13 reviews)
"Easy check in, beautiful lake view and plenty dlto do in the area. "
United States
Michele D.
The price is ￥16,256
￥29,863 total
includes taxes & fees
May 11 - May 12
Cabin for two with lake views & access Now featuring AC Wi-FI and TV
Interior

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!

Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Alton
10.0 out of 10, Exceptional, (1 review)
"This is a classic old-style cabin that reminded us of our childhood family trips in the 60’s. It’s not new, but a heck of a lot of fun if you’re in the right head space. Easily walked to town for dinner and to the shore. Clean and had everything we needed."
United States
Christine F.
The price is ￥18,108
￥37,204 total
includes taxes & fees
May 14 - May 15
Cottage in Alton Bay – Sleeps 4, Pool, Trails & More!
Property grounds

Waterfront w/ Prvt Dock & Firepit | Sleeps 8

Waterfront w/ Prvt Dock & Firepit | Sleeps 8
Acton
9.6 out of 10, Exceptional, (15 reviews)
"Love the area & location on the lake!"
United States
Will M.
The price is ￥27,003
￥93,978 total
includes taxes & fees
Apr 16 - Apr 17
Waterfront w/ Prvt Dock & Firepit | Sleeps 8
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 ￥17,472
￥25,970 total
includes taxes & fees
Apr 23 - Apr 24
Ava Jade yurt nestled in the woods of Brownfield, Maine
Interior

Lotus Spa, your home away from home

Lotus Spa, your home away from home
Acton
10.0 out of 10, Exceptional, (50 reviews)
"This place has thought of absolutely everything to make it a cozy and relaxing stay "
United States
Cara L.
The price is ￥28,208
￥49,508 total
includes taxes & fees
Apr 23 - Apr 24
Lotus Spa, your home away from home
Terrace/patio

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath

Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
Wolfeboro
10.0 out of 10, Exceptional, (5 reviews)
"It was very cute and clean, loved the outside area and would def be back again."
United States
Anais & Zach
The price is ￥21,754
￥27,061 total
includes taxes & fees
Apr 16 - Apr 17
Cottage 3 - Year Round - Pet Friendly - 1 Bedroom / 1 Bath
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)
"We really enjoyed our stay. The wood stove was perfect. Would definitely go back."
United States
Alfred C.
The price is ￥19,061
￥27,702 total
includes taxes & fees
Apr 23 - Apr 24
Allie Mae Yurt nestled in the woods
Interior

Rufus III Yurt on the river

Rufus III Yurt on the river
Brownfield
10.0 out of 10, Exceptional, (12 reviews)
"Had a great time,will be back for sure. "
United States
John C.
The price is ￥22,238
￥29,780 total
includes taxes & fees
Apr 22 - Apr 23
Rufus III Yurt on the river
TV

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin

Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Conway
10.0 out of 10, Exceptional, (95 reviews)
"The notes are helpful. Easy check in and out. The house is clean and cozy."
United States
Tessie
The price is ￥19,921
￥37,869 total
includes taxes & fees
Apr 21 - Apr 22
Dog Friendly, Quiet Neighborhood, Cozy lower level cabin
Smart TV

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 ￥9,173
￥33,509 total
includes taxes & fees
Apr 16 - Apr 17
Great Conway Location! Shop Eat Hike Swim
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 ￥20,490
￥46,265 total
includes taxes & fees
May 14 - May 15
Attractive & convenient studio steps to water w/WiFi, water views, & kitchenette
Dining

White Mountains Waterfront Chalet w/ Private Beach

White Mountains Waterfront Chalet w/ Private Beach
Eidelweiss Village
9.8 out of 10, Exceptional, (25 reviews)
"Beautiful home facing the lake. Perfect for a family getaway! "
United States
Navin W.
The price is ￥27,019
￥69,988 total
includes taxes & fees
Apr 19 - Apr 20
White Mountains Waterfront Chalet w/ Private Beach
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 ￥11,156
￥42,506 total
includes taxes & fees
May 1 - May 2
Inviting condo in quiet locale with partial lake views, balcony & grilling area
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 ￥23,826
￥50,726 total
includes taxes & fees
May 14 - May 15
Picturesque studio in bay-front locale just steps to water w/WiFi & 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 ￥21,515
￥60,942 total
includes taxes & fees
May 13 - May 14
Newly Renovated Cottage 4 in Alton Bay, NH
House (1 Bedroom) | Interior

Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is ￥18,646
￥40,483 total
includes taxes & fees
Apr 19 - Apr 20
Hiking & Snowmobile Trails On-site: Alton Retreat!
Terrace/patio

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Alton
9.4 out of 10, Exceptional, (25 reviews)
"Great visit and property as described! Clean, all inclusive, and would recommend. View was beautiful and had a wonderful time."
United States
Catherine M.
The price is ￥23,906
￥58,859 total
includes taxes & fees
Apr 28 - Apr 29
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
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

Days Inn by Wyndham Tamworth

Days Inn by Wyndham Tamworth

6/10 Okay
"Breakfast was good, hit or miss on coffee cups, to find anyone to get some did not go so well, i ended up going to Duncan across the street. If you needed help, it took FOREVER waiting at the front desk to get anyone. When i got into my room it looked like it was not vacuumed in awhile, the fridge stunk, the hotel looks like it was built in the 80’s, with NO improvements made. "
Michelle 3-night trip
Posted 13 hours ago
Days Inn by Wyndham Tamworth

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
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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?

Waterfront cabin near Fish Cove with private dock, water access, firepit, grill: This vacation home rental outside of Ossipee is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

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 Kellerhaus, or get outside and enjoy nature at Lake Winnipesaukee. In the larger area, you’ll find Ossipee Lake Trail and Lake Wentworth.

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.