Ossipee Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Ossipee holiday rentals

Interior

Lotus Spa, your home away from home

Lotus Spa, your home away from home
Acton
10.0 out of 10, Exceptional, (48 reviews)
"the property is gorgeous and exactly what we needed for a little getaway! "
United States
Allie K.
The price is HK$1,231
HK$2,262 total
includes taxes & fees
22 Feb - 23 Feb
Lotus Spa, your home away from home
Sauna

Rustic Rose Cottage of Historic West Lebanon

Rustic Rose Cottage of Historic West Lebanon
Lebanon
10.0 out of 10, Exceptional, (24 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 HK$1,008
HK$1,968 total
includes taxes & fees
21 Feb - 22 Feb
Rustic Rose Cottage of Historic West Lebanon
Outdoor dining

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Wolfeboro
10.0 out of 10, Exceptional, (17 reviews)
"Booked a summer getaway for my husband, my dog, and me. We had a great time - the house was comfortable and clean, and the location was excellent! "
United States
Laura B.
The price is HK$1,875
HK$4,239 total
includes taxes & fees
22 Feb - 23 Feb
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Fridge, microwave, oven, stovetop

Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway
Gilford
10.0 out of 10, Exceptional, (73 reviews)
"Amazing spot!"
United States
David E.
The price is HK$3,165
HK$4,892 total
includes taxes & fees
5 Mar - 6 Mar
Idyllic Mountain and Lake Getaway
Smart TV, fireplace

Cozy three bedroom house located just five minutes from Lake Winnipesaukee

Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Wolfeboro
8.0 out of 10, Very good, (17 reviews)
"Thanks for a great stay!"
United States
Lynne Q.
The price is HK$1,582
HK$2,709 total
includes taxes & fees
20 Feb - 21 Feb
Cozy three bedroom house located just five minutes from Lake Winnipesaukee
Outdoor dining

[NEW] Cozy Cabin near Gunstock & Lake Winni

[NEW] Cozy Cabin near Gunstock & Lake Winni
Gilford
The price is HK$1,891
HK$4,732 total
includes taxes & fees
25 Feb - 26 Feb
[NEW] Cozy Cabin near Gunstock & Lake Winni
Smart TV

Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access

Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access
Newfield
10.0 out of 10, Exceptional, (3 reviews)
"I stayed here for the 4th of July weekend and had a wonderful time! You can really tell the host put a lot of thought and detail to every little thing on the inside and outside. There was a lot of nice features throughout like the hidden sauna, hot tub, fire pit, swinging chairs, etc. "
United States
Stephanie S.
The price is HK$1,871
HK$3,155 total
includes taxes & fees
23 Feb - 24 Feb
Welcome to THE NEST, HotTub/Sauna/Rock Haven Lake access
Exterior

Meredith Bay - Brand New 1st Floor Apartment In Private Home

Meredith Bay - Brand New 1st Floor Apartment In Private Home
Meredith
9.8 out of 10, Exceptional, (45 reviews)
"Very clean and very comfortable. Short walk to downtown made our stay perfect. "
United States
Julian G.
The price is HK$1,160
HK$2,378 total
includes taxes & fees
23 Feb - 24 Feb
Meredith Bay - Brand New 1st Floor Apartment In Private Home
Beach nearby

Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit

Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
Wolfeboro
9.4 out of 10, Exceptional, (3 reviews)
"The two connected Cottages were Perfect for myself husband & teenage daughter. Loved the private outdoor space & firepit! Onsite manager was super accessible and really helpful! Will definitely be back!!"
United States
Dorenda W.
The price is HK$2,722
HK$3,344 total
includes taxes & fees
21 Feb - 22 Feb
Cottage 5-6 - Year Round Pet Friendly - 2 Bedroom / 1 Bath End Unit
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 property. Loved our stay and the owners were great! Definitely will book again "
United States
Marcus
The price is HK$1,168
HK$1,446 total
includes taxes & fees
22 Feb - 23 Feb
Cottage 4 - Year Round Pet Friendly 1 Bed w/ Loft / 1 Bath & Courtyard
Property grounds

Private lakeside home with 2 private docks, hot tub, bball hoop, H2o activities

Private lakeside home with 2 private docks, hot tub, bball hoop, H2o activities
Shapleigh
9.8 out of 10, Exceptional, (35 reviews)
"Excellent location! Quiet and beautiful! Very comfortable home!"
United States
Heather L.
The price is HK$4,747
HK$9,305 total
includes taxes & fees
24 Feb - 25 Feb
Private lakeside home with 2 private docks, hot tub, bball hoop, H2o activities
Fridge, microwave, oven, stovetop

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home

Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
Meredith
10.0 out of 10, Exceptional, (171 reviews)
"We loved our stay, the apartment was in the heart of town, very clean and comfortable! The hosts were very responsive and accommodating. "
United States
Erin S.
The price is HK$1,211
HK$2,468 total
includes taxes & fees
22 Feb - 23 Feb
Meredith Bay - Brand New 2nd and 3rd floor Apartment in Private Home
Interior

Welcome to the Z E N

Welcome to the Z E N
Acton
9.6 out of 10, Exceptional, (14 reviews)
"Nice little escape without being too far from everything. Gesine was a great host as usual"
United States
Kate-Lynn P.
The price is HK$1,469
HK$2,487 total
includes taxes & fees
5 Mar - 6 Mar
Welcome to the Z E N
Interior

Lake Winni Waterfront Condo

Lake Winni Waterfront Condo
Gilford
The price is HK$1,489
HK$2,965 total
includes taxes & fees
22 Feb - 23 Feb
Lake Winni Waterfront Condo
Exterior

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile

Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
Brownfield
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great for check in, and the amenities and snacks there were a great touch! Came in handy for the couple that forgot to pack their toothbrushes! "
United States
Brian A.
The price is HK$1,100
HK$2,315 total
includes taxes & fees
3 Mar - 4 Mar
Lakehouse Near N. Conway &Skiing/Pool table/Pond Access to Fish/Skate/Snowmobile
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)
"House was cozy, well appointed, spotlessly clean and just as advertised on the site. We had a wonderful visit and would love to visit again."
United States
Tracy K.
The price is HK$1,582
HK$3,675 total
includes taxes & fees
2 Mar - 3 Mar
White Mountains Waterfront Chalet w/ Private Beach
Beach nearby

Cozy Cabin near Tuftonboro & Lake Winnipesaukee

Cozy Cabin near Tuftonboro & Lake Winnipesaukee
Tuftonboro
9.6 out of 10, Exceptional, (5 reviews)
"Beautiful property "
United States
Keith B.
The price is HK$1,297
HK$3,511 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Cabin near Tuftonboro & Lake Winnipesaukee
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 location, easy access and very clean. The only negative was the paper-thin walls or should I say neighbors that did not think of anyone else or their neighbors."
United States
Lisa D.
The price is HK$1,172
HK$2,818 total
includes taxes & fees
5 Mar - 6 Mar
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
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 HK$938
HK$1,363 total
includes taxes & fees
23 Feb - 24 Feb
Allie Mae Yurt nestled in the woods
Smart TV, fireplace, video games, table football

Mountain View Home with Hot Tub – Sleeps 10

Mountain View Home with Hot Tub – Sleeps 10
Conway
9.6 out of 10, Exceptional, (27 reviews)
"Clean house and well stocked, pet friendly, close to town and attractions, owner communicated very well. Great stay!"
United States
Linda S.
The price is HK$2,290
HK$5,503 total
includes taxes & fees
12 Mar - 13 Mar
Mountain View Home with Hot Tub – Sleeps 10
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossipee Hotel Reviews

Merrill Farm Inn

Merrill Farm Inn

10/10 Excellent
"This place is my favorite. Absolute best overall, excellent room variety for all family sizes, excellent breakfast and great customer service."
Jaclyn 2-night trip
Posted 3 days ago
Merrill Farm Inn

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!

Frequently asked questions

Can I find a holiday rental 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.

What are some of the best holiday rentals that Ossipee has to offer?

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski: This holiday home rental outside of Ossipee is located on a lake, and has an indoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Ossipee?

With 7 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Wentworth State Park and Ossipee Lake Trail.

What’s a holiday rental in Ossipee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossipee. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.