Windsor Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Windsor

Lakefront Cabin in Beautiful, Quiet Location

Lakefront Cabin in Beautiful, Quiet Location

Spectacular Log Home with Private Lake Access

10.0 out of 10, Exceptional, (95)
"Wonderful 3 night stay in this beautiful log home. Access to the lake, dock and kayaks was a bonus. We had a blast on the lake and did a good amount of fishing. We will definitely be back! "
Spectacular Log Home with Private Lake Access

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

9.8 out of 10, Exceptional, (18)
"Property was clean and super close to the downtown square! "
The price is NZ$281
includes taxes & fees
15 July - 16 July
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Cozy & bright getaway close to ski mountains and lake

10.0 out of 10, Exceptional, (27)
"Immaculate, well decorated, and well supplied. Steps from the clearest water, family-friendly lake. We wanted for nothing. I would recommend this to everyone I know. "
Cozy & bright getaway close to ski mountains and lake

Dog Friendly Lakefront Lodge

10.0 out of 10, Exceptional, (3)
"Great house, awesome pond"
Dog Friendly Lakefront Lodge

Charming Lake Sunapee & Mt. Sunapee Ski Cabin

9.6 out of 10, Exceptional, (23)
"Great get away on lake Sunapee, great house just a short walk to the lake. Great place to relax and take in the sun set on the dock or grilling on the deck. Well equipped home that is super clean,just a great getaway. "
Charming Lake Sunapee & Mt. Sunapee Ski Cabin

Beautiful Private Lakefront new Log Home

9.8 out of 10, Exceptional, (54)
"This was our second time renting this house. We love the location and everything about it. We have a large family and the house is more than big enough for everyone and the lake is beautiful."
The price is NZ$2,112
includes taxes & fees
12 July - 13 July
Beautiful Private Lakefront new Log Home

Downtown Hot Tub Escape

9.2 out of 10, Wonderful, (15)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
Downtown Hot Tub Escape

"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

10.0 out of 10, Exceptional, (2)
"We had the most amazing stay at Leah and Chris’s beautiful home! From the moment we arrived, we were blown away by how clean, spacious, and thoughtfully stocked the house was—it truly had everything we could possibly need and more.Our group of 12 (including young kids and dogs!) had tons of space to spread out comfortably, and every single bed was super cozy. The huge yard was perfect for lawn games, which were conveniently provided, and we spent hours outside enjoying the privacy and peaceful...
The price is NZ$1,966
includes taxes & fees
13 July - 14 July
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life

Lake Sunapee Cozy Cottage - Blodgett Landing

9.6 out of 10, Exceptional, (46)
"We truly enjoyed the chance to escape from a busy city week and relax at Lake Sunapee on their dock, play games in the cottage, and going for a moderate hike on Mt. Kearsarge!"
Lake Sunapee Cozy Cottage - Blodgett Landing

Private NH Escape | Cozy Fireplace & Deck

6.0 out of 10, (2)
"The property did not indicate this was a top floor condo. I have mobility issues and this was a real problem. There were several hairs on the bed sheets. I contacted the manager and he never responded. Washed everything myself including the mattress pad which had flakey debris on it, because we couldn’t just leave and lose our . Plus all our heavy luggage was painstakingly brought upstairs at this point. After a 5 night stay we still never heard from the Manager. This is not acceptable. ...
The price is NZ$392
includes taxes & fees
13 July - 14 July
Private NH Escape | Cozy Fireplace & Deck

Charming Lake House in Beautiful Newbury, NH

Charming Lake House in Beautiful Newbury, NH

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

10.0 out of 10, Exceptional, (15)
"We loved our stay here. House was very tidy, property owner easy to communicate with, and location great right by the lake and mountain. There are also a few nice hikes nearby. "
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

Unique Cozy private 1-bedroom apartment in charming Temple

10.0 out of 10, Exceptional, (1)
"The location was a bit hard to find with any online map, it’s not accurate. But with a bit of driving, easily found! It was lovely, peaceful, and cool during a hot weekend so nice and relaxing!"
The price is NZ$716
includes taxes & fees
20 July - 21 July
Unique Cozy private 1-bedroom apartment in charming Temple

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

10.0 out of 10, Exceptional, (10)
"This place is so cute! It has everything you need, very clean, beds are comfy and it’s so cozy. The owner is very quick to respond with any questions. We highly recommend it here!"
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!

10.0 out of 10, Exceptional, (158)
"We love the house, it had everything we needed!"
Amazing Mt. Sunapee Region Home Convenient for many activities! Winter Is Open!

Charming cabin in delightful Greenfield New Hampshire with WiFi access

10.0 out of 10, Exceptional, (1)
The price is NZ$437
includes taxes & fees
17 July - 18 July
Charming cabin in delightful Greenfield New Hampshire with WiFi access

20% Sale April/May NH Condo Unit 2D

The price is NZ$362
includes taxes & fees
10 July - 11 July
20% Sale April/May NH Condo Unit 2D

Berry Mountain Lodge: Spacious 5-bedroom house close to skiing and Lake Sunapee

Berry Mountain Lodge: Spacious 5-bedroom house close to skiing and Lake Sunapee

Cabin: Private Hot Tub, Walk to Pats Peak Ski Area

9.8 out of 10, Exceptional, (27)
"Love this property! This was our 2nd time staying. A great log cabin feel within walking distance to the mountain!"
Cabin: Private Hot Tub, Walk to Pats Peak Ski Area
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

Frequently asked questions

Can I find a holiday rental in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, 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 Windsor has to offer?

Charming Lake Sunapee & Mt. Sunapee Ski Cabin: This holiday home rental outside Windsor is located near skiing, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals will I find in Windsor?

Expedia has 5 holiday rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as Eaton's Magic Morsel, or get out into nature at a spot like Black Pond. In the wider area, you’ll find Windsor Town Hall and Franklin Pierce Homestead.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.