Windsor Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Windsor holiday rentals

Exterior detail

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

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (33 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is HK$529
HK$1,169 total
includes taxes & fees
1 Apr - 2 Apr
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Beach

"Seacoast" at Keyser Pond Campground

"Seacoast" at Keyser Pond Campground
Henniker
10.0 out of 10, Exceptional, (2 reviews)
"Very comfortable space - clean and cozy!"
United States
Ingrid K.
The price is HK$1,214
HK$1,770 total
includes taxes & fees
1 Apr - 2 Apr
"Seacoast" at Keyser Pond Campground
Fridge, microwave, oven, stovetop

Chic Farmhouse Decor | Deck w/View

Chic Farmhouse Decor | Deck w/View
Sunapee
10.0 out of 10, Exceptional, (57 reviews)
"Loved our stay and will definitely return!"
United States
Jenifer S.
The price is HK$1,480
HK$3,238 total
includes taxes & fees
31 Mar - 1 Apr
Chic Farmhouse Decor | Deck w/View
Exterior detail

Brook Road Condo

Brook Road Condo
Goshen
8.8 out of 10, Excellent, (15 reviews)
"Location was great"
United States
Andrew P.
The price is HK$1,331
HK$2,524 total
includes taxes & fees
1 Apr - 2 Apr
Brook Road Condo
Interior

Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking

Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Bennington
10.0 out of 10, Exceptional, (12 reviews)
"Good 2-bedroom cabin close to Crotched skiing/boarding. Scenic frozen lake views. Cozy beds. Nice!"
United States
Matthew
The price is HK$1,434
HK$2,925 total
includes taxes & fees
13 Apr - 14 Apr
Peaceful Family Friendly Private Lake Waterfront Home Close to Beach and Hiking
Beach towels

Relaxing Hot Tub Getaway

Relaxing Hot Tub Getaway
Antrim
9.4 out of 10, Exceptional, (16 reviews)
"We wanted a place where we could eat and spend time together while still having space for everyone else to stretch out and this hit all the right buttons. Family weekend to visit our grandson, a student at nearby NEC, After a 3 hour drive up from the Cape, followed by an afternoon at the mall and restocking his dorm room, the hot tub was just what the doctor ordered!Rebecca is a wonderful host, very responsive, friendly, and helpful!"
United States
Jean C.
The price is HK$1,050
HK$1,972 total
includes taxes & fees
7 Apr - 8 Apr
Relaxing Hot Tub Getaway
Terrace/patio

Private Hot Tub Suite

Private Hot Tub Suite
Antrim
8.4 out of 10, Very good, (11 reviews)
"Host was communicative and helpful with some specific questions we had. The apartment was in a cute older house, nicely updated and set up for guests. Everything was nicely labeled to be easy to find. The hot tub was great as well!"
United States
Sarah H.
The price is HK$1,050
HK$2,006 total
includes taxes & fees
2 Apr - 3 Apr
Private Hot Tub Suite
Property grounds

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

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Newbury
10.0 out of 10, Exceptional, (19 reviews)
"We loved our weekend experience at the Hideaway! "
United States
Benjamin M.
The price is HK$1,480
HK$3,535 total
includes taxes & fees
2 Apr - 3 Apr
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Interior

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi

Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Greenfield
10.0 out of 10, Exceptional, (15 reviews)
"Charming location and beautiful setting. "
United States
Cherie G.
The price is HK$1,175
HK$1,700 total
includes taxes & fees
3 Apr - 4 Apr
Charming 16x16 pine cabin in delightful Greenfield New Hampshire with WiFi
Exterior

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

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
Newport
9.8 out of 10, Exceptional, (21 reviews)
"The treehouse was the perfect place to unwind and relax for a few nights. Seeing the pines covered in snow out of every window was truly magical. Clean, well stocked, and everything was in good working order. "
United States
Ashley P.
The price is HK$1,410
HK$2,940 total
includes taxes & fees
1 Apr - 2 Apr
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River
TV

Brook Road Cabin

Brook Road Cabin
Goshen
9.8 out of 10, Exceptional, (17 reviews)
"Would go back!"
United States
Elizabeth C.
The price is HK$1,394
HK$2,592 total
includes taxes & fees
31 Mar - 1 Apr
Brook Road Cabin
Exterior

Unique Treehouse Near Mt Sunapee

Unique Treehouse Near Mt Sunapee
Newbury
10.0 out of 10, Exceptional, (29 reviews)
"Amazing property! Would definitely stay here again "
New Zealand
Jackie M.
The price is HK$1,798
HK$3,404 total
includes taxes & fees
2 Apr - 3 Apr
Unique Treehouse Near Mt Sunapee
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (20 reviews)
"Amazing place, cozy, clean and organized. I loved it and I want to come back again."
United States
Alex F.
The price is HK$2,154
HK$2,558 total
includes taxes & fees
13 Apr - 14 Apr
Owl's Nest Treehouse
Interior

Spring Ski vacation bookings are here and NH Maple Weekend!

Spring Ski vacation bookings are here and NH Maple Weekend!
Sutton
10.0 out of 10, Exceptional, (19 reviews)
"Perfect house for our stay!"
United States
Shelley R.
The price is HK$1,410
HK$3,195 total
includes taxes & fees
31 Mar - 1 Apr
Spring Ski vacation bookings are here and NH Maple Weekend!
Beach

"White Mountains" cabin at Keyser Pond Campground

"White Mountains" cabin at Keyser Pond Campground
Merrimack County
The price is HK$1,214
HK$1,778 total
includes taxes & fees
1 Apr - 2 Apr
"White Mountains" cabin at Keyser Pond Campground
TV, fireplace, books

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Sunapee
10.0 out of 10, Exceptional, (20 reviews)
"Great home. The hosts were accessible and responded quickly to questions. Definitely will stay there again!"
United States
Ellen V.
The price is HK$1,198
HK$3,399 total
includes taxes & fees
5 Apr - 6 Apr
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
Exterior

Waterfront Family Getaway with Sunroom & Stunning Views

Waterfront Family Getaway with Sunroom & Stunning Views
Washington
The price is HK$1,064
HK$2,719 total
includes taxes & fees
8 Apr - 9 Apr
Waterfront Family Getaway with Sunroom & Stunning Views
Property grounds

Lake Front Family Friendly Escape

Lake Front Family Friendly Escape
Newport
10.0 out of 10, Exceptional, (4 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
United States
Ann R.
The price is HK$846
HK$2,702 total
includes taxes & fees
31 Mar - 1 Apr
Lake Front Family Friendly Escape
Living room

Brook Road Cabin

Brook Road Cabin
3.5 star property
Goshen
7.8 out of 10, Good, (9 reviews)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
The price is HK$1,438
HK$2,342 total
includes taxes & fees
31 Mar - 1 Apr
Brook Road Cabin
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 Windsor Hotel Reviews

Riverhouse by Weekender (Formerly Jack Daniels Inn)

Riverhouse by Weekender (Formerly Jack Daniels Inn)

6/10 Okay
"Though clean and spacious, the room faced the busy road, not the river, so be aware that the photos are misleading."
Julie 2-night trip
Posted 2 hours ago
Riverhouse by Weekender (Formerly Jack Daniels Inn)

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

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

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?

Beautiful Private Lakefront new Log Home: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.