Cornish-Windsor Covered Bridge

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Windsor holiday rentals

Beach

Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is HK$2,186
HK$4,053 total
includes taxes & fees
26 Jun - 27 Jun
Cabin on the hill Ascutney Vt - 4 bedrooms
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"We had a very lovely stay. The kitchen was well-equipped and the whole home was very cozy. There was wood for the wood stove and lots of games and puzzles to do. Check-in and check-out was simple. Just what we were looking for! "
United States
Eleanor D.
The price is HK$1,332
HK$2,869 total
includes taxes & fees
22 Jun - 23 Jun
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Property grounds

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
South Royalton
The price is HK$1,861
HK$2,160 total
includes taxes & fees
25 Jun - 26 Jun
Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
Exterior

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck

Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Newbury
10.0 out of 10, Exceptional, (30 reviews)
"The Treehouse provided an excellent retreat. Beautiful property and excellent hosts. "
United States
T G.
The price is HK$2,468
HK$4,251 total
includes taxes & fees
22 Jun - 23 Jun
Luxury Treehouse Near Mount Sunapee | Fireplace + Deck
Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (12 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,191
HK$2,475 total
includes taxes & fees
22 Jun - 23 Jun
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Outdoor dining

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
South Royalton
The price is HK$1,015
HK$1,191 total
includes taxes & fees
24 Jun - 25 Jun
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
Smart TV, fireplace

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is HK$1,114
HK$3,758 total
includes taxes & fees
22 Jun - 23 Jun
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Interior

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away

Perfect Lake or Mountain Getaway Less Than 5 Minutes Away
Sunapee
10.0 out of 10, Exceptional, (26 reviews)
"Great location. Great house for a family ski vacation. "
United States
Marianne H.
Perfect Lake or Mountain Getaway Less Than 5 Minutes Away
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is HK$1,199
HK$3,922 total
includes taxes & fees
24 Jun - 25 Jun
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
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$1,439
HK$2,343 total
includes taxes & fees
21 Jun - 22 Jun
Brook Road Cabin
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, (21 reviews)
"Beautiful house and convenient location for a family ski trip. We'lll be back in the summer! "
United States
Rebecca B.
The price is HK$2,978
HK$5,441 total
includes taxes & fees
13 Jul - 14 Jul
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
TV, fireplace, computer monitors

Elysium on Little Sunapee-Dock, Firepit, Trails

Elysium on Little Sunapee-Dock, Firepit, Trails
New London
9.8 out of 10, Exceptional, (14 reviews)
"Great Lake house with all the amenities you need for a great week!! Kitchen is well stocked. Wonderful hosts!"
United States
Caren H.
The price is HK$2,643
HK$7,049 total
includes taxes & fees
22 Jun - 23 Jun
Elysium on Little Sunapee-Dock, Firepit, Trails
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (25 reviews)
"I enjoy the location "
United States
troy
The price is HK$468
HK$1,612 total
includes taxes & fees
23 Jun - 24 Jun
Mountain Green
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (111 reviews)
"Clean great cozy place!"
United States
Himanshu P.
The price is HK$2,029
HK$3,868 total
includes taxes & fees
13 Jul - 14 Jul
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Interior

Perfect 2-bedroom in charming Newport

Perfect 2-bedroom in charming Newport
Newport
Perfect 2-bedroom in charming Newport
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (19 reviews)
"We really enjoyed our stay! It was close to Okemo and it was so nice to relax in the hot tub after a day of skiing. We would definitely stay here again! "
United States
Dana C.
The price is HK$1,291
HK$2,340 total
includes taxes & fees
21 Jun - 22 Jun
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Smart TV, video games, books

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee

Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Sunapee
9.6 out of 10, Exceptional, (8 reviews)
"Great stay, the boys will be back! "
United States
Susan B.
The price is HK$3,525
HK$6,315 total
includes taxes & fees
29 Jun - 30 Jun
Charming 3-Bedroom House. Walk to Sunapee Harbor and Short Drive to Mt. Sunapee
Outdoor pool, a heated pool

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (23 reviews)
"Great location, and comfortable for the whole family. Everyone in the enjoyed the open living room and dining room, plus the privacy of their own bedroom space. "
United States
Ania H.
The price is HK$2,350
HK$4,229 total
includes taxes & fees
1 Jul - 2 Jul
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is HK$3,395
HK$12,231 total
includes taxes & fees
21 Jun - 22 Jun
Breakaway House by Killington Vacation Rentals
Bathroom

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The Suites at Killington Center
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

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent
"Our room is very clean. The hot tub was really nice. And all the staff was very friendly and helpful."
jennifer 1-night trip
Posted 1 hour ago
Killington Mountain Lodge, Tapestry Collection by Hilton

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 in Windsor close to Maze of Adventure, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its breweries and golf courses. Make sure you have time to check out the forests while you're in the area.

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

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock: This holiday home rental outside of Windsor is located on a river, and has an outdoor pool, a fireplace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windsor?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What can I see and do in Windsor?

Connecticut River and Paradise Park are a couple of scenic spots to enjoy the outdoors, whereas American Precision Museum is one of the cultural attractions. Other places in town to visit include Harpoon Brewery and Brownsville Trail.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature amenities such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy 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 traditional hotel, which is another reason why a holiday rental is a popular option for a family trip or a small group gathering.