Cornish-Windsor Covered Bridge

Windsor Vacation 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 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Windsor vacation rentals

Beach

Cabin on the hill Ascutney Vt - 4 bedrooms

Cabin on the hill Ascutney Vt - 4 bedrooms
West Windsor
The price is AED 1,025
AED 1,901 total
includes taxes & fees
23 Jun - 24 Jun
Cabin on the hill Ascutney Vt - 4 bedrooms
House (2 Bedrooms) | Interior

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is AED 940
AED 1,640 total
includes taxes & fees
22 Jun - 23 Jun
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
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 AED 624
AED 1,345 total
includes taxes & fees
22 Jun - 23 Jun
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
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 AED 220
AED 756 total
includes taxes & fees
23 Jun - 24 Jun
Mountain Green
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 AED 881
AED 1,025 total
includes taxes & fees
22 Jun - 23 Jun
Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
Indoor pool

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Okemo Village
10.0 out of 10, Exceptional, (64 reviews)
"Great condo, great location, plenty of room for our family of 5. Flat 800' walk to the slopes. Great hosts."
United States
Nathan C.
The price is AED 1,653
AED 3,084 total
includes taxes & fees
22 Jun - 23 Jun
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
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 AED 496
AED 1,752 total
includes taxes & fees
22 Jun - 23 Jun
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Smart TV, fireplace, books

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great location, "
United States
Bryan R J.
The price is AED 512
AED 1,069 total
includes taxes & fees
23 Jun - 24 Jun
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Family Cabin, 2 Bedrooms, Mountain View | Living room | 40-inch Smart TV with cable channels, TV, Netflix

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 AED 674
AED 1,098 total
includes taxes & fees
22 Jun - 23 Jun
Brook Road Cabin
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 AED 522
AED 1,762 total
includes taxes & fees
22 Jun - 23 Jun
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Hair dryer, towels, soap, shampoo

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is AED 826
AED 2,234 total
includes taxes & fees
22 Jun - 23 Jun
Terrific 3-bedroom cottage with AC in charming Cavendish
House (5 Bedrooms) | Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is AED 4,268
AED 6,783 total
includes taxes & fees
22 Jun - 23 Jun
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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 AED 1,250
AED 3,320 total
includes taxes & fees
22 Jun - 23 Jun
Elysium on Little Sunapee-Dock, Firepit, Trails
Interior

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (40 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is AED 605
AED 1,097 total
includes taxes & fees
22 Jun - 23 Jun
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AED 1,980
AED 3,711 total
includes taxes & fees
27 Jun - 28 Jun
Cozy Vermont Cabin · Mountain Views · Near Okemo
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 AED 1,102
AED 1,999 total
includes taxes & fees
22 Jun - 23 Jun
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Dining

New Ludlow Village Home with Stunning Okemo Mountain View

New Ludlow Village Home with Stunning Okemo Mountain View
Ludlow
10.0 out of 10, Exceptional, (17 reviews)
"Second time we have stayed here. Amazing home, amazing location. The flow and design makes us happy "
United States
karyn r.
The price is AED 985
AED 2,196 total
includes taxes & fees
22 Jun - 23 Jun
New Ludlow Village Home with Stunning Okemo Mountain View
Terrace/patio

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is AED 1,204
AED 3,887 total
includes taxes & fees
22 Jun - 23 Jun
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Dining

Lakeside life at its best!

Lakeside life at its best!
Enfield
9.8 out of 10, Exceptional, (48 reviews)
"The cottage was incredible - perfect layout, accommodations, and attention to detail on all of the features and fixtures. You can tell that the owners are experts at design and building. I would absolutely stay there again."
United States
Keith L.
Lakeside life at its best!
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 AED 1,396
AED 2,551 total
includes taxes & fees
13 Jul - 14 Jul
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
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

Newport Motel

Newport Motel

10/10 Excellent
"The room was huge and super clean. Bathroom needs an update but all in all we would absolutely love to stay again. It was a nice quiet relaxing stay."
Kerri 1-night trip
Posted 1 hour ago
Newport Motel

Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we offer vacation rentals in Windsor close to Maze of Adventure, or you can select a more secluded option if you're looking for extra privacy while you relax. 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's the top vacation rental that Windsor has to offer?

Cozy VT Retreat • Coffee Bar •Fireplace • Near Quechee Gorge • Min to Woodstock: You might want to consider this vacation home rental near Windsor, which 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 you can immerse yourself in your vacation.

How many vacation rentals are there in Windsor?

With 11 Expedia vacation rentals, you're sure 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 vacation rentals like in Windsor?

Vacation rentals are private properties you can stay in for several days or more in Windsor. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.