Vacation Rentals in Windsor County

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Top Cities in Windsor County

Top Vacation Rentals in Windsor County

Pet-friendly winter retreat in the woods near Okemo + Killington

2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Excellent week at a cozy property, convenient to Killington and Okemo. Easy check in and check out; highly responsive and helpful host. Would recommend to those looking for a great VT escape."
United States
Amanda L.
$403 nightly
The price is $451
Nov 16 - Nov 17
Total with taxes and fees
Pet-friendly winter retreat in the woods near Okemo + Killington

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

2.0 star property
Cavendish
10.0 out of 10, Exceptional, (9)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
United States
Nicholas M.
$283 nightly
The price is $308
Nov 20 - Nov 21
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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

Sharon
10.0 out of 10, Exceptional, (2)
"Cabin was spotless and exactly what I expected"
United States
mark g.
$235 nightly
The price is $264
Dec 2 - Dec 3
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"The location as well as the attention to details was absolutely amazing!"
United States
Amy F.
$171 nightly
The price is $187
Nov 15 - Nov 16
Total with taxes and fees
Treehouse at Wise Pines- NoBo

Addie's Place: A Quiet and Quirky Private Guesthouse

Hartford
10.0 out of 10, Exceptional, (4)
"Perfect size and location! "
United States
Lyn H.
$180 nightly
The price is $203
Nov 16 - Nov 17
Total with taxes and fees
Addie's Place: A Quiet and Quirky Private Guesthouse

2 Queens | 10 Mins to the Mountains | Foliage

Bridgewater
8.8 out of 10, Excellent, (5)
"We really loved the location because we wanted to be close to Bridgewater Corners where our son just purchased a property. We loved the “Two Queens” unit and appreciated all the attention to detail with kitchen appliances, separate entrance, covered deck, available parking and very nicely landscaped side yard. Hoping to be able to stay there again this fall when we come back to VT to visit family and experience the VT fall season. Location made it so easy to go to many fun restaurants from the...
United States
Anonymous traveler
$177 nightly
The price is $194
Nov 16 - Nov 17
Total with taxes and fees
2 Queens | 10 Mins to the Mountains | Foliage

Efficient condo near slopes with kitchenette & great location

Ludlow
8.6 out of 10, Excellent, (32)
"Stay was good. Couldn’t figure out the TV - Not sure if there was actually cable or not. Close to the main road so traffic was a bit loud. Other than that great stay. "
United States
Michael
$176 nightly
The price is $199
Nov 17 - Nov 18
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$224 nightly
The price is $253
Nov 16 - Nov 17
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ludlow
8.6 out of 10, Excellent, (4)
"Clean room. Glad that the text responses are quick. We weren't initially provided a room number and then the door code we were given would not work. Host responded and was able to reset code from afar. "
United States
Ana Maria C.
$209 nightly
The price is $237
Nov 17 - Nov 18
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Ludlow
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
$228 nightly
The price is $258
Nov 17 - Nov 18
Total with taxes and fees
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"The room was really cozy and the community area was quaint and comfortable. "
United States
Bethany
$130 nightly
The price is $146
Nov 16 - Nov 17
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn

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

Ludlow
10.0 out of 10, Exceptional, (102)
"Pretty nice little condo in a nice location."
United States
jonathan H.
$260 nightly
The price is $281
Nov 17 - Nov 18
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge
10.0 out of 10, Exceptional, (4)
"The Gnome Home was everything we hoped for and more. The hosts are so helpful with communication, especially when a hefty snow storm hit. The home is cozy, clean and very well stocked with everything you need."
United States
Leah S.
$487 nightly
The price is $514
Nov 18 - Nov 19
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Ludlow
9.0 out of 10, Wonderful, (14)
"The location was awesome. Close to amenities and local eateries. Too close to the road for my preference. Road noise from the traffic was constant. The ki g size bed was amazing and very comfortable."
United States
Donna H.
$233 nightly
The price is $263
Nov 17 - Nov 18
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

3.0 star property
Okemo Village
10.0 out of 10, Exceptional, (5)
"We loved that we could ski right out the back door. The house was clean, comfortable. The owner was very responsive. We will definitely consider staying here again. "
United States
John O.
$348 nightly
The price is $393
Nov 24 - Nov 25
Total with taxes and fees
Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Ludlow
9.0 out of 10, Wonderful, (22)
"This modest property was super clean and convenient to Okemo ski resort. Access was simple as the door codes were emailed. I do wish there was an interior deadbolt/chain-lock for security in addition to just the exterior access combo.This whole unit was freshly painted. The all purpose room was spacious. The kitchen corner was modestly equipped but offered the necessities. The couch was comfortable and the TV was average. The bathroom was spacious but had a dated floor and shower. The...
United States
John
$209 nightly
The price is $237
Nov 17 - Nov 18
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Clock Tower Base Area
8.4 out of 10, Very Good, (13)
"Excellent Location.. "
United States
Juan Carlos L.
$275 nightly
The price is $310
Nov 20 - Nov 21
Total with taxes and fees
Ski-in/out mountainside condo with balcony, washer/dryer & high-speed WiFi

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater
9.4 out of 10, Exceptional, (16)
"It was a great location for what we were looking to do. Great size and we loved the hot tub. Very comfortable. We enjoyed our stay and would come again"
United States
Ashley G.
$438 nightly
The price is $491
Nov 16 - Nov 17
Total with taxes and fees
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

2.0 star property
Plymouth
$476 nightly
The price is $533
Nov 19 - Nov 20
Total with taxes and fees
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Clock Tower Base Area
9.2 out of 10, Wonderful, (25)
"My sister and our two sons stayed here. It was simple, and extraordinarily convenient . It could use some updating - namely the pull out sofa mattress - labeled from 1992. Not comfortable. Besides that, it was right for the price if convenience is a priority."
United States
Justin B.
$197 nightly
The price is $222
Nov 17 - Nov 18
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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 County Hotel Reviews

Find out more about Windsor County

Discover your perfect Windsor County vacation rental with Expedia

How many vacation rentals are available in Windsor County?


Expedia has plenty of vacation rentals to choose from in and around  Windsor County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Windsor County?


The selection of Windsor County vacation rentals we have selected for you start as low as $187 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Windsor County?


Vacation rentals in Windsor County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windsor County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Windsor County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Windsor County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Windsor County?


Find vacation rentals in Windsor County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windsor County.  


What amenities are available in a vacation rental in Windsor County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Windsor County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Windsor County?   


Everytime is a great time to head to Windsor County! Staying in a Windsor County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windsor County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windsor County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windsor County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Windsor County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.