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Vacation Rentals in Windsor County

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Top Cities in Windsor County

Top Vacation Rentals in Windsor County

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

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$244 nightly
The price is $276
Dec 16 - Dec 17
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

The Cabin that brings people together

Bridgewater
9.6 out of 10, Exceptional, (82)
"This was our 3rd visit for an annual family reunion. Nice house with great space, and the yard is a great space to really spread out. The manager is very responsive and checks in periodically; they really want you to have a great stay. I highly recommend this vacation rental, and we’ll be back!"
United States
Peter L.
The Cabin that brings people together

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
8.0 out of 10, Very Good, (41)
"Plenty of space and the two living rooms are great because the upstairs living room is very small."
United States
Brad H.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Weston
9.8 out of 10, Exceptional, (9)
"An absolutely incredible home and property for a week long end of summer vacation. The setting, atmosphere, decor and attention to detail were all top notch and we couldn’t have been happier. We particularly loved the layout and all of the amenities. This property is a true winner for any season, and we cannot wait to return for a winter retreat! "
United States
Chris L.
Charming mountain retreat with pool, fire pit, glamping loft, and endless views

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

Cavendish
10.0 out of 10, Exceptional, (30)
"Beautiful property and excellent accommodations"
United States
Anthony W.
$320 nightly
The price is $349
Dec 9 - Dec 10
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

Ludlow
10.0 out of 10, Exceptional, (35)
"The condo is beautiful, the beds were comfortable, and the community is quiet. We loved having the pool and gym to use during our stay. The proximity to downtown Ludlow, Okemo Clocktower and Jackson Gore, Camp Plymouth, and the Green Mountain Sugar House is ideal. We very much enjoyed our time here and would come back again. "
United States
Beth L.
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
$171 nightly
The price is $187
Dec 10 - Dec 11
Total with taxes and fees
Treehouse at Wise Pines- NoBo

Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger

West Windsor
Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
9.8 out of 10, Exceptional, (128)
"Beautiful place! Enjoyed our stay!"
United States
Cathy B.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Idyllic Lakefront House Suited Two Families

Ludlow
9.6 out of 10, Exceptional, (171)
"House and grounds were well maintained. "
United States
Dorothy Y.
Idyllic Lakefront House Suited Two Families

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Ludlow
9.8 out of 10, Exceptional, (181)
"Great stay, for a golf trip with 12 guys, there was plenty of room for everyone, would definitely recommend and will be trying to come back and stay as well!"
United States
Matt C.
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Ludlow
9.4 out of 10, Exceptional, (41)
"Lovely property and great location to outdoor activities."
United States
Ellen C.
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Ludlow
9.6 out of 10, Exceptional, (19)
"The house, its location, and dock are real nice. Would come here again."
United States
Wendy G.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Solitude Village at Okemo

4.0 star property
Clock Tower Base Area
8.0 out of 10, Very Good, (32)
"Great location!"
United States
DIEN
Solitude Village at Okemo

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
$171 nightly
The price is $187
Dec 8 - Dec 9
Total with taxes and fees
Treehouse at Wise Pines- SoBo

Chester Farmhouse Ski Retreat near Slopes

Chester Depot
9.6 out of 10, Exceptional, (16)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$299 nightly
The price is $335
Dec 9 - Dec 10
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock
9.8 out of 10, Exceptional, (228)
"Lovely property. Peaceful and beautiful surroundings."
United States
Karen G.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock Village Carriage House

Woodstock
9.8 out of 10, Exceptional, (102)
"Nice location, walking distance from the center of town. "
United States
Jack W.
Woodstock Village Carriage House

King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths

Bethel
10.0 out of 10, Exceptional, (64)
"Very cozy, warm and inviting. Beds were all comfortable. House is big enough to have your own space yet intimate enough for pool, and family game night. Highly recommend!"
United States
Christine F.
King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths

Luxe Quechee home on quiet road - chef’s kitchen, two-car garage, screened porch

Quechee
8.4 out of 10, Very Good, (21)
"Check that stove and washing machine work before booking"
United States
Delia O.
Luxe Quechee home on quiet road - chef’s kitchen, two-car garage, screened porch
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.