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)
"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

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

Ludlow
9.8 out of 10, Exceptional, (127)
"Enjoyed our stay immensely"
United States
jim m.
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

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

Ludlow
8.0 out of 10, Very Good, (41)
"This Vrbo has been housing people since the 1960's, and we're so glad to be a part of this place's history It is truly a timeless home within a beautiful area with great outdoor activites, generous people and good food (we recommend The Hatchery). Both showers (the top floor shower and the middle floor) did have a leak, but our hosts responded quickly to our concerns and addressed them within a timely manner :) "
United States
John Q.
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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!

Winterplace at Okemo

4.0 star property
Clock Tower Base Area
8.8 out of 10, Excellent, (25)
"I think it needs some wall touch ups and new shower liners , other than that is was a pleasant stay. "
United States
Jocelin
Winterplace at Okemo

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

Ludlow
9.6 out of 10, Exceptional, (19)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
United States
Kristen R.
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
Canada
Victoria M.
$171 nightly
The price is $187
Nov 14 - Nov 15
Total with taxes and fees
Treehouse at Wise Pines- SoBo

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

Ludlow
10.0 out of 10, Exceptional, (95)
"Our stay was great! Very nice cabin on the water with wood burning fireplace, fire pit, gas grill, and everything else you need for a pleasant get a way!"
United States
Jason B.
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo Mountain/Jackson Gore

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

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

Weston
9.8 out of 10, Exceptional, (8)
"If we could have given 10 stars we would have! Julia is a FANTASTIC host! Her attention to detail, thoughtfulness and care is unmeasuredThe property and house is Vermont perfection…highly reccomend🦋"
United States
Kyla S.
Charming mountain retreat with pool, fire pit, glamping loft, and endless views

Amazing home on 90 acres - AC, fireplace & great mountain views

Quechee
9.0 out of 10, Wonderful, (44)
"Enjoyed our stay immensely. Great location with a lot of privacy but still close to everything you would need."
United States
Stephen A & Jeanne L.
Amazing home on 90 acres - AC, fireplace & great mountain views

The Cabin that brings people together

Bridgewater
9.6 out of 10, Exceptional, (82)
"Everyone, including myself, couldn’t help but rave about this place!! It exceeded our expectations from top to bottom. Blown away by how perfect it was and how clean, organized and like every little detail was thought about and considered and it made our stay so comfortable and so fun!!! Definitely would come back next year for our next reunion! "
United States
Stephanie M.
The Cabin that brings people together

Converted Carriage Barn - The Carriage House Unit1

Hartford
9.6 out of 10, Exceptional, (24)
"My husband and I stayed while visiting our college-aged daughter, and she loved the place so much that she also stayed with us. Very comfortable, central location, and everything about the checkin/checkout process was seamless! 10/10"
United States
Kindra T.
Converted Carriage Barn - The Carriage House Unit1

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester
10.0 out of 10, Exceptional, (23)
"We had a really nice time staying with Paris! Cozy, quiet and beautiful! The place was clean, organized and the personal touch and accommodations made it even better. Will absolutely be back!"
United States
Anonymous traveler
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Plymouth
9.6 out of 10, Exceptional, (61)
"We were so happy with our stay. The house and surrounding area is beautiful and peaceful."
United States
Angela C.
Rustic home with a private hot tub, fireplace, cable, & washer/dryer

Nana's House

Bridgewater
10.0 out of 10, Exceptional, (47)
"Great property, lovely home, gracious hostess - what more can you ask for? Well, a beautiful setting close to Woodstock, mountain-biking, Killington all provided the backdrop for a lovely stay! Beds are quite comfortable. Love that we could bring our pups with us. Can definitely see coming back in the winter for stayover on our ski trips."
United States
Kate R.
Nana's House

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

Woodstock
9.8 out of 10, Exceptional, (226)
"All around great"
United States
Anthony g.
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Walk to Trails & Village +Pets - Highland Cabin

Woodstock
Walk to Trails & Village +Pets - Highland Cabin

Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

Barnard
9.0 out of 10, Wonderful, (12)
"Great location and beautiful setting."
United States
Peter T.
Adventure-filled getaway, ponds, trails, dog-friendly, w/d, BBQ, views & more

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

Woodstock
10.0 out of 10, Exceptional, (27)
"This property is very charming and located in an ideal spot to get around the area easily. We had a wonderful time playing games, doing puzzles, sitting in the hot tub, and exploring the river."
United States
Mary H.
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
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.