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Vacation Rentals in Windham County

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Top Cities in Windham County

Our top choices for Windham County vacation rentals

3.0 star property
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
$424 nightly
The price is $479
Dec 16 - Dec 17
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
8.0 out of 10, Very Good, (2)
"Place was amazing! Beautiful property and so unique. Being pet friendly was a huge plus! We had a wonderful time!"
United States
Alexia R.
$1,087 nightly
The price is $1,228
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
10.0 out of 10, Exceptional, (11)
"Beautiful new home, great for big family and friend groups. Comfortable bedding and furniture. Lots of open space and seating "
United States
Gena L.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
8.6 out of 10, Excellent, (8)
"We had a wonderful stay."
United States
Joshua
$502 nightly
The price is $567
Dec 16 - Dec 17
Total with taxes and fees
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
9.8 out of 10, Exceptional, (48)
"Overall a nice stay, thanks Jen!"
United States
Anonymous traveler
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
9.4 out of 10, Exceptional, (68)
"This studio apartment is cozy and comfortable, with a balcony offering great views. The kitchen is clean and functional, and indoor parking is very convenient."
United States
GO PIN
Stratton South Long Trail Studio Adjacent to the Village and Lifts
10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
$1,228 nightly
The price is $1,387
Dec 16 - Dec 17
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
8.6 out of 10, Excellent, (27)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
$385 nightly
The price is $435
Jan 12 - Jan 13, 2026
Total with taxes and fees
Lovely ski-in/out condo steps from ski lift with trails and amazing views
9.4 out of 10, Exceptional, (29)
"This place is enormous with nooks and crannies everywhere to get away, shoot pool, play video games, read, swim, sit in the sauna,barbecue, or wade in the brook below! Some of the rooms are great for a couple, others are better for a bunch of kids who are willing to sleep in a bunk or twin bed. "
United States
khs
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.8 out of 10, Exceptional, (36)
"We loved our stay! Such lovely cabin! We loved it so much that we were bummed we didn’t book a longer stay. It had everything we needed to make our stay comfortable."
United States
Boris P.
VT Cabin overlooking the West River and Village
10.0 out of 10, Exceptional, (62)
"Another great summer vacation with family at this beautiful property! Have already booked for next year."
United States
Shirlee B.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
8.2 out of 10, Very Good, (10)
"Lovely place for a large group of people."
United States
Nicole M.
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$247 nightly
The price is $280
Jan 7 - Jan 8, 2026
Total with taxes and fees
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
10.0 out of 10, Exceptional, (11)
"Great time and perfect locationEverything you need for a Stratton get away"
United States
Anthony R.
Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!
10.0 out of 10, Exceptional, (7)
LUX property, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV
10.0 out of 10, Exceptional, (64)
"Beautiful rural location next to the Green River. A peaceful relaxing place to stay. We would love to stay here again "
United States
Georgene M.
The Jelly Mill-A Peaceful River Retreat
10.0 out of 10, Exceptional, (65)
"Was a great short getaway. Place is clean and pool was great. Would recommend "
United States
Christopher M.
Long Trail House Studio at Stratton Mountain Resort
9.6 out of 10, Exceptional, (55)
"Great, clean condo right near the village. It was a really nice place to stay and a good for a family of 4."
United States
David S.
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$330 nightly
The price is $370
Dec 23 - Dec 24
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.0 out of 10, Wonderful, (10)
"Very private an comfortable. Wish i could buy the place!"
United States
Tyler C.
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK
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 Windham County Hotel Reviews

Find out more about Windham County

Discover your perfect Windham County vacation rental with Expedia

How many vacation rentals are available in Windham County?


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


How much is a vacation rental in Windham County?


The selection of Windham County vacation rentals we have selected for you start as low as $280 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 Windham County?


Vacation rentals in Windham 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 Windham County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Windham 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 Windham 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 Windham County?


Find vacation rentals in Windham 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 Windham County.  


What amenities are available in a vacation rental in Windham 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 Windham County vacation rentals designed to suit every budget and trip type.


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


Everytime is a great time to head to Windham County! Staying in a Windham 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 Windham 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 Windham County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windham County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Windham 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.