Vacation rentals in Windham County

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Top cities to explore in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!

Brattleboro

Vacation Rentals
Brattleboro

Top vacation rentals in Windham County

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
15.34 mi from city center
$366 nightly
The price is $413 total per night
$413 total
Nov 25 - Nov 26
Total with taxes and fees
A golf course, 10 restaurants, and 2 indoor tennis courts are all featured at this smoke-free aparthotel. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas.
Pool
Hot Tub
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Cozy 2-bedroom cabin near Mount Snow 3 min drive

2 out of 5
Dover VT
11.36 mi from city center
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This cabin features laundry facilities.
Kitchen
Washer
Seasons On Mount Snow - Ski-in/Ski-out

Seasons On Mount Snow - Ski-in/Ski-out

Dover VT
12.12 mi from city center
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Ski-in/ski-out access and an indoor pool are featured at this smoke-free condo. There's a gym on site, and laundry facilities and barbecue grills are also offered.
Pool
Hot Tub
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Stratton VT
15.16 mi from city center
$255 nightly
The price is $288 total per night
$288 total
Nov 23 - Nov 24
Total with taxes and fees
Ski-in/ski-out access and an indoor pool are featured at this smoke-free condo. A gym and laundry facilities are also provided.
Pool
Kitchen
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover VT
11.88 mi from city center
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This vacation home features ski-in/ski-out access, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
Kitchen
Washer
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend VT
2.88 mi from city center
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This vacation home includes a garden and laundry facilities.
Washer
Dryer
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton VT
16.1 mi from city center
$327 nightly
The price is $366 total per night
$366 total
Nov 20 - Nov 21
Total with taxes and fees
This cabin includes a garden and barbecue grills.
Kitchen
Pet friendly
Ski on ski off condo

Ski on ski off condo

Stratton VT
15.14 mi from city center
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This condo features laundry facilities.
Kitchen
Washer
Long Trail House Studio at Stratton Mountain Resort

Long Trail House Studio at Stratton Mountain Resort

Stratton VT
15.34 mi from city center
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This apartment features a hot tub and a sauna. Laundry facilities are provided for your convenience.
Pool
Hot Tub
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

West Dover Vermont VT
12.07 mi from city center
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This vacation home features a hot tub and a sauna. Families will appreciate the arcade/game room and onsite laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Spacious Riverfront Home 7 Minutes to Stratton!

Spacious Riverfront Home 7 Minutes to Stratton!

Jamaica VT
11.31 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Hot Tub
Kitchen
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover VT
11.94 mi from city center
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Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. A garden and laundry facilities are also provided.
Hot Tub
Kitchen
Mountain & sunset views from balcony! Heated pool/spas, walk to lifts & village!

Mountain & sunset views from balcony! Heated pool/spas, walk to lifts & village!

Stratton VT
15.35 mi from city center
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An outdoor pool is featured at this condo, along with laundry facilities.
Pool
Kitchen
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Jamaica VT
12.38 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Extraordinary Stratton Ski On/Ski Off Home

Extraordinary Stratton Ski On/Ski Off Home

15.02 mi from city center
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Ski-in/ski-out access and a hot tub are featured at this smoke-free vacation home. Laundry facilities are provided for your convenience.
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Whitingham VT
17.78 mi from city center
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A hot tub is featured at this vacation home, along with a garden.
Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball

Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball

Stratton VT
16.07 mi from city center
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A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!

This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!

Halifax VT
17.31 mi from city center
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This cabin features a garden, laundry facilities, and barbecue grills.
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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.

The Best Way to Find Vacation Rentals in Windham County 

How cheap is a vacation rental in Windham County?


You can find Windham County vacation rentals from just $288 per night. 


How do you look for the best vacation rental deals in Windham County with Travelocity?


Simply enter your travel dates and filter by price, property type, bedrooms, amenities, and more. We put all the best deals in one place, so it’s easy to find your perfect stay. You’ll always find incredible deals on Windham County vacation rentals with Travelocity. 


Are cancellations free on vacation rentals with Travelocity?


You may be able to cancel your Windham County vacation rental for free. Cancellation policies differ between properties so check the terms of your stay before you book. Travelocity offers many flexible cancellation options as well as book now, pay later deals for peace of mind.


What types of vacation rentals are available in Windham County?


Whether you’re in search of adventure, planning a romantic getaway, or booking a trip for the whole family, you’re sure to find the perfect Windham County vacation rental. Check out our tempting selection of resorts, apartments, vacation homes, condos and more and start building a trip to really look forward to, whatever your budget and your wish list.


What are the benefits of booking a short-term rental in Windham County?


Whether you’re a winter wanderer or planning a summer sojourn, Windham County vacation rentals make for a great trip—find one at Travelocity for a fantastic price. With a range of amenities on offer, like swimming-pools, free WiFi, breakfast included, pet-friendly options and many more, it’s easy to book a vacation rental that checks all the boxes. And with Travelocity’s easy filtering system, you’ll find yours in no time. 


Where can I find vacation rentals in Windham County?


Take your pick from the excitement of the big Windham County cities. Or escape to nature in the miles of greenery that are waiting for you. Browse a selection of the best deals with Travelocity, enter your travel dates, or check out the map view to find a hidden gem. 


How do I find a family-friendly vacation rental in Windham County?


Simply enter your travel dates and hit search. From here, you can filter to find your family-friendly stay, as well as a range of other amenities, such as hot tubs, pools, and even waterparks. 


Why is Travelocity the best site to find your Windham County rentals?


Travelocity takes care of everything, bringing incredible deals on an impressive selection of accommodation into one simple-to-use portal. And because we always source incredible deals, you can make a saving on many bookings. Travelocity makes it easy.


How do I cancel my vacation rental with Travelocity?


It’s simple. Just contact the property manager. You’ll find their contact information in the itinerary section of your Travelocity account. In many cases, you may be able to get a full refund if you cancel before the cancellation deadline. Deadlines differ between properties, so it’s always best to check before you book. To find out more, visit the Customer Service PortalOpens in a new window.