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
$433 nightly
The price is $489 total per night
$489 total
Mar 24 - Mar 25
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
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Dover VT
9.9 mi from city center
$450 nightly
The price is $509 total per night
$509 total
Feb 26 - Feb 27
Total with taxes and fees
This campground features a hot tub and a sauna. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden and laundry facilities are also provided.
Hot Tub
Kitchen
Weekday Special ⛷️Stratton Slopeside Condo at The Landmark!🎿

Weekday Special ⛷️Stratton Slopeside Condo at The Landmark!🎿

Stratton VT
15.42 mi from city center
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This condo features ski-in/ski-out access and laundry facilities.
Kitchen
Washer
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro VT
10.23 mi from city center
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This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the sauna and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Dover VT
12.1 mi from city center
$320 nightly
The price is $361 total per night
$361 total
Mar 8 - Mar 9
Total with taxes and fees
Ski-in/ski-out access and a hot tub are featured at this smoke-free condo. Families will appreciate the arcade/game room and barbecue grills. A gym and a sauna are also provided.
Hot Tub
Kitchen
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend VT
4.56 mi from city center
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An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site.
Pool
Kitchen
Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna

Windham VT
14.13 mi from city center
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Ski-in/ski-out access and an outdoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and conveniences like a garden and concierge services.
Pool
Hot Tub
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
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
$328 nightly
The price is $367 total per night
$367 total
Feb 26 - Feb 27
Total with taxes and fees
This cabin includes a garden and barbecue grills.
Kitchen
Pet friendly
Beautiful Stratton Mountain Condo

Beautiful Stratton Mountain Condo

Stratton Mountain VT
14.91 mi from city center
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This condo features laundry facilities.
Kitchen
Washer
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

Dover VT
11.93 mi from city center
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A hot tub is featured at this condo, along with laundry facilities.
Pool
Hot Tub
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham VT
17.71 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
The Birch. Outdoor hot tub, H Pool, Theater,& More

The Birch. Outdoor hot tub, H Pool, Theater,& More

Dover VT
11.94 mi from city center
$335 nightly
The price is $379 total per night
$379 total
Mar 18 - Mar 19
Total with taxes and fees
This villa features an indoor pool and a gym. Enjoy the hot tub and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

Cabin-7 minutes to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dog OK

2 out of 5
Jamaica VT
11.57 mi from city center
$166 nightly
The price is $188 total per night
$188 total
Feb 26 - Feb 27
Total with taxes and fees
This cabin features barbecue grills.
Kitchen
Pet friendly
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
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
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT
12.86 mi from city center
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This vacation home includes a garden and laundry facilities.
Kitchen
Washer
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Dover VT
12.31 mi from city center
$280 nightly
The price is $317 total per night
$317 total
Mar 23 - Mar 24
Total with taxes and fees
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free apartment. A gym is also provided.
Pool
Kitchen
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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 $188 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.