Vacation rentals in Windham County

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Top cities to explore in Windham County

Mount Snow showing mountain biking as well as an individual male

West Dover

Vacation Rentals
West Dover

Top vacation rentals in Windham County

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

15.8 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
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

16.1 mi from city center
$327 nightly
The price is $366 total per night
$366 total
Jun 5 - Jun 6
Total includes taxes and fees
This cabin features a garden, laundry facilities, and barbecue grills.
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

8.05 mi from city center
$305 nightly
The price is $342 total per night
$342 total
Jun 5 - Jun 6
Total includes taxes and fees
This vacation home features laundry facilities.
Kitchen
Washer
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
$354 nightly
The price is $400 total per night
$400 total
Jun 10 - Jun 11
Total includes 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
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

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.
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Indoor Pool, Golf, Hike, Relax!

10.16 mi from city center
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An indoor pool is featured at this vacation home, along with laundry facilities and barbecue grills.
Pool
Kitchen
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

11.43 mi from city center
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This vacation home features an indoor pool and a hot tub. There's a sauna 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

15.16 mi from city center
$247 nightly
The price is $279 total per night
$279 total
Jun 6 - Jun 7
Total includes 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.
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

7.46 mi from city center
$182 nightly
The price is $206 total per night
$206 total
Jun 5 - Jun 6
Total includes taxes and fees
Stay at this apartment in East Dover. Enjoy an in-room coffeemaker. Popular attractions Dover Common and Dover Free Library are located nearby.
Kitchen
Mountain view
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

15.3 mi from city center
$219 nightly
The price is $247 total per night
$247 total
Jun 7 - Jun 8
Total includes taxes and fees
This vacation home features a gym and a hot tub. A sauna and laundry facilities are also provided.
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

11.27 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

12.14 mi from city center
$378 nightly
The price is $427 total per night
$427 total
Jun 5 - Jun 6
Total includes taxes and fees
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free vacation home. There's a gym on site, and laundry facilities and barbecue grills are also offered.
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

11.94 mi from city center
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This vacation home features an indoor pool and a gym. 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 barbecue grills.
Bright three-level home with water views, jetted tub, firepit, and pool table

Bright three-level home with water views, jetted tub, firepit, and pool table

15.29 mi from city center
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This vacation home includes a garden and laundry facilities.
Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

Deerwood Hill ~ après ski cabin • hot tub • fire pit • Stratton • Manchester

15.68 mi from city center
$495 nightly
The price is $559 total per night
$559 total
Jun 5 - Jun 6
Total includes taxes and fees
A hot tub is featured at this cabin, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
Hot Tub
Kitchen
Hike & Swim On-Site: Cozy Falls Brook Cabin

Hike & Swim On-Site: Cozy Falls Brook Cabin

3.09 mi from city center
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This cabin features a garden, laundry facilities, and barbecue grills.
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful River Retreat

15.7 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Rustic, dog-friendly escape with private pool, sweeping views, & W/D

Rustic, dog-friendly escape with private pool, sweeping views, & W/D

8.06 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
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 $206 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.