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

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 lodge includes a garden and laundry facilities.
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
$349 nightly
The price is $395 total per night
$395 total
Nov 3 - Nov 4
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.
Long Trail House Studio at Stratton Mountain Resort

Long Trail House Studio at Stratton Mountain Resort

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.
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

15.34 mi from city center
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This condo features an outdoor pool and a hot tub. There's a sauna on site, and laundry facilities and concierge services are also offered.
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
$249 nightly
The price is $282 total per night
$282 total
Oct 6 - Oct 7
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.
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

14.93 mi from city center
$502 nightly
The price is $567 total per night
$567 total
Oct 13 - Oct 14
Total with taxes and fees
This cabin features a hot tub and a sauna.
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

16.1 mi from city center
$330 nightly
The price is $370 total per night
$370 total
Oct 6 - Oct 7
Total with taxes and fees
This cabin includes a garden and barbecue grills.
The Green Mountain Chapel // Old Church repositioned into 3 BR

The Green Mountain Chapel // Old Church repositioned into 3 BR

2 out of 5
18.25 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
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.

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.
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.
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio

15.3 mi from city center
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This condo features an outdoor pool and a gym. There's a hot tub on site, and laundry facilities and barbecue grills are also offered.
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

18.95 mi from city center
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This vacation home features a garden, laundry facilities, and barbecue grills.
Treetop townhouse with Hot Tub and plenty of space for the whole family!

Treetop townhouse with Hot Tub and plenty of space for the whole family!

14.79 mi from city center
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A hot tub is featured at this vacation home, along with laundry facilities and barbecue grills.
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

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.
Spacious Riverfront Home 7 Minutes to Stratton!

Spacious Riverfront Home 7 Minutes to Stratton!

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.
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

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

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

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.
Charming 1-bedroom condo in delightful Dover

Charming 1-bedroom condo in delightful Dover

11.44 mi from city center
$179 nightly
The price is $202 total per night
$202 total
Oct 14 - Oct 15
Total with taxes and fees
This vacation home features laundry facilities.
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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 $202 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.