Windham County Vacation Rentals

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Top cities in Windham County

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

Brattleboro

Windham County Vacation Rentals

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow

$262 nightly
The price is $296 total per night
$296 total
Aug 26 - Aug 27
Total includes taxes and fees
Guests staying at this condo enjoy features like ski-in/ski-out access.
Kitchen
Parking available
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!

$502 nightly
The price is $567 total per night
$567 total
Aug 21 - Aug 22
Total includes taxes and fees
A sauna and a hot tub are featured at this cabin.
Hot Tub
Kitchen
Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
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

$247 nightly
The price is $279 total per night
$279 total
Aug 24 - Aug 25
Total includes taxes and fees
At this condo, guests enjoy ski-in/ski-out access, an indoor pool, and a gym. This ski condo building also has laundry facilities.
Pool
Kitchen
Seasons On Mount Snow - Ski-in/Ski-out

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

This condo features ski-in/ski-out access, an indoor pool, and a gym. Other amenities at this ski condo building include a sauna, a hot tub, and laundry facilities.
Pool
Hot Tub
Londonderry Chalet w/ Deck, Fire Pit & Views!

Londonderry Chalet w/ Deck, Fire Pit & Views!

This cabin features free WiFi in public areas and laundry facilities.
Kitchen
Washer
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

Guests of this condo enjoy features like a gym, a sauna, and laundry facilities.
Pool
Kitchen
Jacksonville Cabin w/ Wraparound Deck & Views

Jacksonville Cabin w/ Wraparound Deck & Views

Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
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

$220 nightly
The price is $249 total per night
$249 total
Aug 24 - Aug 25
Total includes taxes and fees
At this vacation home, guests have access to a gym, a sauna, and a hot tub. This vacation home also has laundry facilities.
Pool
Hot Tub
Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

2 out of 5
This apartment is a smoke-free apartment building.
Kitchen
Air conditioning
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd, Stratton, VT
$380 nightly
The price is $429 total per night
$429 total
Aug 21 - Aug 22
Total includes taxes and fees
Long Trail House at Stratton Mountain Resort features a golf course, an outdoor pool, and a gym. Free parking is included with your stay. Front-desk staff can answer questions 24/7, and assist with securing valuables, concierge services, and access to locker space. Other amenities at this ski aparthotel include a sauna, outdoor tennis courts, and indoor tennis courts.
Pool
Hot Tub
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

$326 nightly
The price is $365 total per night
$365 total
Aug 25 - Aug 26
Total includes taxes and fees
Guests staying at this cabin have access to barbecue grills and a garden.
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

Guests staying at this vacation home enjoy an outdoor pool, an arcade/game room, and laundry facilities. Other amenities at this family-friendly vacation home include barbecue grills and a garden.
Pool
Kitchen
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.

Guests staying at this vacation home enjoy access to ski-in/ski-out access, an outdoor pool, and a sauna. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this ski vacation home include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
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!

Guests staying at this vacation home enjoy an indoor pool, a sauna, and a hot tub. Other amenities at this family-friendly vacation home include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Charming 1-bedroom condo in delightful Dover

Charming 1-bedroom condo in delightful Dover

$179 nightly
The price is $202 total per night
$202 total
Sep 3 - Sep 4
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a water dispenser.
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

$767 nightly
The price is $866 total per night
$866 total
Aug 21 - Aug 22
Total includes taxes and fees
Guests of this vacation home have access to an indoor pool, a gym, and a hot tub. This vacation home also has laundry facilities.
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

$256 nightly
The price is $287 total per night
$287 total
Sep 6 - Sep 7
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
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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.

Hotel Options in Windham County

    The Putney Inn

    The Putney Inn

    57 Putney Landing Rd, Putney, VT
    $138 nightly
    The price is $151 total per night from Aug 24 to Aug 25
    $151 total
    Aug 24 - Aug 25
    Total includes taxes and fees
    8.4/10 Very Good! (1,000 reviews)
    Hampton Inn Brattleboro

    Hampton Inn Brattleboro

    1378 Putney Road, Brattleboro, VT
    $122 nightly
    The price is $135 total per night from Sep 2 to Sep 3
    $135 total
    Sep 2 - Sep 3
    Total includes taxes and fees
    8/10 Very Good! (866 reviews)
    Colonial Motel And Spa

    Colonial Motel And Spa

    889 Putney Rd, Brattleboro, VT
    $140 nightly
    The price is $154 total per night from Aug 21 to Aug 22
    $154 total
    Aug 21 - Aug 22
    Total includes taxes and fees
    6.6/10 (1,000 reviews)

Orbitz makes it easy to find vacation rentals in Windham County 

🏠 What is the best price for a Windham County vacation rental?


Windham County rentals range between $135 and $866 per night. At Orbitz, we have a vacation rental for every budget.


🏠 What types of vacation rentals in Windham County can I rent?


Choose from apartments to beautifully decorated vacation homes, condo resorts or even B&Bs or motels for your next Windham County getaway. Orbitz filters your search results so you can find the best Windham County vacation rental for you. We have tons of options.


🏠 Are cancellations free on Windham County vacation rentals with Orbitz?


You may be able to cancel or amend your Windham County vacation rental booking free of charge before a pre-agreed deadline. Make sure to check the terms of cancellation before you book—so you know exactly where you stand. 


🏠 How do I find the best vacation rental deals in Windham County?


Enter your travel dates, and we’ll do the rest. You can then browse our exciting deals and all the tempting vacation rentals we have on offer in Windham County by filtering your search by amenities, prices, and property types and look at customers ratings to help you pick.


🏠 How do I cancel my vacation rental booking through Orbitz


Vacation rentals have slightly different rules to other bookings on Orbitz. Usually, you need to contact your property manager, you may be able to get a full refund before the cancellation date. Click My TripsOpens in a new window on your Orbitz account page to find the right information contact. If you need more help, visit our Customer ServiceOpens in a new window page. 


🏠 What are the advantages of booking a vacation rental in Windham County?


When you book a Windham County vacation rental, you have the privacy of home and can add on those luxury amenities of a hotel. Filter your vacation rental results to find a place with a hot tub or pool, games rooms or large patio with a barbecue. With so much choice on offer, it’s easy to plan the perfect trip with Orbitz. 


🏠 Where can I find vacation rentals in Windham County?


Escape back to nature and check out some of the smaller towns. You’ll find great vacation rentals right across Windham County—with plenty of hidden gems. We also have plenty of inventory in Windham County main cities and near popular attraction spots.


🏠 Why should I book my Windham County vacation rental with Orbitz?


At Orbitz, we search the market for the best accommodation, flights, and car rental deals, so you don’t have to. We’ll help you build your dream Windham County vacation. With plenty of vacation rentals on offer, you can be sure to find the one that’s right for you in just a few clicks. 


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