Windham County Vacation Rentals

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Top cities in Windham County

Mount Snow
Vacation RentalsVacation Rentals
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West Dover

West Dover

Windham County Vacation Rentals

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
$342 nightly
The price is $386 total per night
$386 total
Jun 22 - Jun 23
Total with 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 concierge services, securing valuables, and access to locker space. Other amenities at this ski aparthotel include a sauna, outdoor tennis courts, and indoor tennis courts.
Pool
Hot Tub
Seasons On Mount Snow - Ski-in/Ski-out

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

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

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

Whitingham VT
This vacation home features a hot tub and a garden.
Hot Tub
Kitchen
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton VT
$323 nightly
The price is $362 total per night
$362 total
Jun 17 - Jun 18
Total with taxes and fees
Guests staying at this cabin have access to barbecue grills and a garden.
Kitchen
Pet friendly
Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Starry Skies: 7min to SkiStratton+PikesFalls+DogOK

Jamaica VT
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
Cabin Retreat in Southern Vermont

Cabin Retreat in Southern Vermont

Putney VT
This cabin features a hot tub and barbecue grills.
Hot Tub
Kitchen
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Townshend VT
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
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
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
The Mahogany. House near Mt Snow | Hot Tub | Pool

The Mahogany. House near Mt Snow | Hot Tub | Pool

Dover VT
At this villa, guests enjoy features like an indoor pool, a gym, and a sauna. Other amenities at this family-friendly villa include a hot tub, an arcade/game room, and barbecue grills.
Pool
Hot Tub
Long Trail House Studio at Stratton Mountain Resort

Long Trail House Studio at Stratton Mountain Resort

Stratton VT
At this apartment, guests have access to a sauna, a hot tub, and laundry facilities.
Pool
Hot Tub
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
At this condo, guests have access to a hot tub and laundry facilities.
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

Wardsboro VT
Guests staying at this vacation home enjoy a gym, a sauna, and a hot tub. Other amenities at this golf vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Pool
Hot Tub
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
Guests staying at this vacation home enjoy ski-in/ski-out access, a hot tub, and laundry facilities. This ski vacation home also has a garden.
Hot Tub
Kitchen
4 BR Mt Snow Okemo Ski Chalet w Amazing views!

4 BR Mt Snow Okemo Ski Chalet w Amazing views!

Brattleboro VT
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Washer
Spacious Corner Townhouse from Mt. Snow! Private hot tub!

Spacious Corner Townhouse from Mt. Snow! Private hot tub!

Dover VT
Guests of this vacation home have access to an indoor pool, a gym, and a hot tub. Additional amenities include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Hot Tub
Stratton Mountain Long Trail House panoramic MOUNTAIN VIEW

Stratton Mountain Long Trail House panoramic MOUNTAIN VIEW

Stratton VT
This condo offers a gym, a sauna, and a hot tub. Other amenities at this adults-only condo building include laundry facilities and barbecue grills.
Pool
Hot Tub
Perfect for family getaway, across from Mount Snow Mountain- Sleeps up to 12!

Perfect for family getaway, across from Mount Snow Mountain- Sleeps up to 12!

Dover VT
At this condo, guests enjoy an indoor pool, a gym, and a sauna. Additional amenities include a hot tub, laundry facilities, and a garden.
Pool
Hot Tub
Everything you need - swim, relax, play outside!

Everything you need - swim, relax, play outside!

Londonderry VT
Guests staying at this vacation home enjoy an indoor pool, an arcade/game room, and laundry facilities. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this family-friendly vacation home include local meal delivery service, barbecue grills, and a garden.
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.

Hotel Options in Windham County

    Latchis Hotel

    Latchis Hotel

    50 Main Street Brattleboro VT
    $138 nightly
    The price is $152 total per night from Jun 22 to Jun 23
    $152 total
    Jun 22 - Jun 23
    Total with taxes and fees
    8.6/10 Excellent! (902 reviews)
    Grand Summit Resort, A Vail Resorts Property

    Grand Summit Resort, A Vail Resorts Property

    89 Grand Summit Way West Dover VT
    $158 nightly
    The price is $174 total per night from Jul 15 to Jul 16
    $174 total
    Jul 15 - Jul 16
    Total with taxes and fees
    8.6/10 Excellent! (274 reviews)
    Hampton Inn Brattleboro

    Hampton Inn Brattleboro

    1378 Putney Road Brattleboro VT
    $111 nightly
    The price is $122 total per night from Jul 2 to Jul 3
    $122 total
    Jul 2 - Jul 3
    Total with taxes and fees
    8.2/10 Very Good! (995 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 $122 and $386 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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