Windham Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Windham vacation rentals

Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
$325 nightly
The price is $364
May 25 - May 26
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
$271 nightly
The price is $295
May 26 - May 27
Total with taxes and fees
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Terrace/patio

Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK

Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
JAMAICA
10.0 out of 10, Exceptional, (1 review)
"Had a great couple days at the "glamping cabin." The ride to get there on a dark foggy night was a bit thrilling, but could immediately relax once I got into the cabin. Place has everything needed for a semi-primitive cabin experience. Enjoyed the sauna and thencozy bed. "
United States
Brittney C.
$140 nightly
The price is $158
May 25 - May 26
Total with taxes and fees
Cabin-Swim-Brook View-Woodfired Sauna-Firepit-Woodstove-7 min to Stratton-Dog OK
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
$255 nightly
The price is $286
May 28 - May 29
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (22 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
$310 nightly
The price is $336
Jun 1 - Jun 2
Total with taxes and fees
Owl's Nest Treehouse
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (80 reviews)
"Our stay was perfectly pleasant but the parking was far from the unit and the ski school and daycare was on a different part of the mountain which made the location inconvenient for having little kids with us."
United States
Teresa W.
$230 nightly
The price is $259
May 26 - May 27
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$197 nightly
The price is $223
May 26 - May 27
Total with taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
$287 nightly
The price is $324
May 28 - May 29
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
$247 nightly
The price is $277
May 26 - May 27
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
$180 nightly
The price is $203
May 31 - Jun 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
$287 nightly
The price is $321
May 26 - May 27
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Beach

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (51 reviews)
"Cozy place, very close to the moover and Mount Snow. Host was very responsive. Would definitely book again!"
United States
dory p.
$249 nightly
The price is $281
May 29 - May 30
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Interior

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
Stratton
7.8 out of 10, Good, (58 reviews)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
$214 nightly
The price is $241
May 26 - May 27
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$362 nightly
The price is $410
May 26 - May 27
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Children's area

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
9.6 out of 10, Exceptional, (12 reviews)
"The best stay ever!!! Very clean, great location, super cozy, all the amenities you would need. 5/5 stars, we will be coming back :)"
United States
Carolina I.
$286 nightly
The price is $323
May 25 - May 26
Total with taxes and fees
Cozy Bromley Retreat
TV

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Ludlow
9.6 out of 10, Exceptional, (18 reviews)
"Location location location!"
United States
Britt H.
$371 nightly
The price is $419
May 26 - May 27
Total with taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$294 nightly
The price is $319
May 25 - May 26
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
House (4 Bedrooms) | Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
Outdoor Adventure Hub! Family Home in West Dover
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
$310 nightly
The price is $332
May 25 - May 26
Total with taxes and fees
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
$310 nightly
The price is $332
May 25 - May 26
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
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.
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Top Windham Hotel Reviews

The Putney Inn

The Putney Inn

8/10 Good
"Property is in need of maintenance, the rooms were quite shabby, and the toilet had not been cleaned and flushed following the last persons exit. Earlier reviews mentioned burn holes in the bed covers, and these were still evident. We knew this would not be a luxury nights stay, and this reflected in the price we paid, so It suited our needs for the short time we were there."
Jackie 1-night trip
Posted 3 hours ago
The Putney Inn

Find out more about Windham

Everything you need to know about Windham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $296 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windham rentals

At Expedia, we put the best Windham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Windham?

Yes, we give you a choice of vacation rentals near the most popular points of interest in Windham, or you can select a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Windham has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: Visitors give good reviews to this Windham vacation home rental, which is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 11 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Windham?

With 12 Expedia vacation rentals, you're sure to find just the right place for your Windham stay.

What’s there to see and do in Windham?

Explore the area and family-friendly sights such as The Nature Museum, or get out into nature at a spot like Lowell Lake State Park. In the larger area, you’ll find Magic Mountain Ski Resort and Ball Mountain Dam.

What’s a vacation rental in Windham like?

Vacation rentals are private properties where you can stay for several days or longer in Windham. Vacation rentals feature amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.