Windham Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Windham vacation rentals

Exterior

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
10.0 out of 10, Exceptional, (2 reviews)
"The folks are SUPER and made me feel very welome"
United States
Mark
$227 nightly
The price is $254
Jan 27 - Jan 28
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
Private kitchen

Cabin in Brattleboro

The Studio with a View. Bring your dog, too!
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.
$234 nightly
The price is $262
Jan 25 - Jan 26
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Interior

Cabin in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
$324 nightly
The price is $366
Jan 26 - Jan 27
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry
Interior

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$281 nightly
The price is $306
Jan 27 - Jan 28
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Children's area

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.4 out of 10, Exceptional, (10 reviews)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
$292 nightly
The price is $330
Jan 26 - Jan 27
Total with taxes and fees
Cozy Bromley Retreat
Exterior

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (16 reviews)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
$310 nightly
The price is $336
Jan 28 - Jan 29
Total with taxes and fees
Owl's Nest Treehouse
Exterior

Cabin in Grafton

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
9.6 out of 10, Exceptional, (166 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$326 nightly
The price is $365
Feb 2 - Feb 3
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Outdoor pool, a heated pool

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.2 out of 10, Wonderful, (20 reviews)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$255 nightly
The price is $288
Jan 27 - Jan 28
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Smart TV, fireplace, Netflix, streaming services

Chalet in Dover

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.8 out of 10, Exceptional, (22 reviews)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
$430 nightly
The price is $486
Feb 10 - Feb 11
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
TV, books

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Jan 25 - Jan 26
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

Chalet in Plymouth

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
$629 nightly
The price is $704
Feb 9 - Feb 10
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Beach

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (46 reviews)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$258 nightly
The price is $292
Feb 3 - Feb 4
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds

Vacation Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (59 reviews)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$273 nightly
The price is $305
Jan 27 - Jan 28
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Exterior

Chalet in West Dover

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
10.0 out of 10, Exceptional, (21 reviews)
"Whole hearted recommend this property for anyone looking to stay in the area. Great location, great atmosphere and most importantly great house. 10/10 hidden gem. "
United States
Joshua L.
$592 nightly
The price is $669
Jan 26 - Jan 27
Total with taxes and fees
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Fridge, microwave, oven, stovetop

Chalet in Chester

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
10.0 out of 10, Exceptional, (11 reviews)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
$467 nightly
The price is $523
Jan 26 - Jan 27
Total with taxes and fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Dining

Vacation Home in Cavendish

The Dorothy-10 minutes from Okemo- freshly renovated
9.2 out of 10, Wonderful, (5 reviews)
"We had an enjoyable stay! Our hosts were very communicative and thought of the details for our stay!"
United States
Maya T.
$260 nightly
The price is $291
Jan 26 - Jan 27
Total with taxes and fees
The Dorothy-10 minutes from Okemo- freshly renovated
Terrace/patio

Chalet in Wardsboro

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
10.0 out of 10, Exceptional, (16 reviews)
"We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!"
United States
Joseph R.
$383 nightly
The price is $433
Jan 27 - Jan 28
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Lobby

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (33 reviews)
"Very nice accommodations and location!"
United States
Michael M.
$327 nightly
The price is $370
Feb 2 - Feb 3
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Exterior

Chalet in East Dover

Chalet Mount Snow/Stratton Skiing/hiking
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$475 nightly
The price is $536
Feb 4 - Feb 5
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Fridge, microwave, oven, stovetop

Chalet in Dover

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
10.0 out of 10, Exceptional, (6 reviews)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
United States
Chris I.
$523 nightly
The price is $591
Jan 26 - Jan 27
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
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 Manchester View

The Manchester View

10/10 Excellent
"Extremely clean, great views one of the best blueberry muffins I’ve ever had. Would definitely come back."
Matthew 1-night trip
Posted 2 days ago
The Manchester View

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 $257 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 Vermont Country Store, or get out into nature at a spot like Lowell Lake State Park. In the larger area, you’ll find popular places like Stratton Mountain Resort and Okemo Mountain Resort.

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.