Windham Vacation Rentals

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Vacation Rentals in Windham

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

Dover
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$221 nightly
The price is $250
Nov 30 - Dec 1
Total with taxes and fees
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

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

Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$224 nightly
The price is $253
Dec 1 - Dec 2
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
$227 nightly
The price is $254
Dec 4 - Dec 5
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
$149 nightly
The price is $167
Nov 30 - Dec 1
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn

Long Trail House at Stratton Mountain Resort

3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
$409 nightly
The price is $462
Dec 10 - Dec 11
Total with taxes and fees
Long Trail House at Stratton Mountain Resort

Well-appointed studio right downtown - less than a mile to Okemo Mountain

Ludlow
8.6 out of 10, Excellent, (12)
"Clean with everything we needed for a few nights stay."
United States
Sandra S.
$243 nightly
The price is $275
Dec 1 - Dec 2
Total with taxes and fees
Well-appointed studio right downtown - less than a mile to Okemo Mountain

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Ludlow
9.0 out of 10, Wonderful, (14)
"Great location and very comfortable."
United States
Richard J.
$284 nightly
The price is $321
Dec 1 - Dec 2
Total with taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$236 nightly
The price is $265
Dec 1 - Dec 2
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont

Efficient condo near slopes with kitchenette & great location

Ludlow
8.6 out of 10, Excellent, (32)
"great location, close walkto store, restaurants. Okemoabout a minute drive toparking lots. "
United States
C A.
$201 nightly
The price is $227
Dec 1 - Dec 2
Total with taxes and fees
Efficient condo near slopes with kitchenette & great location

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
$255 nightly
The price is $288
Dec 8 - Dec 9
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Cozy Bromley Retreat

Bromley Mountain
9.8 out of 10, Exceptional, (7)
"There is no place I’d rather stay in VT. It’s a perfect condo and the recent renovations are really nice. It’s got all the comforts of home and great touches throughout. Bromley is a great community to be in, it’s close to town, obviously the slopes, and just a overall stay!"
United States
Vanessa P.
$288 nightly
The price is $325
Nov 30 - Dec 1
Total with taxes and fees
Cozy Bromley Retreat

Cozy 3 bedroom condo 2.5 miles to Mount Snow

West Dover
9.0 out of 10, Wonderful, (43)
"We were unable to stay as when we went in the condo, we found the condo damp, musty, dusty, very worn, extremely outdated and uncomfortable. We left and found different accommodations for the weekend at Chateau 239 which I highly recommend. "
United States
Diana W.
$261 nightly
The price is $295
Dec 9 - Dec 10
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow

2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Ludlow
8.6 out of 10, Excellent, (4)
"Great location and convenient to all local businesses. I enjoyed it very much. Would stay here anytime and plan to again. "
United States
Kevin C.
$226 nightly
The price is $256
Dec 1 - Dec 2
Total with taxes and fees
2nd-floor downtown Ludlow studio condo with kitchenette, streaming

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Ludlow
7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
$242 nightly
The price is $273
Dec 1 - Dec 2
Total with taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Ludlow
9.0 out of 10, Wonderful, (22)
"Great rate for a place with all the basics!"
United States
Macgregor
$232 nightly
The price is $262
Dec 1 - Dec 2
Total with taxes and fees
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Ludlow
10.0 out of 10, Exceptional, (102)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
United States
Andrew L.
$264 nightly
The price is $286
Dec 1 - Dec 2
Total with taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Dover
9.8 out of 10, Exceptional, (22)
"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.
$369 nightly
The price is $417
Dec 15 - Dec 16
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (12)
"Great place . Would highly recommend it.!"
United States
Peter G.
$310 nightly
The price is $336
Nov 30 - Dec 1
Total with taxes and fees
Owl's Nest Treehouse

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
$485 nightly
The price is $543
Dec 7 - Dec 8
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

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

Walpole
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Dec 1 - Dec 2
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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

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 $253 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.

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 10 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 Mount Snow.

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.