Windham Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

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, (167 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
The price is ￥26,782
￥55,757 total
includes taxes & fees
Apr 7 - Apr 8
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "
United States
Samantha R.
The price is ￥43,390
￥53,071 total
includes taxes & fees
Mar 8 - Mar 9
Owl's Nest Treehouse
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.
The price is ￥21,300
￥39,407 total
includes taxes & fees
Mar 18 - Mar 19
Wellness Getaway with a Personal Sauna, and Private River Beach!
Terrace/patio

Cabin-7 min to Ski Stratton-Wood Fired Sauna-Brook View-Woodstove-Firepit-Dog OK

Cabin-7 min to Ski Stratton-Wood Fired Sauna-Brook View-Woodstove-Firepit-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.
Cabin-7 min to Ski Stratton-Wood Fired Sauna-Brook View-Woodstove-Firepit-Dog OK
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.
The price is ￥32,290
￥39,486 total
includes taxes & fees
Mar 8 - Mar 9
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior

Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very Good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
The price is ￥22,010
￥43,594 total
includes taxes & fees
Mar 11 - Mar 12
Cozy cabin in charming Londonderry
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is ￥44,589
￥93,231 total
includes taxes & fees
Mar 9 - Mar 10
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (14 reviews)
"This was absolutely perfect. Every part of the cabin was well thought out from design to decor. We had such an amazing time and already want to plan another getaway to this place. "
United States
Adam B.
The price is ￥33,292
￥56,012 total
includes taxes & fees
Apr 7 - Apr 8
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
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.
The price is ￥19,693
￥40,406 total
includes taxes & fees
Mar 22 - Mar 23
The Studio with a View. Bring your dog, too!
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
9.2 out of 10, Wonderful, (22 reviews)
"Highly recommend clean beautiful stay!"
United States
Douglas D.
The price is ￥9,713
￥48,953 total
includes taxes & fees
Mar 23 - Mar 24
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Interior

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

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Ludlow
7.6 out of 10, Good, (56 reviews)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
United States
Warren
The price is ￥12,288
￥51,443 total
includes taxes & fees
Apr 7 - Apr 8
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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.
The price is ￥24,140
￥45,945 total
includes taxes & fees
Apr 6 - Apr 7
Family Friendly Hilltop House In Putney Vermont
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, (28 reviews)
"Overall very clean and nice. Needs some updating like more spoons, only 2, bigger coffee cups. And a new coffee table that is very worn. "
United States
David A.
The price is ￥12,307
￥41,511 total
includes taxes & fees
Apr 7 - Apr 8
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Interior

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
10.0 out of 10, Exceptional, (11 reviews)
"We enjoyed our stay."
United States
Anonymous traveler
The price is ￥35,358
￥90,945 total
includes taxes & fees
Mar 9 - Mar 10
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
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, (78 reviews)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is ￥14,179
￥44,134 total
includes taxes & fees
Apr 7 - Apr 8
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Interior

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (1 review)
"House was perfect! Well appointed with everything you need. Beds very comfortable and very clean. Host was very responsive and was there if you needed anything. Will definitely stay again. "
United States
Stephen S.
The price is ￥35,447
￥95,810 total
includes taxes & fees
Mar 9 - Mar 10
Terrific 3-bedroom cottage with AC in charming Cavendish
Property grounds

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is ￥23,036
￥63,473 total
includes taxes & fees
Mar 10 - Mar 11
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is ￥94,366
￥169,034 total
includes taxes & fees
Apr 7 - Apr 8
Cozy Vermont Cabin · Mountain Views · Near Okemo
Exterior

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Jamaica
8.0 out of 10, Very Good, (3 reviews)
"Its a cabin. Very fun for a group of friends. I wouldnt bring a family here. No running water in the morning"
United States
Hugo T.
Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Living area

Cozy Private Cabin in Andover - Fireplace & Hot tub

Cozy Private Cabin in Andover - Fireplace & Hot tub
Andover
The price is ￥34,486
￥78,148 total
includes taxes & fees
Apr 7 - Apr 8
Cozy Private Cabin in Andover - Fireplace & 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

Big Bears Lodge

Big Bears Lodge

10/10 Excellent
"Very friendly and close to the mountain "
Richard 2-night trip
Posted 17 hours ago
Big Bears Lodge

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
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Look no further and take a look at our great range of rental properties in Windham!

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 Stratton Mountain Resort and Magic Mountain Ski 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.