Windham Vacation Rentals

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Check prices for these dates

In two weeks
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Windham vacation rentals

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)
"The place was very dirty. The linens were dirty, the pots/pans and all of the cooking utensils were dirty. There was a rubber band on the floor in bathroom that didn't belong to us.There was only 3 forks and a few spoons. Very little silverwear."
United States
Leigh-Ellen F.
The price is ￥8,449
￥46,784 total
includes taxes & fees
Apr 23 - Apr 24
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
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)
"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 ￥27,100
￥58,918 total
includes taxes & fees
Apr 27 - Apr 28
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (35 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is ￥25,006
￥45,960 total
includes taxes & fees
Apr 23 - Apr 24
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is ￥43,838
￥53,100 total
includes taxes & fees
Apr 27 - Apr 28
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 ￥22,317
￥41,421 total
includes taxes & fees
May 5 - May 6
Wellness Getaway with a Personal Sauna, and Private River Beach!
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)
"Perfect spot for Mount Snow "
United States
Bobby
The price is ￥9,762
￥50,120 total
includes taxes & fees
Apr 23 - Apr 24
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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, (79 reviews)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is ￥11,956
￥41,353 total
includes taxes & fees
Apr 23 - Apr 24
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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 ￥20,564
￥42,314 total
includes taxes & fees
Apr 28 - Apr 29
The Studio with a View. Bring your dog, too!
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 ￥22,668
￥43,600 total
includes taxes & fees
Apr 26 - Apr 27
Family Friendly Hilltop House In Putney Vermont
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
The price is ￥24,390
￥83,137 total
includes taxes & fees
Apr 23 - Apr 24
Outdoor Adventure Hub! Family Home in West Dover
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.
The price is ￥11,318
￥38,128 total
includes taxes & fees
Apr 23 - Apr 24
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
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 ￥33,840
￥41,386 total
includes taxes & fees
Apr 26 - Apr 27
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)
"Cozy as described. Minimal ammenities but all our needs were met. Shower was dark but a spare light lit it nicely. Watch your head, those over 6' tall, the overhang is cozy but bonkable."
United States
Andrew S.
The price is ￥22,238
￥44,045 total
includes taxes & fees
Apr 23 - Apr 24
Cozy cabin in charming Londonderry
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
The price is ￥7,811
￥35,526 total
includes taxes & fees
Apr 25 - Apr 26
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
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)
"Perfect spot to jump onto the mountain and ski. Two adults and 4 kids, and we had plenty of space for a long weekend."
United States
Allison T.
The price is ￥19,926
￥66,469 total
includes taxes & fees
Apr 23 - Apr 24
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
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)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is ￥17,934
￥47,988 total
includes taxes & fees
Apr 23 - Apr 24
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Smart TV, fireplace, stereo

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is ￥48,301
￥76,772 total
includes taxes & fees
Apr 23 - Apr 24
LUXE Forest Retreat
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.
The price is ￥14,449
￥52,181 total
includes taxes & fees
Apr 23 - Apr 24
Cozy Bromley Retreat
Property grounds

Lovely ski-in/out condo steps from ski lift with trails and amazing views

Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton
8.4 out of 10, Very Good, (33 reviews)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
United States
John N.
The price is ￥11,318
￥48,239 total
includes taxes & fees
Apr 23 - Apr 24
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Smart TV, fireplace, books

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

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (109 reviews)
"Great Condo. We had plenty of space. Wendi was very responsive and even accommodated us checking in an hour early when we arrived in town. We would definitely come back. "
United States
Barbara M.
The price is ￥21,520
￥45,406 total
includes taxes & fees
Apr 23 - Apr 24
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

8/10 Good
"Excellent breakfast good parking safe atmosphere helpful staff and very clean overall "
Danny 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG

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
  • Use the map to find apartments and other holiday homes in the Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

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 Magic Mountain Ski Resort and Jamaica State Park.

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.