Windham Holiday Rentals

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Our top choices for Windham holiday rentals

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, (37 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is HK$1,233
HK$2,266 total
includes taxes & fees
13 May - 14 May
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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.
The price is HK$1,331
HK$2,823 total
includes taxes & fees
14 May - 15 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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 HK$1,374
HK$2,486 total
includes taxes & fees
26 May - 27 May
Family Friendly Hilltop House In Putney Vermont

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 HK$2,153
HK$2,642 total
includes taxes & fees
26 May - 27 May
Owl's Nest Treehouse

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 HK$384
HK$1,745 total
includes taxes & fees
13 May - 14 May
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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 HK$1,752
HK$2,088 total
includes taxes & fees
13 May - 14 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

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 HK$1,253
HK$2,245 total
includes taxes & fees
28 May - 29 May
Wellness Getaway with a Personal Sauna, and Private River Beach!

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.
The price is HK$979
HK$3,264 total
includes taxes & fees
13 May - 14 May
Ski-In/Out Condo with Mountain Views, and Washer/Dryer

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.
The price is HK$881
HK$2,374 total
includes taxes & fees
13 May - 14 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

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 HK$939
HK$2,988 total
includes taxes & fees
13 May - 14 May
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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 HK$710
HK$2,536 total
includes taxes & fees
13 May - 14 May
Cozy Bromley Retreat

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)
"Unit was as advertised. Clean and comfortable."
United States
Ralph D.
The price is HK$587
HK$2,031 total
includes taxes & fees
16 May - 17 May
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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.
The price is HK$881
HK$2,374 total
includes taxes & fees
14 May - 15 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

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.
The price is HK$479
HK$2,453 total
includes taxes & fees
13 May - 14 May
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

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.
The price is HK$550
HK$2,973 total
includes taxes & fees
13 May - 14 May
Chalet Mount Snow/Stratton Skiing/hiking

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)
"Poor management company. Great lodge. "
United States
Billy W.
The price is HK$1,041
HK$3,024 total
includes taxes & fees
13 May - 14 May
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

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 HK$1,073
HK$2,139 total
includes taxes & fees
13 May - 14 May
The Studio with a View. Bring your dog, too!

LUXE Forest Retreat

LUXE Forest Retreat
Chester
The price is HK$2,372
HK$3,761 total
includes taxes & fees
13 May - 14 May
LUXE Forest Retreat

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 HK$1,198
HK$4,083 total
includes taxes & fees
13 May - 14 May
Outdoor Adventure Hub! Family Home in West Dover
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

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:

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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 holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windham has to offer?

Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna: This highly rated holiday home rental in Windham is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windham?

With 12 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Magic Mountain Ski Resort and Ball Mountain Dam.

What’s a holiday rental in Windham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windham. Holiday rentals feature extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a family trip.