Windham Holiday Rentals

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Check prices for these dates

Tonight
7 Jul - 8 Jul
Tomorrow
8 Jul - 9 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Windham

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Smart TV, fireplace, table football, ping pong

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (49)
"Consistently great time at this place (3rd time there)"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.
Long Trail House at Stratton Mountain Resort
Pool

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is HK$2,546
HK$3,165 total
includes taxes & fees
24 Jul - 25 Jul
Long Trail House at Stratton Mountain Resort
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (210)
"Location was perfect. Cabin cute and comfortable. Pond was an amazing bonus with lots of cool birds. We had the best vacation there ever!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Quaint lakefront home with a private deck, firepit, and dock
Property grounds

Quaint lakefront home with a private deck, firepit, and dock

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a private deck, firepit, and dock
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.0 out of 10, Very good, (38)
"Had a business retreat with 6 associates. The cabin was great and operated as one would expect for a ski cabin. Nice fire place and hot tub. The TVs are older so they have a hard time connecting to the WIFI for Netflix, Prime, etc. I recommend bringing agame console aor "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (221)
"Cabin was beautiful! Love the little stream outside. Very close to restaurants, shopping, and hiking trails. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
TV, fireplace, video games

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

10.0 out of 10, Exceptional, (20)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
3 bedrooms, Internet, bed sheets

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

9.0 out of 10, Wonderful, (25)
"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "
Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Miscellaneous

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

10.0 out of 10, Exceptional, (17)
"Loved this property. Was clean, well maintained, and cozy. My partner loved the size and the full kitchen. Was a good distance from Ludlow downtown, not too far. "
The price is HK$1,374
HK$2,444 total
includes taxes & fees
29 Jul - 30 Jul
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Fridge, microwave, oven, stovetop

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8.0 out of 10, Very good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (157)
"Thank you for a peaceful weekend away in a charming cottage!"
The price is HK$1,334
HK$2,875 total
includes taxes & fees
8 Jul - 9 Jul
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Solitude Village at Okemo
Private kitchen

Solitude Village at Okemo

4.0 star property
8.0 out of 10, Very good, (26)
"Beautiful Area. "
Solitude Village at Okemo
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
The Mountain Escape!
Fridge, microwave, oven, stovetop

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"It was a perfect house and great location! Would definitely stay again!"
The price is HK$870
HK$5,959 total
includes taxes & fees
8 Jul - 9 Jul
The Mountain Escape!
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Interior

Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

10.0 out of 10, Exceptional, (24)
"A terrific place. Highly recommended. We had a great family ski vacation."
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Interior

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (201)
"This location is awesome. Close to town and skiing but we felt like we were secluded in the forest when sitting in the hot tub. We had a great time!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (211)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
Indoor pool, a heated pool

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Property grounds

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

9.6 out of 10, Exceptional, (15)
"Happy experience and plenty of room. Everyone enjoyed the lake and sounding places."
8-bedroom vacation home just 16 minutes from Golf Club at Equinox
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

9.4 out of 10, Exceptional, (23)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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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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?

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.: 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 9 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 Vermont Country Store, 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.