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Compare 760 Vacation Homes in Windham with updated reviews, rates, and availability.

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!
Sit by the fire and then take a dip in the pool!

Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!

9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Ski & Ride VT! Private indoor pool to enjoy after a day on the slopes!
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi

10.0 out of 10, Exceptional, (43)
"Brad was a wonderful host and the home and area had so much for us to do. It was the perfect place to get away and be with friends. "
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

9.0 out of 10, Wonderful, (41)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool
Updated kitchen

Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool

10.0 out of 10, Exceptional, (9)
"We had a wonderful stay. We enjoyed the home and community amenities. Location was great and our family enjoyed the convenience of having the access to ski on / ski off. We look forward to our stay next year!"
Modern Ski In / Ski Out 4BR / 3BA Smart Home w/ Private Hot Tub and shared pool
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Take in stunning views from our large windows while cozied by the fire

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

10.0 out of 10, Exceptional, (21)
"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Property grounds

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

10.0 out of 10, Exceptional, (32)
"We had the most enjoyable and comfortable stay at this lovely home away from home! Jen was more than welcoming and always very responsive. The house was very clean and located conveniently across the street from the mountains. Looking forward to staying here again next season! :)"
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.
View of back of home and gardens from field

Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.

10.0 out of 10, Exceptional, (64)
"We had several events during our son's wedding weekend. The house and barn made for a great landing spot between events. We had plenty of room for all of our family. The property was very large and allowed for several sitting areas, both inside and outside. The landscape around the house made a great backdrop for pictures for the groom and groomsmen. The house has everything you need. "
Mountain views. Ski Bromley, Stratton. Minutes to restaurants, Equinox, Ekwanok.
Beaver Glen | House in Winhall with large deck - near Stratton & Bromley

Beaver Glen | House in Winhall with large deck - near Stratton & Bromley

9.0 out of 10, Wonderful, (4)
"Very Clean, roomy, nicely laid out, close to ski areas. Owner was responsive and available. All went very well. I would recommended this without reservation."
Beaver Glen | House in Winhall with large deck - near Stratton & Bromley
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski
Summit View from upper deck

Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

10.0 out of 10, Exceptional, (17)
"We had an amazing stay at this spacious townhome, just across from Mount Snow. The location was perfect for hiking, with stunning trails to explore throughout the area. We spent our days hiking and taking in the beautiful mountain views. The townhome is beautifully decorated and very comfortable. The living area with a cozy wood-burning fireplace was perfect for relaxing after a day outdoors. The fully equipped kitchen made it easy to cook and enjoy meals together, and we loved spending time on...
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
Main St., Manchester, Vt.

Miner Cottage-Historic Antique Home just steps from the Equinox Resort

10.0 out of 10, Exceptional, (22)
"GREAT TIME ! GREAT HOUSE"
Miner Cottage-Historic Antique Home just steps from the Equinox Resort
Family oriented community in country setting...10 minute walk to town center.
Front entry and...new to the market!

Family oriented community in country setting...10 minute walk to town center.

10.0 out of 10, Exceptional, (19)
"The property was really perfect. In perfect condition. Spotlessly clean. Nice views of the mountains. Great location for access to amenities."
Family oriented community in country setting...10 minute walk to town center.
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

10.0 out of 10, Exceptional, (3)
"The property is secluded but close enough to shops and restaurants. The deck is amazing with a jacuzzi and lounge chairs overlooking the golf course and mountains! Would definitely stay at again!"
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Located in the Okemo Mt. Community, a mile to the base lodge

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Back of Barn

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (54)
"We rented the barn as an overflow space from the main house. The barn has everything you need and is a really cool spot to sit and view the entire property."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome
Winter_holiday_ext_closeup_Battenkill_Valley_Mansion

HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome

10.0 out of 10, Exceptional, (55)
"The house is beautiful & has tons of nooks and crannies. Fun for exploring!"
HUGE Private VT Mansion: 15 bedrooms, 12 bath, Sleep 34! Ski Bromley & Stratton, yoga retreats, corporate offsites, DIY weddings, family reunions, Dogs welcome
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Living area

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (88)
"Very comfortable home. Loved the nostalgic feeling "
The price is AED 635
AED 1,388 total
includes taxes & fees
3 Dec - 4 Dec
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning
Renovated living, dining, and kitchen area complete with wood burning fireplace

Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning

10.0 out of 10, Exceptional, (21)
"Great property, there was everything that we needed for our weekend getaway."
Slopeside townhome on Okemo Ski Mountain! Summer Pool, Tennis & Air Conditioning
Magnificent Vermont home w/free WiFi, full kitchen, firepit, patio, & deck

Magnificent Vermont home w/free WiFi, full kitchen, firepit, patio, & deck

9.8 out of 10, Exceptional, (33)
"Lots of space to spread out. Kitchen was well appointed. Location was less than 10 minutes to Manchester. "
Magnificent Vermont home w/free WiFi, full kitchen, firepit, patio, & deck
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table
Open concept for larger groups

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

9.8 out of 10, Exceptional, (99)
"Nice, private and relaxing cabin in a great location on the mountain. Would definitely recommend and rent again "
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table
Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34
Exterior

Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34

9.8 out of 10, Exceptional, (75)
"We have a group which tries to get away to Vermont once a year. This was actually our second stay at the Base Lodge (first was in 2022). The property has plentiful accommodation and a great interior space just a short walk from central Ludlow. We also appreciate the quiet back yard amenities at the Lodge. The owners were very responsive during our stay, answering questions promptly and keeping track of our needs. We would definitely stay again. "
Base Lodge - shuttle rte in winter - 10 BR, 5 Bath, Slp 34
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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Other property types in Windham

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Exterior

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

10.0 out of 10, Exceptional, (39)
"This property was beautiful, clean, well maintained, had everything we needed. Wish we could have stayed longer! Thank you for a weekend we’ll never forget! We hope to rent this house again in the future. "
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Located in the Okemo Mt. Community, a mile to the base lodge

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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.