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Compare 83 Chalets in Windham with updated reviews, rates, and availability.

Beautiful Manchester VT Mountain Retreat w/Hot Tub

10.0 out of 10, Exceptional, (28)
"Brought friends from overseas to show them the Northeast, this remote house in the mountains was the perfect spot. It was not to far from the small cute town but far enough that it was extremely relaxing. The hot tub and fire was perfect, and the kitchen was wonderful to cook in 10/10 Excellent Stay!"
Beautiful Manchester VT Mountain Retreat w/Hot Tub

Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

10.0 out of 10, Exceptional, (33)
"The home was well appointed with all the amenities and plenty of room for our three families (6 adults and 6 kids). The game room downstairs and open concept living room were awesome and would have been used more often had the weather not been so perfect. The property is truly the star of this place, picturesque mountain views and an amazing fire pit. We will definitely be renting again."
Delightful Vacation Home - Minutes to Okemo, Direct Access to VAST trails

On Shuttle, 12 min walk to village. Late Check out. Private Baths

9.8 out of 10, Exceptional, (7)
"Great location and comfortable"
On Shuttle, 12 min walk to village. Late Check out. Private Baths

Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

10.0 out of 10, Exceptional, (9)
"Just got back from three nights at this wonderful property with a group of 50-somethings to compete in a gravel bike race. This property was ideally located near our start line, very very clean, plenty of room for us, basically as advertised. Would definitely rent here again in the future given all of the above.."
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

10.0 out of 10, Exceptional, (48)
"My family and I had a great stay at the Skylight Lodge. It is very different from other rentals, being a former inn. There is plenty of space for a big group and the two master suites are great. The fireplace in the main room is like something out of game of thrones, and was the highlight of the trip for the adults. The kids spent most of the time playing games in the second living room on the first floor. The house is also very conveniently located near Manchester. We would definitely come...
Summer Adventures Await -- Book now for the Horse Show & Explore Manchester

Okemo Mountain Chalet W/ Hot Tub and Game Room

9.8 out of 10, Exceptional, (157)
"This chalet was the perfect retreat for our Vermont getaway! The house is beautifully designed, incredibly relaxing, and comes fully equipped with all the essentials for a comfortable stay. We especially enjoyed the cozy fireplace. We stayed in the king bedroom on the top floor, and the new mattress made for an exceptionally comfortable sleep. The chalet served as our home base for a 4-night stay, allowing us to explore different areas of Vermont with easy day trips. Ludlow itself offers plenty...
Okemo Mountain Chalet W/ Hot Tub and Game Room

Expansive 7-BR Chalet 5-min from Mt. Snow

10.0 out of 10, Exceptional, (3)
"House is great, we had a large group. 2 living rooms, one with tv one without was a nice separation. To give some details on the layout, the bunk bed rm and twin room are off the living room on the main level, all other bd rooms are on the second floor. From the parking area to the main front door there are 31 steps.... not sure that was stated anywhere but hopefully everyone reads this review. I will stay here again if my group size demands it, it's close to mt snow, pretty secluded overall...
Expansive 7-BR Chalet 5-min from Mt. Snow

4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton

9.2 out of 10, Wonderful, (19)
"As a yearly VRBO renter I am accustom to renting a few houses and this one had some disappointing takes and some great attributes. First the houses layout and location is great for a large get together and the views are amazing! But apon arriving you could first tell the slate entry way and door knob was in need of repair. From there we had a few other dissapointments, the dishes were dirty, scattered about the kitchen. Towels were damp and we later learned why, it was because the dryer simply...
4BR / 3BA Smart Home w/ Hot Tub, Mountain View Ski Chalet 3 minutes to Stratton

Mountain chalet

10.0 out of 10, Exceptional, (38)
"This is our third year staying at this mountain chalet and we will continue to return in the future! The cleanliness, comforts and location are nothing short of perfect! Thank you for making this beautiful home available for rental. Looking forward to next year!!"
Mountain chalet

Classic Alpine Vermont Chalet

10.0 out of 10, Exceptional, (9)
"We loved everything about this property. Lots of bedrooms, comfortable beds, big living room and kitchen area and very close to the downtown area. I highly recommend this house for large families looking for a place to stay in Vermont!"
Classic Alpine Vermont Chalet

WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.

9.8 out of 10, Exceptional, (31)
"Close to EVERYTHNIG!"
WE ARE BACK! COME AND ENJOY YOUR STAY AT OUR TREE HOUSE LIKE! CHECK LOW RATES.

Stylish Mountain Getaway close to Stratton w/ Spa

10.0 out of 10, Exceptional, (6)
"Amazing! Host was readily available to handle any questions and the house was very comfortable and relaxing. "
Stylish Mountain Getaway close to Stratton w/ Spa

New! Custom Chalet minutes from Mt Snow w/ Hottub

10.0 out of 10, Exceptional, (1)
"Our group of 7 couples have b"
New! Custom Chalet minutes from Mt Snow w/ Hottub

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

9.6 out of 10, Exceptional, (54)
"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

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

10.0 out of 10, Exceptional, (18)
"Stay was perfect"
Luxury 8BR Ski In/Out Okemo Chalet on Sachem Trail Sleeps 22 Adults

Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

9.6 out of 10, Exceptional, (45)
"We had a very nice stay. The house had plenty of room for our family including the living, dining, and sleeping areas. The location was great."
Walk to the village 6bed 4bath sleeps 15; newly renovated with 2 skylights.

Cozy Creekside Chalet centrally located near 4 ski resorts

10.0 out of 10, Exceptional, (7)
"We had the best time at this cozy spot with some friends for a weekend - highly recommend!"
The price is AED 882
AED 2,065 total
includes taxes & fees
25 Nov - 26 Nov
Cozy Creekside Chalet centrally located near 4 ski resorts

Green Mountain Manor - Ski and Summer Chalet

9.8 out of 10, Exceptional, (7)
"Relaxing VT stay . You are in a rural setting but places to stock up on supplies was less then 10 miniutes away . We watched the fireworks that stratton displayed pretty much from the comfort of the property .Our children are young adults and they had a blast finding local swimholes . As well as spending a day at Bromley Mountain ( 20 mins away ) where they did water slides , alpine slides , the giant swing to name a few . House is large and the ability to accomodate large families or groups ....
Green Mountain Manor - Ski and Summer Chalet

New-Crown Jewel at Mount Snow-Ski-on/off

New-Crown Jewel at Mount Snow-Ski-on/off

Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck

9.4 out of 10, Exceptional, (6)
"We were absolutely thrilled to experience a fresh powder drop during our stay, which was a delightful surprise in an otherwise dry season. The house surpassed all our expectations, providing the perfect haven for our large group. It was impeccably clean, incredibly warm, and featured an abundance of comfortable beds, all while being conveniently close to the mountain. A standout feature for us was the Tesla charger in the garage, which met our specific needs perfectly. We are already eagerly...
The price is AED 1,488
AED 3,549 total
includes taxes & fees
24 Nov - 25 Nov
Sunny Stratton Mountain Retreat: 5BD Modern Oasis w/Hot Tub, Pond, & BBQ Deck
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.

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!!

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

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.