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

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, (87)
"The house provided a darling stay in a cute little neighborhood. The house was very clean in the beds were comfortable to sleep in, which is very important to us. Thank you for a quick overnight stay and we will be back!"
The price is SAR 627
SAR 1,389 total
includes taxes & fees
20 Nov - 21 Nov
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lake
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (199)
"We had a wonderful 4 days/nights at Cozy Cottage. Perfectly named, well appointed decor and comfortable beds. Perfect for families. The fire pit, kayaks and conoe along with the string lights and sitting areas to watch the wood ducks and beaver family was the perfect way to decompress from the rat race."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Plenty of Room For Everyone! - 5 Minutes to Stratton
Fire Pit - Front Yard
Plenty of Room For Everyone! - 5 Minutes to Stratton
9.8 out of 10, Exceptional, (11)
"You have a lively property. My wife and I look for peace and quiet when we go away and your property fits the bill"
The price is SAR 899
SAR 3,325 total
includes taxes & fees
25 Nov - 26 Nov
Plenty of Room For Everyone! - 5 Minutes to Stratton
Okemo Mountain Lodging
Exterior
Okemo Mountain Lodging
3.5 star property
7.6 out of 10, Good, (26)
"I had an amazing time with my family, I will definitely be coming back "
Okemo Mountain Lodging
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
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.6 out of 10, Good, (17)
"The cabin was the perfect weekend getaway. We had issues with connecting the projector to the internet and finally gave up on trying to connect but other then that the overall experience was great. Will be staying here again in the future. "
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
9.8 out of 10, Exceptional, (67)
"This home is exactly as described online and the photographs are a true refection of the quality. Great space, layout, level of comfort, and extremely well equipped. The amenities offered within the association/village (swimming pool, tennis court, fitness room, games room...) were a bonus. We would definitely stay in this home again."
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Plenty of private open space to explore with the whole family!
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
10.0 out of 10, Exceptional, (49)
"We loved this property with stunning foliage, hiking trails, and perfect views. The house had everything we needed to accommodate a large group and more with lots of thoughtful touches. Plenty of space, panoramic views, screened in porch, fireplace, pool table, and connected speakers throughout. We have stayed at many different rentals for our annual trip over the years and this one is our new favorite."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
Living area
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
10.0 out of 10, Exceptional, (12)
"This house was great! It was very clean, had lots of bedrooms, and plenty of room for our group of 7 to have a great weekend. The host was super nice and responded quickly to messages. I would note that there are a lot of stairs, both to get into the house and within the house. Probably not a big deal for people who stay for skiing, but good to know if you have older guests or people who have trouble with stairs."
Cozy ski retreat on the Stratton Access Road - 5 minutes to the slope!
Hilltop 9-BR Mountain Retreat 5-min to Okemo
Pool
Hilltop 9-BR Mountain Retreat 5-min to Okemo
Hilltop 9-BR Mountain Retreat 5-min to Okemo
Sunny Stratton Townhome ~ 1 Mi to Skiing!
Stratton Vacation Rental | 3BR | 2.5BA | 1,600 Sq Ft | Stairs Required
Sunny Stratton Townhome ~ 1 Mi to Skiing!
10.0 out of 10, Exceptional, (4)
"Wonderful and clean townhome! Perfect location to be close to Stratton Resort. Thank you!"
Sunny Stratton Townhome ~ 1 Mi to Skiing!
New Chalet mins to Mt with Hot tub
Newly constructed cottage minutes from the mountain
New Chalet mins to Mt with Hot tub
10.0 out of 10, Exceptional, (2)
"Excellent house, very beautiful, very spacious and much better than what is seen in the photos 10 out of 10 I loved it, without a doubt I would return to this place with my family"
New Chalet mins to Mt with Hot tub
Walk to Ski Lift: Spacious Condo in West Dover!
West Dover Vacation Rental | 3BR | 3.5BA | Steps to Enter | 1,750 Sq Ft
Walk to Ski Lift: Spacious Condo in West Dover!
2.0 star property
Walk to Ski Lift: Spacious Condo in West Dover!
West Dover Townhome Near Mount Snow Shuttle Stop!
West Dover Vacation Rental | 4BR | 3.5BA | 1,800 Sq Ft | Stairs to Access
West Dover Townhome Near Mount Snow Shuttle Stop!
2.0 star property
West Dover Townhome Near Mount Snow Shuttle Stop!
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree!
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!
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!
Idyllic Lakefront House Suited Two Families
View from deck
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (153)
"Our stay was wonderful, and the hosts were more than accomadating! Lovely home and very convenient to Ludlow and Okemo. "
Idyllic Lakefront House Suited Two Families
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Your Barn!
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (196)
"Beautiful time of the year to enjoy this property and the surrounding woods and trails, plus Manchester. Our dogs love it here. "
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
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
7.8 out of 10, Good, (41)
"Can't beat the location. We had a great stay."
The price is SAR 278
SAR 1,013 total
includes taxes & fees
18 Nov - 19 Nov
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Interior
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, (30)
"One of the best experiences I’ve had. Communication before we arrived was as expected, and everything was better than the pictures reviews and descriptions."
The price is SAR 2,061
SAR 4,972 total
includes taxes & fees
24 Nov - 25 Nov
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
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.
Long Trail House at Stratton Mountain Resort
Living room
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is SAR 1,230
SAR 1,523 total
includes taxes & fees
18 Nov - 19 Nov
Long Trail House at Stratton Mountain Resort
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree!
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!
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!
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.