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Compare 770 Vacation Homes in Windham with updated reviews, rates, and availability.

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, (19)
"Absolutely loved my stay at this tiny getaway house! The space was cozy, well-designed, and had everything I needed for a relaxing escape. The peaceful surroundings and thoughtful touches made it truly special. Perfect for unplugging and recharging. Can’t wait to come back for another retreat!" "
Dog-friendly chalet cabin with valley view, deck, and private hot tub
New Ludlow Village Home with Stunning Okemo Mountain View
Exterior

New Ludlow Village Home with Stunning Okemo Mountain View

The price is AED 2,196
AED 3,850 total
includes taxes & fees
2 Jan - 3 January 2025
New Ludlow Village Home with Stunning Okemo Mountain View
Primely Located Dover Escape < 1 Mi to Mt Snow!
Dover Vacation Rental | 2BR | 2BA | 1,350 Sq Ft | Stairs Required

Primely Located Dover Escape < 1 Mi to Mt Snow!

9.6 out of 10, Exceptional, (15)
"Location was perfect with the Moover transfer right on the door and even walking distance to the ski mountain(8’ walk). House was clean and had everything we needed. The only thing that could be better was the communication with the apt management/ owner. We couldn’t find the pool or hot tub and got no answer after asking. We had other questions that never got answered too. But overall for it was a great New year’s holiday!"
Primely Located Dover Escape < 1 Mi to Mt Snow!
Fabulous Mountain Top Retreat - 10 minutes from mount snow!
Private kitchen

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!
Cozy Cabin Between Stratton Resort & Mount Snow
Stratton Vacation Rental | 3BR | 1.5BA | 1,100 Sq Ft | Stairs Required

Cozy Cabin Between Stratton Resort & Mount Snow

Cozy Cabin Between Stratton Resort & Mount Snow
Charming 3-bedroom house in Ludlow with WiFi access
Exterior

Charming 3-bedroom house in Ludlow with WiFi access

Charming 3-bedroom house in Ludlow with WiFi access
The Green Mountain Chapel // Old Church repositioned into 3 BR
Exterior

The Green Mountain Chapel // Old Church repositioned into 3 BR

2.0 star property
10.0 out of 10, Exceptional, (11)
"I really loved this place and plan to return. Every thing about this chapel was gorgeous! The openness of the house was perfect and allows for being able to see the stunning stained glass from just about anywhere you are. The bathrooms were fantastic. This was the only place I've rented out that actually had the warm cozy home feel which we really loved. I also very much love that he had actual art around the chapel. I also greatly appreciate Tylers communication with the check-in process and...
The Green Mountain Chapel // Old Church repositioned into 3 BR
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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 "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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

8.2 out of 10, Very Good, (34)
"All in all it was a great trip. The place was very cute and as described. The upstairs bedrooms are not for light sleepers as the walls only go so far up so they are not really divided. I had read this in other reveiws but honestly for us it wasn't a problem. We went as a family group and it was kind of nice to be able to lay in bed and talk to the others in the room next to you. When we got there the hot tub was so hot that we were not able to get in. Maybe a problem with the thermostat but...
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
In the guest house yard.

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

9.4 out of 10, Exceptional, (19)
"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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!
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
Beautiful 4 Bedroom Townhome Minutes from Mt Snow
Living area

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

9.6 out of 10, Exceptional, (19)
"The property has a great location to so many activities, shops and places to eat. The house was a few steps from the pool which my kids loved"
Beautiful 4 Bedroom Townhome Minutes from Mt Snow
Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
Summer view of the home

Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE

9.8 out of 10, Exceptional, (91)
"Great weekend! Don't be deceived by your first impression when pulling in. This home is huge ! The setting is private and quiet. Two family rooms provide space for younger ones. Large dining room table is great for meals and games. Kitchen is well equipped. Usable outdoor space is small but a large patio is located next to the woods and has a large hot tub, table that seats 6 , firepit, and a gas grill. This is where we spent our evenings."
Private Home on Okemo with HOT TUB. WALK TO SKI TRAIL OR DRIVE 2 MIN TO LODGE
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (18)
"Everything about this house was great! We will definitely be back!"
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
Exterior

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (38)
"Great house for the family. Easy to jump on shuttle and hit the slopes. Easy to just drop your bags and enjoy the view of the mountain. Comfy couches. Big dining table to gather around. Kitchen has everything you need. Well stocked with linens and towels. Owner was communicative and helpful."
The price is AED 404
AED 1,233 total
includes taxes & fees
27 Jan - 28 January 2025
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
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
5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!
Exterior

5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!

10.0 out of 10, Exceptional, (1)
"House looks exactly as it does in the photos. No real yard, but the house itself is very comfortable. Plenty of space, comfortable beds and accommodating common areas. We struggled with the Internet through the duration of our stay, due to storms in the area. The property managers were in constant communication with us, but couldn't get the Internet service provider to resolve the issue. House is less than 10 minutes from Stratton Mountain, which is great. Unfortunately, it rained for the...
5BR, 6 min from Stratton, pet friendly, private, jacuzzi tub, wrap around deck!
Wardsboro Family Home: 7 Mi to Mount Snow!
Wardsboro Vacation Rental | 5BR | 2.5BA | 2,015 Sq Ft | Steps Required for Entry

Wardsboro Family Home: 7 Mi to Mount Snow!

10.0 out of 10, Exceptional, (3)
"Perfect vacation rental! Very clean, comfortable beds and perfect for 2 families. We went during ski season so the mudroom was tight but adequate. We would definitely stay there again!"
Wardsboro Family Home: 7 Mi to Mount Snow!
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)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,246
AED 1,548 total
includes taxes & fees
8 Jan - 9 January 2025
Long Trail House at Stratton Mountain Resort
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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 "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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.