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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 635 Vacation Homes in Windham with updated reviews, rates, and availability.

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
view of the back decks and steps down to our private dock

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (128)
"Stayed at the house over Christmas with family. The house is well-appointed with excellent heat. Hosts were excellent at communicating with us when we had questions."
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing
Quaint Cottage w/ Peloton & Sauna near Hiking

Quaint Cottage w/ Peloton & Sauna near Hiking

9.6 out of 10, Exceptional, (12)
"Once you connect to the wifi you can use your phone. The landlord as well as property manager are helpful and actually respond. Property is very peaceful!"
Quaint Cottage w/ Peloton & Sauna near Hiking
Magical Home Located in Windham and Catskills
Exterior

Magical Home Located in Windham and Catskills

2.0 star property
10.0 out of 10, Exceptional, (9)
"Great location and clean and owner was generous. "
Magical Home Located in Windham and Catskills
The Tipsy Gypsy
Exterior

The Tipsy Gypsy

9.8 out of 10, Exceptional, (20)
"Great location. Very clean and cozy. Very nice people to work with. My kids loved it as well."
The price is AED 826
AED 1,671 total
includes taxes & fees
24 Feb - 25 Feb
The Tipsy Gypsy
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
View from the balcony

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

9.4 out of 10, Exceptional, (29)
"Very good "
The price is AED 422
AED 606 total
includes taxes & fees
25 Feb - 26 Feb
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
Dancing Horse Farm Lodge | Spring

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (151)
"We had an amazing stay - and Greg was absolutely phenomenal with communication - especially with providing information on plowing during a snow storm while we were there. The property was gorgeous and just a few minutes away from Wyndham Mountain. The property was very clean and huge for the great price. We were able to have a wellness retreat and the amenities were great! "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
A world where time stands still, close to Belleayre Ski & Wedding venues.
Living room

A world where time stands still, close to Belleayre Ski & Wedding venues.

10.0 out of 10, Exceptional, (8)
"Just as advertised. Clean, comfortable, and inviting cabin perfect for relaxing after a day of skiing. The roads leading to the cabin are rural, and the driveway is a bit steep, so keep that in mind if you’ll be driving during or after a snowfall in the area. "
The price is AED 731
AED 1,927 total
includes taxes & fees
24 Feb - 25 Feb
A world where time stands still, close to Belleayre Ski & Wedding venues.
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Living area

SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

9.6 out of 10, Exceptional, (23)
"Beautiful place. Right across from Hunter mountain. We enjoyed our stay."
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Cozy Country Farmhouse Along the Catskill Scenic Trail
The farmhouse in summer.

Cozy Country Farmhouse Along the Catskill Scenic Trail

10.0 out of 10, Exceptional, (121)
"This home was so well cared for and clean and I wish I could have stayed later. Very nice "
The price is AED 643
AED 1,151 total
includes taxes & fees
2 Mar - 3 Mar
Cozy Country Farmhouse Along the Catskill Scenic Trail
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit
Outdoor dining

Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

9.8 out of 10, Exceptional, (14)
"House was perfect for the three of us. Close to Belleayre and a couple other towns. Was very clean for our arrival."
The price is AED 584
AED 1,129 total
includes taxes & fees
24 Feb - 25 Feb
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit
Inviting, Cozy Catskills Home - Primed for Fall!
Living area

Inviting, Cozy Catskills Home - Primed for Fall!

10.0 out of 10, Exceptional, (4)
"Property was exactly as described. Property was clean and well stocked with sheets, towels etc. great communication with property owner. A "
Inviting, Cozy Catskills Home - Primed for Fall!
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
The Hudson Valley is calling!

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.4 out of 10, Exceptional, (13)
"We had a lovely stay for our family of 5 during the week before xmas. The home was well appointed, with all the normal needs we have to cook, etc... The house was very quiet despite 5 of us being there. Everyone had their own space. Very cozy. Loved that there were games to play, we had a great family round of monopoly!The property manager was so responsive. We felt very supported and attended to. Despite the cold weather the house stayed plenty warm as well!We highly recommend this home and...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim
Exterior

7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

10.0 out of 10, Exceptional, (214)
"Great house for large group. Clean and well appointed. All the luxury’s of home. Everyone in our group loved it and had an amazing time."
The price is AED 1,084
AED 2,476 total
includes taxes & fees
25 Feb - 26 Feb
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (14)
"Master bath needs a taller toilet for older people Master shower needs an upgrade.."
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Birch Creek Retreat ~ 8br, 8ba, New Hot Tub + Sauna
Exterior

Birch Creek Retreat ~ 8br, 8ba, New Hot Tub + Sauna

10.0 out of 10, Exceptional, (92)
"We enjoyed our stay and had plenty of room for our whole family. Close to Belleayre and 30 mins from Hunter. "
Birch Creek Retreat ~ 8br, 8ba, New Hot Tub + Sauna
Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!
Our backyard In winter; view of mountains and frozen pond!!!

Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!

9.8 out of 10, Exceptional, (73)
"We had a great time. Nice house. Quiet and comfortable. Thank you. "
Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!
LOOKING FOR A HEAVENLY GETAWAY
THE PERFECT WINTER DESTINATION

LOOKING FOR A HEAVENLY GETAWAY

9.6 out of 10, Exceptional, (90)
"Great place -- very comfy with a lot of different rooms and amenities. While my wife and I had the run of the whole place, it was way more room than we needed -- place is perfect for a families or couples travelling together. Hot tub, game room (it was so cold we spent a lot of time here!), dining room, living room with pellet stove, "theater room" off the hot tub with a projection white screen, back deck with gas grill. Guests really have a lot of control over the experience depending on what...
LOOKING FOR A HEAVENLY GETAWAY
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Exterior

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

10.0 out of 10, Exceptional, (262)
"The property was great for our family of 15. Everyone had enough space. The kids enjoyed the bunk room and the games. Our only issue was there was dog hair on a large rug in the kitchen which was dealt with very quickly once the host received my message but it was also in the master bedroom. We had someone in our party who is highly allergic to dogs and the house is not pet friendly in the listing. All in all, great weekend away with the whole family. "
The price is AED 1,241
AED 2,593 total
includes taxes & fees
25 Feb - 26 Feb
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Cozy chic 2-bdroom bungalow with Sauna, Fireplace, Fast WiFi in quaint Phoenicia
living room with smartTV and wood burning fireplace

Cozy chic 2-bdroom bungalow with Sauna, Fireplace, Fast WiFi in quaint Phoenicia

2.0 star property
8.0 out of 10, Very Good, (7)
"We loved spending the weekend at Mommom"
The price is AED 551
AED 1,150 total
includes taxes & fees
24 Feb - 25 Feb
Cozy chic 2-bdroom bungalow with Sauna, Fireplace, Fast WiFi in quaint Phoenicia
Beautiful new house 3/4 mile from Hunter Mountain
Exterior

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (128)
"Always a great stay at this beautiful house!"
Beautiful new house 3/4 mile from Hunter Mountain
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

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Balcony

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

9.2 out of 10, Wonderful, (39)
"Easy and convenient, would stay again. "
The price is AED 624
AED 926 total
includes taxes & fees
24 Feb - 25 Feb
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
Dancing Horse Farm Lodge | Spring

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

10.0 out of 10, Exceptional, (151)
"We had an amazing stay - and Greg was absolutely phenomenal with communication - especially with providing information on plowing during a snow storm while we were there. The property was gorgeous and just a few minutes away from Wyndham Mountain. The property was very clean and huge for the great price. We were able to have a wellness retreat and the amenities were great! "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
JUNE 2024 --Plenty of parking + electric charging

GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.

9.8 out of 10, Exceptional, (9)
"We had the best time! The property was perfect! Plenty of bedrooms and bathrooms plus gathering spaces galore ! The kitchen was stocked with all the necessities. We had 6 children age 8 and under so the outside property was perfect. Just enough snow for a snowman and some sledding! Plus an enormous deck and wrap around porch. There was a laundry and plenty of towels , pillows and cozy blankets! We will definitely be back! "
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
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.