Holiday Homes in Windham

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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

Featured Holiday Homes in Windham

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

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 with Peloton Bike & Sauna near Skiing
Property grounds

Quaint Cottage with Peloton Bike & Sauna near Skiing

9.8 out of 10, Exceptional, (11)
"We’ve had three weeks at this property and one more to go. It’s been simple and exactly what we needed.Communication with the property manager has been exceptional"
Quaint Cottage with Peloton Bike & Sauna near Skiing
Magical Home Located in Windham and Catskills
Property grounds

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
Private kitchen

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 AU$723
includes taxes & fees
23 Feb - 24 Feb
The Tipsy Gypsy
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Aerial view

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 AU$263
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
Property grounds

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.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (7)
"Spacious country cabin is an absolute gem! Beautifully decorated with a warm and inviting atmosphere, it strikes the perfect balance between rustic charm and modern comfort. Every detail, from the cozy fireplace to the thoughtfully curated decor, makes it feel like a home away from home.The location is fantastic—just a short drive to the ski slopes, making it an ideal spot for a winter retreat. After a day on the mountain, relaxing in the hot tub was the perfect way to unwind. Highly recommend...
A world where time stands still, close to Belleayre Ski & Wedding venues.
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
Smart TV, fireplace, computer monitors

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
Exterior

Cozy Country Farmhouse Along the Catskill Scenic Trail

10.0 out of 10, Exceptional, (120)
"This home was so well cared for and clean and I wish I could have stayed later. Very nice "
The price is AU$507
includes taxes & fees
24 Feb - 25 Feb
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)
"Perfect stay. Clean, warm and close to the mountain. "
The price is AU$489
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!
Terrace/patio

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
Pool

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
Outdoor spa tub

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 AU$1,247
includes taxes & fees
18 Feb - 19 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
Hair dryer, towels

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, (91)
"This large home comfortably accommodated 16 guests ages 21 to 87. Ample bedrooms and bathrooms for a group this large are hard to find but this home has plenty. The large and well stocked kitchen was a great gathering space after a day on the slopes with plenty of space for chefs and sous-chefs to work while the rest watched while enjoying apres-ski activities. The dining room was great for evening board games and led easily to the living room for evening movies. We look forward to returning."
Birch Creek Retreat ~ 8br, 8ba, New Hot Tub + Sauna
Modern Cabin CLOSE to skiing, w/mountain & pond views, Hot Tub, games and more!!
Aerial view

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
Exterior

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 AU$1,130
includes taxes & fees
2 Mar - 3 Mar
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Cozy chic 2-bdroom bungalow with Sauna, Fireplace, Fast WiFi in quaint Phoenicia
Fridge, microwave, oven, stovetop

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 AU$486
includes taxes & fees
23 Feb - 24 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.
Don't see what you're looking for?
See all available properties in Windham
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Windham

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

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 AU$402
includes taxes & fees
23 Feb - 24 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
Property grounds

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.
Fridge, microwave, oven, stovetop

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.