Search Vacation 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month

Compare 634 Vacation Homes in Windham with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (8)
"Wonderful location close to Woodstock and hiking. Enjoyed the quiet solitude and this super cozy home with gleaming hardwood floors and comfy sofa. Very clean and neat. We Would stay again and there was an overnight snowfall that created a glistening storybook setting. So beautiful in winter and it was a fun birthday weekend! Cheers! Thank you to my hosts! "
The price is SAR 353
SAR 986 total
includes taxes & fees
2 Feb - 3 Feb
Quaint Cottage with Peloton Bike & Sauna near Skiing

Magical Home Located in Windham and Catskills

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great location and clean and owner was generous. "
Magical Home Located in Windham and Catskills

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 SAR 844
SAR 1,703 total
includes taxes & fees
2 Feb - 3 Feb
The Tipsy Gypsy

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

9.4 out of 10, Exceptional, (28)
"Wonderful coszy spot perfect location for singles and couples even family "
The price is SAR 356
SAR 544 total
includes taxes & fees
6 Feb - 7 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

10.0 out of 10, Exceptional, (148)
"We went with 3 families (kids 4-14) and had the best time !! Great house for a group. We were 18 total. Awesome location. The kids loved playing in the snow and visiting with the cows! The grounds were really beautiful. The house had plenty of room. The bunk rooms were awesome for kids. Upstairs master has a tiny room a one single bed off of it, perfect for a toddler or baby. Two living rooms for multiple sports game watching. Short drive to the mountain and restaurants. We even brought food...
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.

10.0 out of 10, Exceptional, (6)
"Beautiful log cabin with a great and easy to function fireplace. The host has a shed filled with firewood, starter wood and charcoal which was such a tremendous and pleasant surprise. The sunroom facing the mountains and a backyard that drops into the woods is a phenomenal place to have a morning cup of coffee or just chill in anytime. Huge master bedroom and 2 additional bedrooms offer plenty of space for a family of 4. Kitchen has all of the needed appliances/accessories. Great washer and...
A world where time stands still, close to Belleayre Ski & Wedding venues.

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

9.6 out of 10, Exceptional, (21)
"Had a great 2 night stay. Location is close to Hunter. "
The price is SAR 897
SAR 1,892 total
includes taxes & fees
18 Feb - 19 Feb
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!

Cozy Country Farmhouse Along the Catskill Scenic Trail

10.0 out of 10, Exceptional, (119)
"Great house, bucolic setting, nice proximity to ski slopes! Very gracious and helpful host and house caretakers. Would stay here again."
The price is SAR 656
SAR 1,191 total
includes taxes & fees
13 Feb - 14 Feb
Cozy Country Farmhouse Along the Catskill Scenic Trail

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

9.8 out of 10, Exceptional, (13)
"Perfect stay. Clean, warm and close to the mountain. "
The price is SAR 596
SAR 1,164 total
includes taxes & fees
12 Feb - 13 Feb
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Inviting, Cozy Catskills Home - Primed for Fall!

10.0 out of 10, Exceptional, (3)
"Very nice house conveniently located on Rt28. We enjoyed our stay there for a weekend. Unfortunately the fireplace did not work but the living room was cozy anyway. "
Inviting, Cozy Catskills Home - Primed for Fall!

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

10.0 out of 10, Exceptional, (213)
"Excellent communication. Cozy home. Really enjoyed our stay. "
The price is SAR 1,497
SAR 2,948 total
includes taxes & fees
5 Feb - 6 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

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

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!!

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

9.6 out of 10, Exceptional, (88)
"Very farm/ old fashion decoration which we loved. House is just great for Families that have teenagers. A lot of entertainment in the house and around the neighborhood. Close to Mountain and shops. Kinda upset with the heating but we didn’t mind wearing some extra clothing. Very good communication with the Landlord in every aspect. Will come back and stay again!! "
LOOKING FOR A HEAVENLY GETAWAY

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 SAR 1,493
SAR 2,877 total
includes taxes & fees
3 Feb - 4 Feb
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

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

2.0 star property
7.8 out of 10, Good, (6)
"We loved spending the weekend at Mommom"
The price is SAR 563
SAR 1,155 total
includes taxes & fees
2 Feb - 3 Feb
Cozy chic 2-bdroom bungalow with Sauna, Fireplace, Fast WiFi in quaint Phoenicia

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (127)
"Clean, "
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

Other property types in Windham

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

10.0 out of 10, Exceptional, (148)
"We went with 3 families (kids 4-14) and had the best time !! Great house for a group. We were 18 total. Awesome location. The kids loved playing in the snow and visiting with the cows! The grounds were really beautiful. The house had plenty of room. The bunk rooms were awesome for kids. Upstairs master has a tiny room a one single bed off of it, perfect for a toddler or baby. Two living rooms for multiple sports game watching. Short drive to the mountain and restaurants. We even brought food...
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

Tuscan Year Round Beauty - Pickleball Court

10.0 out of 10, Exceptional, (98)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court

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

9.0 out of 10, Wonderful, (38)
"I would totally recommend! It was a very practical apartment. I stayed with my spouse and my parents. The location was great, the manager was very arranging with the check-in time, and we really appreciated that we had two floors and two full bathrooms, one for my parents, and one for me and my spouse. Wish we had stayed longer to take advantage of the nice balcony"
The price is SAR 600
SAR 900 total
includes taxes & fees
11 Feb - 12 Feb
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
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.