Search Vacation Homes in Windham

Compare 640 Vacation Homes in Windham with updated reviews, rates, and availability.

HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (34)
"This house was adorably charming and perfect for a weekend getaway in Woodstock. We loved watching wildlife from the beautiful kitchen windows and the privacy the property provided. Our pup loved the front sun room and keeping an eye on the yard. Thank you for sharing your home!"
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
9.8 out of 10, Exceptional, (7)
"Our stay was really nice. The house was clean and had everything we needed. We loved being able to walk into town. "
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
The Catskills Red Barn
10.0 out of 10, Exceptional, (36)
"Really cute weekend stay for my partner, pup and I. Easy access to the main road which was very convenient and great yard for the dog! Bathroom needs a little updating :) "
The Catskills Red Barn
Bright, historic Woodstock home close to town
9.8 out of 10, Exceptional, (6)
"We loved the historic nature of the property. It is in a beautiful setting, just a short walk from downtown Woodstock. Cheryl was very responsive and helpful. Wish we had more time to enjoy the outdoor space!"
Bright, historic Woodstock home close to town
Studio 3 BEDS-SLEEPS 3
9.4 out of 10, Exceptional, (27)
"Very accommodating. Easiely accessible. Loved the balcony!"
The price is AED 294
AED 477 total
includes taxes & fees
24 Nov - 25 Nov
Studio 3 BEDS-SLEEPS 3
TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6
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 AED 441
AED 713 total
includes taxes & fees
25 Nov - 26 Nov
TOWNHOUSE-LOFT-30 ft balcony Mt View/6 BEDS/ Sleeps 6
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
10.0 out of 10, Exceptional, (212)
"We had a fantastic stay in Valentyna's home. We had a large group of 16 at the home during labor day weekend. We found the house large, clean, updated and had plenty of space. The bedrooms are roomy, the living spaces are even larger than pictured, and the five different outdoor areas are fantastic. The house has every amenity you can ask for. Direct lake access is steps from the house and the house is close to Hunter for the winter months. We had a great time and would happily stay again. "
The price is AED 1,319
AED 2,722 total
includes taxes & fees
24 Nov - 25 Nov
7Bdr/5Bth, Amazing View, Lake,1/2 ml Hunter Mountain, Hot Tub/Sauna. Ski, Swim
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
10.0 out of 10, Exceptional, (90)
"The house and its amenities were perfect for our group, and the host was easy to communicate. "
The price is AED 1,414
AED 2,516 total
includes taxes & fees
24 Nov - 25 Nov
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE
A'Neils Windham Ski Lodge & Family Retreat
10.0 out of 10, Exceptional, (26)
"Beautiful historic house in Windham NY, great for large gatherings. Plenty of bedrooms with multiple beds and private baths. Spacious common area to relax at the end of the day. Large dining room that will accommodate all your guests and a large well stocked kitchen with everything you need to cook and serve. Relax on the covered front porch and enjoy nature or challenge your guests in a game of pool. The house was very clean on arrival with easy check in access. All in all it’s a great place...
A'Neils Windham Ski Lodge & Family Retreat
Catskill Mountain Retreat -- private, beautiful views
9.8 out of 10, Exceptional, (98)
"Location was great. Very peaceful "
Catskill Mountain Retreat -- private, beautiful views
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
10.0 out of 10, Exceptional, (177)
"David was very communicative and has a great home. Location felt surrounded by nature but was a very short drive into town. "
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
Guest House Catskill Mountains Private Backyard Fire Pit BBQ Grill Ski Golf Hike
9.8 out of 10, Exceptional, (175)
"My friend and I came to New York to visit the different Watchtower facilities. But added a few days to enjoy the country around the Catskills and the changing of the leaves. Liz was very helpful with recommendations and we entered the house welcomed by a warm fire insert. So homey. Really enjoyed our stay. "
Guest House Catskill Mountains Private Backyard Fire Pit BBQ Grill Ski Golf Hike
Dingley Dell Villa Windham with Movie Room, Hot tub, 6 Bedrooms, 4 bathrooms
10.0 out of 10, Exceptional, (3)
"Such a beautiful and convenient location for all of us who were attending a wedding at the Windham Manor! The outside deck and fire pit were a wonderful place to relax and just be together! Thanks for a great stay in the Catskills! "
Dingley Dell Villa Windham with Movie Room, Hot tub, 6 Bedrooms, 4 bathrooms
Charming 3-bedroom house in marvelous Hunter. Hot Tub, Pool Table, Ski, Lakes
10.0 out of 10, Exceptional, (4)
"We stayed here in late fall to enjoy some nature, railway adventures and home cooking and Isabel’s rental was absolutely perfect for our group! We enjoyed the hot tub, cozy living room, walking about the yard and the pool table/bar lounge in the basement as well. The whole home is decorated so nicely and kitchen was stocked with everything we needed to cook eat and drink all that we brought. Bonus points for adorable and comfortable bedrooms (especially pillows) and friendly neighbors! We look...
The price is AED 1,192
AED 2,202 total
includes taxes & fees
23 Nov - 24 Nov
Charming 3-bedroom house in marvelous Hunter. Hot Tub, Pool Table, Ski, Lakes
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (143)
"A Big House has enough rooms and beds. Had mostly everything needed, and owner able to answer questions and solve problem in time. the backyard and forest would be better view in spring or summber. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
9.8 out of 10, Exceptional, (19)
"Really love the mountains and fall leaves and lots to do and see in the area, unlike some resort towns. The accommodations were very nice, thank you! "
SPECTACULAR CATSKILL OASIS with Hunter Mountain Views, INCREDIBLE LOCATION!!!
FOUR SEASON Catskills Home - Secluded & Spacious w/ Secret Waterfall
10.0 out of 10, Exceptional, (35)
"We had an incredible weekend away at this gorgeous home. So many amazing features, all neatly marked with clear instructions on how to use the various amenities in the house. We were very impressed/ Our group of 9 friends enjoyed it immensely. I've already recommended this to others! Would come back again!"
FOUR SEASON Catskills Home - Secluded & Spacious w/ Secret Waterfall
CREEK MOUNTAIN VIEWS IN CATSKILL RETREAT.. with weekly discounts.
9.8 out of 10, Exceptional, (36)
"The property was absolutely beautiful and the location was great not too far from the town and yet the property felt secluded and private. Great communication with the host and there was a very helpful instruction and information book as well as instructions for just about everything in the house. I am looking forward to my next stay at the property "
CREEK MOUNTAIN VIEWS IN CATSKILL RETREAT.. with weekly discounts.
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
10.0 out of 10, Exceptional, (119)
"Girls weekend! Three 49 year old college roommates meeting up for a quick weekend of laughs. Best time. The house is adorable, comfortable, cozy rustic charm but also totally modern. Enjoyed Tinker Street, dinners out and a short hike. Highly recommend."
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
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

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (143)
"A Big House has enough rooms and beds. Had mostly everything needed, and owner able to answer questions and solve problem in time. the backyard and forest would be better view in spring or summber. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
Tuscan Year Round Beauty - Pickleball Court
10.0 out of 10, Exceptional, (97)
"Awesome"
Tuscan Year Round Beauty - Pickleball Court
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
9.8 out of 10, Exceptional, (7)
"Our stay was really nice. The house was clean and had everything we needed. We loved being able to walk into town. "
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.