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
In two months

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

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

9.2 out of 10, Wonderful, (40)
"Really lovely place right in the heart of town. Owner and manager were great."
The price is AED 404
AED 661 total
includes taxes & fees
1 Apr - 2 Apr
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (39)
"The property was well maintained and a great space. The views along side the creek were amazing. "
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (172)
"This was an incredible place to stay for a snowy weekend with the family. The house is huge and and just beautiful. The hosts even had the long driveway plowed and stairs/walkway shoveled for us, would definitely recommend staying here. "
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

10.0 out of 10, Exceptional, (91)
"This Woodstock gem is a lovely and spacious getaway spot. We had plenty of room for two couples and our dogs to stay comfortably for multiple days. The house is very close to downtown Woodstock and has all of the amenities you could need. We particularly enjoyed the ping-pong table, fireplace, and hot tub. Additionally the host is responsive and cares about you having a comfortable stay. We would definitely stay here again!"
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

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

9.2 out of 10, Wonderful, (9)
"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 1,931 total
includes taxes & fees
17 Mar - 18 Mar
A world where time stands still, close to Belleayre Ski & Wedding venues.

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

9.8 out of 10, Exceptional, (16)
"After a day of skiing at Bellayre Mtn this very clean, comfortable cabins’ great location was the perfect place to unwind for the night."
The price is AED 584
AED 1,133 total
includes taxes & fees
12 Mar - 13 Mar
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

10.0 out of 10, Exceptional, (102)
"Thanks for a great place to hang for a ski weekend!"
The price is AED 1,010
AED 2,049 total
includes taxes & fees
1 Apr - 2 Apr
THE LAKEFRONT RETREAT - SKI, RIDE, GOLF, BIKE, HIKE

Tuscan Year Round Beauty - Pickleball Court

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

Victorian Catskill House w/ Game Room, Fire Pit, and Strong Wi-Fi

9.4 out of 10, Exceptional, (92)
"This house offered plenty of space and a great place to unwind after a day on the slopes. We enjoyed the closeness to the slopes (less than 15 minute drive) and cooked some great meals in the kitchen, dining on the glorious table in the dining room. My 9.5 month old grandson loved crawling through the “tunnel” under the long table;/)"
Victorian Catskill House w/ Game Room, Fire Pit, and Strong Wi-Fi

Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

10.0 out of 10, Exceptional, (122)
"Perfect location, cozy house keeps us coming back year after year! "
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

10.0 out of 10, Exceptional, (180)
"We had such a wonderful stay! "
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

9.8 out of 10, Exceptional, (70)
"Located close to Belleayre, easy check in and clean tidy place. Would use again for a visit."
Gorgeous Ski Chalet - 7 miles from Belleayre with hot tub

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

10.0 out of 10, Exceptional, (215)
"The house has hot tub, sauna and game room. It is perfect for both youths and adults."
The price is AED 1,083
AED 2,475 total
includes taxes & fees
12 Mar - 13 Mar
7Bdr/5Bth, Amazing View, Lake,1/2 ml Ski Hunter Mountain, Hot Tub/Sauna. Swim

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat

Phoenicia Retreat: Massive Private Entertaining Home with Fireplace & Pond

9.0 out of 10, Wonderful, (16)
"5 adults, 2 kids, one dog. Had plenty of room. Beautiful weather and enjoyed the outdoor decks. Overall very comfortable for us."
Phoenicia Retreat: Massive Private Entertaining Home with Fireplace & Pond

Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

9.6 out of 10, Exceptional, (178)
"We had an amazing time at this beautiful home! The house was spotless when we arrived, and we were welcomed with a warm fire already going in the wood stove – such a nice touch. Peter and Lara were there to greet us and give us a tour, making us all feel right at home. We also really appreciated how responsive they were when we had a small issue with the hot tub – they took care of it right away. The place is absolutely gorgeous and so unique – you can really see the love and care they put into...
Sauna, Hot-tub, Private Pool, fire-pit, pet friendly, Mountain views!

Catskill Mountain Retreat -- private, beautiful views

9.8 out of 10, Exceptional, (103)
"Close to ski areas. Great location "
Catskill Mountain Retreat -- private, beautiful views

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

Catskills Quaint Cottage w/ Peloton & Sauna near Hiking - Hunter and Belleayre

9.6 out of 10, Exceptional, (14)
"I stayed in this property for a total of 4 weeks. It was close to our work location, easily accessed, comfortable and clean. The shining star was the frequent and clear communication with the property manager CinthyaIf we find ourselves working in the area again, we'd look to book here as our first choice!"
Catskills Quaint Cottage w/ Peloton & Sauna near Hiking - Hunter and Belleayre

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.
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, (154)
"Large home with everything you’ll need. Plenty of towels, kitchen supplies, fridge space for a large party. Bedding was nice, with plenty of extra blankets. Greg was very easy to work with and answered all of our questions quickly. We would definitely book this property again. "
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat

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

9.2 out of 10, Wonderful, (40)
"Really lovely place right in the heart of town. Owner and manager were great."
The price is AED 404
AED 661 total
includes taxes & fees
1 Apr - 2 Apr
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.