Search Vacation Homes in Windham

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windham vacation homes

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

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (59 reviews)
"Lovely hosts "
United States
Tyler G.
The price is AED 441
AED 762 total
includes taxes & fees
18 May - 19 May
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is AED 678
AED 1,890 total
includes taxes & fees
17 May - 18 May
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"Staying at this property was an absolute delight. The space was spotless, beautifully decorated, and felt even better in person than in the photos. Every detail - from the comfortable bedding to the amenities - made my stay feel effortless and relaxing. Check in was smooth. Overall an outstanding experience. Highly recommend this property! "
United States
Dikaury G.
The price is AED 612
AED 1,819 total
includes taxes & fees
26 May - 27 May
Pines Vignette • Modern 3BR Home in Windham

2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is AED 735
AED 1,991 total
includes taxes & fees
19 May - 20 May
2 Min Walk to Windham Town | Hot Tub | Fire Pit

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (4 reviews)
"We had a great three day getaway in Windham. The house was a great spot for a ski getaway in the mountains. Nice open floor plan and every bedroom had a bathroom which was great"
United States
Jim V.
Ask about Spring Specials!

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (2 reviews)
"I really enjoyed my time here. The house was comfortable, modern and well taken care of, and the property it was on was beautiful. Good access to town as well, and the full kitchen was well appointed. I had a really relaxing weekend, I'd book this again."
United States
Robert G.
The price is AED 2,351
AED 3,163 total
includes taxes & fees
18 May - 19 May
Ask about Spring Specials!

Ask about Spring Specials!

Ask about Spring Specials!
Windham
10.0 out of 10, Exceptional, (1 review)
"We had an amazing time in this magnificent, beautiful home. Our family books ski trips throughout the northeast twice a year as a group of 10 for the past 10 years. This house has by far ranked #1 as the best house we have stayed in. 10 minutes away from the mountain (Windham). 4 large sized bedrooms each with their own large bathrooms. A beautiful dream kitchen with all the essentials. We did plenty of cooking. We loved the open layout of the home. We will definitely be back for sure. "
United States
Anonymous traveler
Ask about Spring Specials!

Red Feather Lodge

Red Feather Lodge
3.0 star property
Windham
The price is AED 7,343
AED 7,930 total
includes taxes & fees
16 May - 17 May
Red Feather Lodge

Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access
Saugerties
9.8 out of 10, Exceptional, (16 reviews)
"The home was extremely clean and nicely appointed. Beds were very comfortable and kitchen was nicely equipped."
United States
Nancy B.
The price is AED 288
AED 978 total
includes taxes & fees
18 May - 19 May
Peaceful Cabin w/ Fire Pit & Creek Access

Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (11 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is AED 588
AED 1,254 total
includes taxes & fees
18 May - 19 May
Modern Luxurious Cabin, Catskills - The Tiny Nook

Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.4 out of 10, Exceptional, (15 reviews)
"Everything was perfect!"
United States
Jen C.
The price is AED 425
AED 1,197 total
includes taxes & fees
18 May - 19 May
Cozy Waterfall Oasis + Firepit

Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (10 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
The price is AED 661
AED 1,353 total
includes taxes & fees
17 May - 18 May
Brand New 2 Bdr. Townhome Minutes from Windham Mtn

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Phoenicia
9.2 out of 10, Wonderful, (38 reviews)
"Excellent location close to everything we needed. The property was clean and comfortable, and the WiFi was strong and dependable throughout our stay."
United States
Jessica P.
The price is AED 591
AED 1,361 total
includes taxes & fees
15 Jun - 16 Jun
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

The Bend: Stony Clove Suite • Pool • Sauna • Creek

The Bend: Stony Clove Suite • Pool • Sauna • Creek
Phoenicia
The price is AED 780
AED 1,335 total
includes taxes & fees
19 May - 20 May
The Bend: Stony Clove Suite • Pool • Sauna • Creek

Lakefront Luxe Retreat | Beach, Pools, Pickleball

Lakefront Luxe Retreat | Beach, Pools, Pickleball
Athens
10.0 out of 10, Exceptional, (1 review)
"The house was wonderful. It was clean, well-appointed, and the kitchen was fully stocked. The neighborhood was great, too."
United States
Kevin M.
The price is AED 878
AED 2,285 total
includes taxes & fees
18 May - 19 May
Lakefront Luxe Retreat | Beach, Pools, Pickleball

Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (12 reviews)
"Very clean and convenient location. Would stay again. Host was very communicative. "
United States
Shawn K.
The price is AED 841
AED 1,586 total
includes taxes & fees
17 May - 18 May
Midnight Fox

West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is AED 643
AED 1,678 total
includes taxes & fees
16 May - 17 May
West Kill Barnhouse: Ski, Work & Unwind

Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace

Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace
Tannersville
The price is AED 863
AED 2,261 total
includes taxes & fees
17 May - 18 May
Charming 3-bedroom house in Tannersville with AC, Firepit, Hottub, Fireplace

The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits

The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits
Phoenicia
The price is AED 893
AED 1,593 total
includes taxes & fees
19 May - 20 May
The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Tannersville
10.0 out of 10, Exceptional, (3 reviews)
"Excellent place, we loved the house and it had everything we needed to avoid getting out of the house since we had to go after a snowstorm. A very homey house and the hosts were very attentive and responded very quickly to our inquiries."
United States
Monica O.
The price is AED 845
AED 2,400 total
includes taxes & fees
27 May - 28 May
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windham Hotel Reviews