Windham Vacation Rentals

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Browse Select Windham Vacation Homes

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

9.2 out of 10, Wonderful, (35)
"Great place for an incredible price. We would definitely stay here again."
The price is CA $100
CA $182 total
includes taxes & fees
Aug 24 - Aug 25
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Tannersville Village on SawMill Creek Room #8- 2 Queen Bd

The price is CA $134
CA $310 total
includes taxes & fees
Aug 24 - Aug 25
Tannersville Village on SawMill Creek Room #8- 2 Queen Bd

Book Village Inn -Dickinson Room

8.0 out of 10, Very good, (1)
"This is a very nice Inn that needs some TLC. Room was clean with nice touches of coffee maker microwave and refrigerator. One downfall is no onsite parking have to park and walk. Owner was engaged"
The price is CA $140
CA $238 total
includes taxes & fees
Aug 27 - Aug 28
Book Village Inn -Dickinson Room

Book Village Inn - Twain Room

8.0 out of 10, Very good, (1)
"Quiet, near my travel objective, no interferences. "
The price is CA $126
CA $222 total
includes taxes & fees
Aug 27 - Aug 28
Book Village Inn - Twain Room

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

9.0 out of 10, Wonderful, (48)
"Great for in town stays"
The price is CA $162
CA $285 total
includes taxes & fees
Aug 24 - Aug 25
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

9.2 out of 10, Wonderful, (5)
"Great place to stay very accommodating more than expected "
The price is CA $284
CA $523 total
includes taxes & fees
Aug 25 - Aug 26
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!

The price is CA $237
CA $572 total
includes taxes & fees
Aug 26 - Aug 27
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

The price is CA $458
CA $776 total
includes taxes & fees
Aug 25 - Aug 26
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

September Special! Choose a complimentary fun experience - see details below!

10.0 out of 10, Exceptional, (1)
"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. "
The price is CA $869
CA $1,914 total
includes taxes & fees
Aug 25 - Aug 26
September Special! Choose a complimentary fun experience - see details below!

September Special! Choose a complimentary fun experience - see details below!

10.0 out of 10, Exceptional, (4)
"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"
The price is CA $869
CA $1,914 total
includes taxes & fees
Aug 25 - Aug 26
September Special! Choose a complimentary fun experience - see details below!

September Special! Choose a complimentary fun experience - see details below!

10.0 out of 10, Exceptional, (2)
"We had an absolutely incredible stay at this beautiful Catskills retreat! We booked with Several friends and celebrated their 50th birthday here and it was a wonderful decision. The home was spotless, stylish, and fully equipped with everything we needed for a relaxing and comfortable visit. From the cozy fireplace and spacious deck to the stunning views of the woods and mountains. Set in beautiful and peaceful surroundings, every detail was thoughtfully curated to create the perfect escape....
The price is CA $869
CA $1,911 total
includes taxes & fees
Aug 26 - Aug 27
September Special! Choose a complimentary fun experience - see details below!

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

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

Drift Haus|4.5BR+ Mountain Lodge

The price is CA $1,035
CA $1,785 total
includes taxes & fees
Aug 29 - Aug 30
Drift Haus|4.5BR+ Mountain Lodge

Spacious Catskills Getaway w/ Hot Tub, Deck, Home Theater & Game Room

10.0 out of 10, Exceptional, (16)
"Beautiful home, very spacious, clean, well equipped with everything you need. Everything needed in the kitchen, plenty of linens. We had a wonderful time with our family. Made lots of beautiful memories. The hosts were a pleasure to deal with. Would highly recommend. "
The price is CA $1,078
CA $1,995 total
includes taxes & fees
Sep 8 - Sep 9
Spacious Catskills Getaway w/ Hot Tub, Deck, Home Theater & Game Room

4-bedroom country house in serene Windham with WiFi, AC

The price is CA $553
CA $676 total
includes taxes & fees
Sep 5 - Sep 6
4-bedroom country house in serene Windham with WiFi, AC

Cozy Waterfall Home | Close to All Mountains/Hikes

3.0 star property
10.0 out of 10, Exceptional, (3)
"The host is very responsive and the listing is accurate about what to expect with the property."
The price is CA $142
CA $398 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Waterfall Home | Close to All Mountains/Hikes

Sioux Tipi on Chloe's Lake

9.6 out of 10, Exceptional, (5)
"This was such a cool experience Id love to go back! "
The price is CA $152
CA $201 total
includes taxes & fees
Sep 21 - Sep 22
Sioux Tipi on Chloe's Lake

Jessie's Harvest House

10.0 out of 10, Exceptional, (1)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
The price is CA $149
CA $263 total
includes taxes & fees
Aug 26 - Aug 27
Jessie's Harvest House

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

9.8 out of 10, Exceptional, (20)
"Hidden Gem, very cozy and perfect for a quiet weekend getaway. "
The price is CA $198
CA $435 total
includes taxes & fees
Aug 28 - Aug 29
Free 50 Amp EV Charger Modern New, HotTub, A/C, Webber Grill, 2 Decks, FirePit

Tranquil 2-bedroom house with AC in Cornwallville nestled on 23 acres

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay!"
The price is CA $260
CA $475 total
includes taxes & fees
Aug 24 - Aug 25
Tranquil 2-bedroom house with AC in Cornwallville nestled on 23 acres
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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Top Windham Hotel Reviews