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Vacation Homes in Windham

Find the vacation homes that appeal to you the most

August 2026

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Vacation Homes for every style

Find the right vacation home for you in Windham

The best vacation homes in Windham

Check out our selection of great vacation homes in Windham

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Hunter Mountain Sanctuary

Hunter (Near Windham)

Featuring a garden, Hunter Mountain Sanctuary provides accommodations in Hunter. This property offers access to a terrace and free private parking.

R
Russell
From
United States
There was nothing not to like.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 9 reviews
Price from
$699.10
1 night, 2 adults
Check availability

Amazing Views! Hunter Mt 5 Bedroom Home! Best location surrounded by beautiful Mt views! Enjoy Lakes, Ski Slopes & Firepit under Stars!

Hunter (Near Windham)

Amazing Views! Hunter Mt 5 Bedroom Home! Best location surrounded by beautiful Mt views! Enjoy Lakes, Ski Slopes & Firepit under Stars!

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 6 reviews
Price from
$661.20
1 night, 2 adults
Check availability

Luxe Catskills Mountain Retreat with Private Pool, Pond, Hot Tub, Fire Pit, Dog Friendly

Cairo (Near Windham)

Luxe Catskills Mountain Retreat with Private Pool, Pond, Hot Tub, Fire Pit, Dog Friendly offers accommodations in Cairo, 19 miles from Catskill State Park.

M
Marisa
From
Curaçao
We had a wonderful stay and the hosts did everything to make our stay as comfortable as possible. It felt like being home away from home. This spacious house has everything one could think of and the decoration is detailed and tasteful. The beds are very comfortable. The location is close to ski locations like Windsor, Catskill and Hunter and the supermarket is a short drive away in Cairo. We would love to come back one day!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews
Price from
$566.08
1 night, 2 adults
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Catskill MNTN Escape 5 BR 3 bath Villa Hot Tub Fire Pit Best Group Stay

Prattsville (Near Windham)

16 miles from Hunter Mountain in Prattsville, Catskill MNTN Escape 5 BR 3 bath Villa Hot Tub Fire Pit Best Group Stay features accommodations with access to a hot tub.

C
Christina
From
United States
Absolutely beautiful home we had everything we needed
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 16 reviews
Price from
$1,060.20
1 night, 2 adults
Check availability

Close to skiing and hiking, walk to main street

Tannersville (Near Windham)

Close to skiing and hiking, walk to main street offers accommodations in Tannersville, 12 miles from Catskill State Park and 22 miles from Hudson Athens Lighthouse.

G
Geertsma
From
United States
Enjoyed the Xmas tree, decorations, and the pool table.
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 6 reviews
Price from
$395
1 night, 2 adults
Check availability

The HideAway Tiny Cabin

East Durham (Near Windham)

19 miles from Catskill State Park in East Durham, The HideAway Tiny Cabin features accommodations with access to a public bath and open-air bath.

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 9 reviews
Price from
$365
1 night, 2 adults
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Hunter Haven - Luxury Cabin Near Mountain Ski Resort

Lanesville (Near Windham)

Hunter Haven - Luxury Cabin Near Mountain Ski Resort offers accommodations in Lanesville, 14 miles from Catskill State Park and 26 miles from Hudson Athens Lighthouse.

G
Gloria
From
United States
Great location, big, loved the amenities, hosts were friendly and fast at replying
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 8 reviews
Price from
$575.36
1 night, 2 adults
Check availability

Mountainscape: Peaceful & Skiing

Roxbury (Near Windham)

Mountainscape: Peaceful & Skiing offers accommodations in Roxbury, 29 miles from Catskill State Park and 15 miles from Delaware Ulster Railroad.

K
Kari
From
United States
I spent Christmas at the cabin with my little dog. It was very quiet, cozy and clean. There were enough pans to cook any meals (I did bring a deep baking dish to bake a turkey breast) but there are sauce pans, a baking sheet and skillets. There are a few basic cooking utensils as well. The cabinets were stalked with basic spices, coffee and some tea. The streaming service options were great. The wifi was pretty decent for the location, even though it was cloudy and windy. The heater was great. It did get a little chilly in the bedroom, but I like it cold when I sleep, so I didn't mind. Michael is an amazing communicator and checked in with me to make sure I arrived safely and got in okay. I am sure if there had been an issue, it would have been easy to get a hold of him. There is a great little grocery store 5 minutes away and a gas station. No complaints here and I would stay here again. I chose it for the price (driving an hour further than I planned) but it was worth it. I even bought my pop up Christmas tree to make it festive.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 11 reviews
Price from
$260.35
1 night, 2 adults
Check availability

Redwood Retreat in Windham - Pool! Tennis!

Windham

Offering a seasonal outdoor swimming pool, Redwood Retreat in Windham - Pool! Tennis! features accommodations in Windham.

G
Ghazaal
From
United States
The mountain view was amazing ! The fireplace and soft leather sofa was a relaxing delight!
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 21 reviews
Check availability

High Peak Heaven: Cozy Log Cabin on 1 Acre!

Windham

11 miles from Catskill State Park in Windham, High Peak Heaven: Cozy Log Cabin on 1 Acre! offers accommodations with access to a spa center.

N
Niel
From
United States
Well kept, well equipped and a high quality 👏 👌
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 7 reviews
Check availability
All vacation homes in Windham

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Windham and surrounding area in the past month

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Popular with guests booking vacation homes in Windham

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 21 reviews

Popular with guests booking vacation homes in Windham

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Windham

Popular with guests booking vacation homes in Windham

Popular with guests booking vacation homes in Windham

Popular with guests booking vacation homes in Windham

Popular with guests booking vacation homes in Windham

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Windham

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Windham

Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 4 reviews

Popular with guests booking vacation homes in Windham

Enjoy breakfast in Windham and nearby

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Mountain Cabin with Scenic Views and Hot Tub offers accommodations in Windham, 11 miles from Hunter Mountain. The air-conditioned accommodation is 29 miles from Hudson Athens Lighthouse.

Cozy Rustic Bliss Seconds from Windham Mt Resort offers accommodations in Windham, 11 miles from Hunter Mountain. The air-conditioned accommodation is 29 miles from Hudson Athens Lighthouse.

8.5 miles from Catskill State Park in Windham, Slope Views: Luxe Windham Retreat w/ Hot Tub! provides accommodations with access to a hot tub and spa center.

Scored out of 10, guest rating 6.0
Pleasant - What previous guests thought, 1 review

Windham Home Near Mountain Biking & Hiking Trails! is located in Windham, just 8.9 miles from Catskill State Park and 1.4 miles from Windham Mountain.

30 miles from Hudson Athens Lighthouse in Windham, 'The Mountain House:' Windham Retreat w/ Hot Tub! provides accommodations with access to a hot tub and spa center.

Windham Mountain Vacation Rental ~ 3 Mi to Lifts! offers accommodations in Windham, 10 miles from Catskill State Park and 2 miles from Windham Mountain.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Featuring a garden, Lux Windham Getaway - Views & Indoor Heated Pool provides accommodations in Windham. This vacation home offers air-conditioned accommodations with a patio.

Custom Windham Mtn Villa w/ Pool, Theater & Views! is located in Windham, just 2 miles from Windham Mountain and 12 miles from Zadock Pratt Museum.

Save money on vacation homes in Windham and nearby – budget options available

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2 Mi to Windham Mountain: Scenic Home w/ Fire Pit! offers accommodations in Windham, 8.2 miles from Catskill State Park and 28 miles from Hudson Athens Lighthouse.

Ski, Hike & Golf: Pet-Friendly Windham Retreat offers accommodations in Windham, 10 miles from Catskill State Park and 30 miles from Hudson Athens Lighthouse.

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review

8.7 miles from Catskill State Park in Windham, Cozy Mtn-View Chalet < 2 Mi to Windham Slopes provides accommodations with access to a hot tub.

Romantic Glamping Dome in the Catskill Mountains near Woodstock, New York offers accommodations in Hensonville, 6.4 miles from Catskill State Park and 2.9 miles from Windham Mountain.

Retro Retreat Charming Home with Hot Tub & Fire Pit offers accommodations in Hensonville, 28 miles from Hudson Athens Lighthouse and 9 miles from Hunter Mountain. This vacation home features a garden.

Scored out of 10, guest rating 7.0
Good - What previous guests thought, 1 review

13 miles from Hunter Mountain in Windham, Grand Windham Retreat w/ Fire Pit & Game Room offers accommodations with access to a fitness room.

Offering a garden, Luxurious Home & Amazing Views offers accommodations in Windham. The air-conditioned accommodation is 13 miles from Hunter Mountain.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Windham Retreat w/ Private Deck & Mtn Views! offers accommodations in Windham, 7.2 miles from Catskill State Park and 28 miles from Hudson Athens Lighthouse.

Great access to the city center. Check these vacation homes in Windham and nearby

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Mtn-View Home w/ Deck on 4 Acres in Windham offers accommodations in Windham, 12 miles from Catskill State Park and 28 miles from Hudson Athens Lighthouse.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

12 miles from Catskill State Park in Windham, Mountain Blue Vista - Hot tub, Firepit, 10 acres, perfect location! features accommodations with access to a hot tub.

Vacation Homes with swimming pools in Windham and nearby

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The Hilltop Hideaway by AvantStay is located in Jewett, just 11 miles from Catskill State Park and 7.6 miles from Windham Mountain.

FAQ about vacation homes in Windham

The average price per night for a vacation home in Windham this weekend is $1,123 (based on Booking.com prices).
The average price of a vacation home in Windham this evening is $2,898 (based on Booking.com prices).

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