Windham Holiday Rentals

Compare Villas, Resorts, & Rentals in Windham, New York, USA

Cozy Caboose in the city
FromR3,293 per night
10.0 (107 Reviews)
1 Bedroom 2 Guests
Fantastic 2 family vacation home with EV charger
|
10.0 (3 Reviews)
4 Bedrooms 10 Guests
Antique Rose Inn Windham
FromR2,403 per night
|
9.0 (129 Reviews)
1 Bedroom 2 Guests
Luxury Home with Deck Explore the Catskill Mtns!
|
10.0 (2 Reviews)
4 Bedrooms 8 Guests
Georgian Garden Inn
FromR4,076 per night
|
9.0 (28 Reviews)
1 Bedroom 2 Guests
Gorgeous, First Class, 2 King apartment in downtown Windham
10.0 (15 Reviews)
2 Bedrooms 4 Guests
Mtn-View Home w/Deck on 4 Acres in Windham
|
10.0 (1 Review)
3 Bedrooms 6 Guests
Red Feather Lodge
FromR35,579 per night
|
New
1 Bedroom 2 Guests
Spacious Apt w/Yard: 3 Mi to Windham Mountain
|
10.0 (1 Review)
2 Bedrooms 6 Guests
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
10.0 (10 Reviews)
2 Bedrooms 4 Guests
The Windham A
FromR8,410 per night
10.0 (1 Review)
1 Bedroom 8 Guests
Windham getaway!
FromR3,341 per night
10.0 (10 Reviews)
2 Bedrooms 8 Guests
Cozy, Modern Cabin Retreat 8 min to Windham mtn
10.0 (1 Review)
1 Bedroom 11 Guests
Lake view Cabin on Lake Heloise
10.0 (8 Reviews)
1 Bedroom 5 Guests
Beautiful Windham Chalet 2 minutes to the Mountain
|
9.8 (8 Reviews)
4 Bedrooms 11 Guests
Cozy Cabin Condo by the Mountain, 5mins to skiing!
10.0 (7 Reviews)
1 Bedroom 4 Guests
Windham Ridge Chalet
FromR4,240 per night
|
9.5 (2 Reviews)
3 Bedrooms 5 Guests
Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
10.0 (6 Reviews)
2 Bedrooms 6 Guests
Georgian Garden
FromR2,455 per night
|
9.3 (20 Reviews)
6 Bedrooms 12 Guests
Mountain view apartment, 5mins to Ski Area!
10.0 (6 Reviews)
2 Bedrooms 4 Guests
Redwood Retreat in Windham - minutes to Mtn!
|
9.3 (16 Reviews)
2 Bedrooms 6 Guests
Condo w/Loft: 2 Mi to Windham Mountain Ski!
|
9.2 (8 Reviews)
2 Bedrooms 6 Guests
Relaxing Catskills Apt < 3 Mi to Windham Mountain!
10.0 (2 Reviews)
2 Bedrooms 7 Guests
Lux Windham Getaway - Views & Indoor Heated Pool
|
9.0 (1 Review)
5 Bedrooms 16 Guests
All-Season Condo - Ski Windham l Hunter l Pool l Hike l Fish
10.0 (2 Reviews)
2 Bedrooms 8 Guests
Cozy Catskill Condo - 2 Mi to Windham Mountain Ski
|
8.7 (4 Reviews)
2 Bedrooms 6 Guests
Catskills Townhome about 2 Mi to Windham Mountain Club
|
8.7 (3 Reviews)
3 Bedrooms 8 Guests
Catskills Home, 5 Mins to Windham Mtn Resort!
|
8.6 (7 Reviews)
2 Bedrooms 6 Guests
5 Minutes from Windham Mountain
FromR4,450 per night
10.0 (1 Review)
2 Bedrooms 4 Guests
Vacation Rental Home ~ 2 Mi to Windham Mountain!
|
8.5 (2 Reviews)
3 Bedrooms 9 Guests
Cozy Mountain Condo
FromR3,850 per night
10.0 (1 Review)
2 Bedrooms 7 Guests
Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
|
8.0 (1 Review)
2 Bedrooms 6 Guests
2 Bedroom Townhouse in front of Windham Mountain Ski Resort
9.8 (50 Reviews)
2 Bedrooms 8 Guests
Homey Windham Condo: Hike & Ski the Catskill Mtns!
|
8.0 (1 Review)
2 Bedrooms 4 Guests
Cozy Gateway Gem for 2 at Widham
9.8 (11 Reviews)
1 Bedroom 4 Guests
Woodside Cabin #2 on Lake Heloise
9.8 (7 Reviews)
1 Bedroom 5 Guests
Windham Home Near Mountain Biking & Hiking Trails!
9.8 (7 Reviews)
2 Bedrooms 4 Guests
Redwood Retreat in Windham - minutes to Mtn!
9.6 (63 Reviews)
2 Bedrooms 6 Guests
Catskills Home, 5 Mins to Windham Mtn Resort!
9.6 (17 Reviews)
2 Bedrooms 6 Guests
Modern Windham Retreat w/Hot Tub & Fire Pit
9.6 (7 Reviews)
2 Bedrooms 7 Guests
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
10.0 (110 Reviews)
6 Bedrooms 14 Guests
Grand Windham Retreat w/Fire Pit & Game Room
|
7.0 (1 Review)
2 Bedrooms 6 Guests
Albergo Allegria Hotel
FromR2,895 per night
|
9.6 (278 Reviews)
1 Bedroom 2 Guests
The Cabins at Walnut Grove-minutes from Hunter and Windham
7.0 (1 Review)
1 Bedroom 11 Guests
Hotel Vienna
FromR2,869 per night
|
9.4 (799 Reviews)
1 Bedroom 2 Guests
Townhouse W Private Deck & Mt View
FromR2,966 per night
|
6.8 (9 Reviews)
4 Bedrooms 14 Guests
Cave Mountain Motel
FromR2,474 per night
9.4 (140 Reviews)
1 Bedroom 2 Guests
Windham Home Near Mountain Biking & Hiking Trails!
|
6.0 (1 Review)
2 Bedrooms 4 Guests
Relaxing Catskills Apt < 3 Mi to Windham Mountain!
|
5.0 (2 Reviews)
2 Bedrooms 7 Guests
Windham Family Getaway
FromR4,966 per night
10.0 (53 Reviews)
3 Bedrooms 9 Guests
Beds on Clouds
FromR3,395 per night
|
4.2 (11 Reviews)
8 Bedrooms 28 Guests
Peaceful Catskills Condo with Deck and Mountain View!
3.7 (3 Reviews)
1 Bedroom 2 Guests
'The Mountain House:' Windham Retreat w/Hot Tub!
10.0 (36 Reviews)
4 Bedrooms 8 Guests
Amazing Views Hot Tub Fire Pit Game Room
|
New
1 Bedroom 12 Guests
Windham Private heated indoor pool.
10.0 (28 Reviews)
5 Bedrooms 12 Guests
Slope Views: Luxe Windham Retreat w/Hot Tub!
|
New
5 Bedrooms 17 Guests
River & Golf Mountain Retreat
FromR14,072 per night
10.0 (28 Reviews)
4 Bedrooms 8 Guests
The Windham Mountain House by AvantStay
|
New
4 Bedrooms 8 Guests
EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS
10.0 (25 Reviews)
9 Bedrooms 18 Guests
Cozy Rustic Bliss Seconds from Windham Mt Resort
|
New
5 Bedrooms 8 Guests
"New Home" Idyllic Mt Views ,Pond & Horse farm views 2 min to Town
10.0 (25 Reviews)
4 Bedrooms 10 Guests

About Casai's Private Villas and Holiday Rentals in Windham

Discover more than 441 vacation rentals available in Windham. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windham.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windham, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windham. On average, places to stay near Windham offer 1502.64 ft², with nightly prices averaging R11,918.

With Casai, finding and comparing holiday rentals in Windham is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.