Holiday Rentals in Windham

155 available vacation rental offers

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Windham holiday rentals
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Best family friendly Windham holiday rentals

Among the 155 accommodations in Windham, here are the 4 best family friendly rentals

Wake Up To Mountain Magic Year-round (Hot Tub) - Windham
9.9 78 reviews
Windham
08/19 – 08/23
HK$3436/nighttotal: HK$13744 (4 )

Wake Up To Mountain Magic Year-round (Hot Tub)

1 2
apartment , Windham
This cosy Windham cottage, near Hunter and Windham, New York, is a 7-8 minute drive from both Windham and Hunter Mountain ski resorts.
Sleeping six guests, this fully updated two-bedroom, one-bathroom property boasts a wood-burning stove, hot tub with mountain views, and a private fire pit; nearby Colgate and Silver Lake offer hiking, swimming, kayaking, and fishing opportunities.
Ski Chalet In Windham - Windham
Windham
07/24 – 07/26
HK$4829/nighttotal: HK$9658 (2 )

Ski Chalet In Windham

3 4
chalet , Windham
This Windham lodge is located 3.2 kilometres from Windham Mountain Resort and less than two hours from New York City, offering a convenient escape.
This family-friendly property accommodates seven guests across three bedrooms and two bathrooms, featuring a well-equipped kitchen, a sunken great room with a fireplace, and a finished basement game room with Foosball and karaoke.
Mitchell Hollow Home - Windham
9.6 45 reviews
Windham
06/26 – 07/05
HK$1521/nighttotal: HK$13689 (9 )

Mitchell Hollow Home

1 2
apartment , Windham
This cosy house is located just a few minutes' drive from Windham Mountain and the Main Street, with Hunter Mountain 32km away. It has received excellent ratings for location, cleanliness, and user experience.
The house is ideal for families, with two bedrooms and a capacity of four guests. It comes equipped with a full kitchen, a spacious living area, and a large dining area, plus a range of amenities including a gas-powered fireplace, a Smart TV, and a selection of games for all ages. The large garden offers a barbecue grill, ample parking, and a great hill for sledding.
Luxury Ski In Ski Out Condo + Amenities - Windham
10 9 reviews
Windham
07/24 – 07/26
HK$5592/nighttotal: HK$11184 (2 )

Luxury Ski In Ski Out Condo + Amenities

3 4
apartment , Windham
This three-bedroom apartment is located at the base of Windham Mountain, just a short walk from the ski slopes. The property has consistently received excellent reviews for its location, cleanliness, and overall experience.
The apartment comfortably sleeps eight guests and offers a modern design with high-end finishes. Guests can enjoy a range of amenities, including a heated outdoor swimming pool, two hot tubs, a fitness centre, and a ski locker room with boot warmers.

Best Windham holiday rentals with a fireplace

Cozy Rustic Bliss Seconds From Windham Mt Resort - Windham
Windham
07/24 – 07/26
HK$6305/nighttotal: HK$12610 (2 )

Cozy Rustic Bliss Seconds From Windham Mt Resort

5 4
house , Windham
This five-bedroom Windham house, a short distance from Windham Mountain Resort, is conveniently located 17.7km from Hunter Mountain and 14.2km from Catskill State Park.
The 279 square metre property boasts a fully equipped kitchen, Jacuzzi, garden, and accommodates up to 11 guests, offering free Wi-Fi, and is ideal for families or groups seeking winter sports access nearby.
Modern Mountain View Chalet In Windham - Windham
10 4 reviews
Windham
07/24 – 08/07
HK$4498/nighttotal: HK$62972 (14 )

Modern Mountain View Chalet In Windham

4 2
chalet , Windham
This Windham lodge is situated 5 minutes from Windham Mountain Resort and 15 minutes from Hunter Mountain, offering ski access and proximity to Zoom Flume water park.
This spacious four-bedroom property accommodates up to 10 guests, featuring a modern open-plan layout, a gourmet kitchen, a furnished deck with a fire pit, and high-speed WiFi for a comfortable stay.
Gods Country (3 Bd) Cottage - Windham
9.8 67 reviews
Windham
07/24 – 07/26
HK$2065/nighttotal: HK$4130 (2 )

Gods Country (3 Bd) Cottage

3 4
apartment , Windham
This Windham Mountain area holiday home, sleeping six guests in three bedrooms and two bathrooms, boasts stunning mountain views and is a short drive from Windham village centre and its amenities.
The self-catering property offers a fully equipped kitchen (fridge, microwave, dishwasher), garden, parking, Wi-Fi, and is pet-friendly, ideal for exploring local hiking trails and enjoying nearby skiing and snowboarding at Windham Mountain Resort in winter.
Catskills Home, 5 Mins To Windham Mtn Resort! - Windham
9.6 82 reviews
Windham
08/19 – 08/23
HK$1736/nighttotal: HK$6944 (4 )

Catskills Home, 5 Mins To Windham Mtn Resort!

2 2
house , Windham
This charming house is situated just 5 kilometres from Windham Mountain Resort and 14 kilometres from Catskill State Park, making it an ideal base for exploring the beautiful Catskill region. It has consistently received excellent ratings for its location, cleanliness, and user experience.
The property offers 102 square metres of living space, comfortably accommodating up to 6 guests in its two bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a relaxing terrace, a garden, a spa, and free Wi-Fi, making this a perfect choice for families or groups seeking a comfortable and convenient stay.

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Best Windham holiday rentals with jacuzzi

Cozy Modern: Views, 3 Min Ski, Fire Pit, Game Room - Windham
9.9 35 reviews
Windham
08/19 – 08/23
HK$3581/nighttotal: HK$14324 (4 )

Cozy Modern: Views, 3 Min Ski, Fire Pit, Game Room

1 2
apartment , Windham
Windy Hollow is a spacious holiday home located just 1.3 kilometres from Windham Mountain Club, a short walk from the centre of Windham, and within easy driving distance of other popular Catskill destinations. The property has excellent user, location and cleanliness ratings.
The home is designed to accommodate up to 8 guests and features multiple gathering spaces, a dedicated playroom for children, a fully equipped kitchen and a wood-burning stove. Amenities include a jacuzzi, a garden, parking, internet access and a wraparound deck, perfect for enjoying the views and stargazing.
Modern Windham Retreat W/ Hot Tub & Fire Pit - Windham
9.8 69 reviews
Windham
07/24 – 08/07
HK$2102/nighttotal: HK$29428 (14 )

Modern Windham Retreat W/ Hot Tub & Fire Pit

1 2
apartment , Windham
This modern apartment is located just a short walk from Windham town centre and a minute's drive from Windham Mountain, offering easy access to restaurants, shops and attractions. It boasts excellent user, location and cleanliness ratings.
The apartment has two bedrooms, each with a king-size bed and an ensuite bathroom, comfortably accommodating up to seven guests. Amenities include a fully equipped kitchen, air conditioning, a jacuzzi, a garden, parking, and access to a stream for fishing and swimming.
Cozy Mtn-view Chalet < 2 Mi To Windham Slopes - Windham
9.7 40 reviews
Windham
07/24 – 07/26
HK$3001/nighttotal: HK$6002 (2 )

Cozy Mtn-view Chalet < 2 Mi To Windham Slopes

2 4
cabin , Windham
This Catskills lodge is conveniently located near Windham and Hunter Mountain ski resorts, offering easy access to hiking trails such as Kaaterskill Falls.
The single-storey property sleeps six guests across two bedrooms and one bathroom, boasting a fully equipped kitchen, private hot tub with mountain views, gas fireplace, wood-burning fire pit, and outdoor deck with gas grill; parking is available for three vehicles.
Ski Mountain Chalet W/ Hot Tub, Fireplace, Game Room -Windham Mountain - Windham
9.7 136 reviews
Windham
07/24 – 08/07
HK$8488/nighttotal: HK$118832 (14 )

Ski Mountain Chalet W/ Hot Tub, Fireplace, Game Room -Windham Mountain

6 2
apartment , Windham
This six-bedroom property is situated just 2.1 kilometres from Windham Country Club and 4.3 kilometres from Windham Mountain Resort, offering easy access to both attractions. The property has received excellent ratings for location, cleanliness, and user experience.
The home spans 353 square metres and features a fully equipped kitchen, four bathrooms, a spa tub, a patio, barbecue grills, and a games room. Guests can enjoy a range of amenities including internet access, air conditioning, and parking.

Best Windham holiday rentals with parking

3 Bdrm/2 Bath In Windham Mountain Village Walking Distance To Mountain With View - Windham
9.0 12 reviews
Windham
07/24 – 07/26
HK$6767/nighttotal: HK$13534 (2 )

3 Bdrm/2 Bath In Windham Mountain Village Walking Distance To Mountain With View

3 4
apartment , Windham
This Windham mountain property is situated 2.4km from Windham Country Club, a 15-minute walk from both the Catskill State Park and Windham Mountain Resort.
This four-bedroom, two-bathroom holiday home sleeps nine guests and boasts an indoor pool, hot tub, tennis court, BBQ grills, fully equipped kitchen, and fireplace; enjoy nearby hiking, skiing, and other outdoor activities.
Vacation Rental Home ~ 2 Mi To Windham Mountain! - Windham
9.6 29 reviews
Windham
06/26 – 07/05
HK$1759/nighttotal: HK$15831 (9 )

Vacation Rental Home ~ 2 Mi To Windham Mountain!

3 2
apartment , Windham
This spacious Windham holiday home is situated near Windham Mountain and approximately 16km from Hunter Mountain, offering convenient access to both ski resorts.
Sleeping up to nine guests, this three-bedroom, one-and-a-half-bathroom property boasts a fully equipped kitchen, sunroom with mountain views, fireplace, and pet-friendly accommodation (additional charge applies); July 4th fireworks are visible from the property.
Great For Families & Groups! - Windham
9.6 8 reviews
Windham
07/24 – 07/26
HK$6479/nighttotal: HK$12958 (2 )

Great For Families & Groups!

4 4
apartment , Windham
This family-friendly house is located in the mountains of Windham, just 3.2 kilometres from Windham Mountain Resort and Windham Country Club, and within a 19.3 kilometre radius of Zoom Flume and Mountain Top Arboretum. The property has received excellent user ratings, reflecting its comfortable and enjoyable atmosphere.
This spacious house can accommodate up to 12 guests and features four bedrooms and two bathrooms. It offers a fully equipped kitchen, a relaxing garden with a terrace, and free WiFi, ensuring a comfortable and enjoyable stay for all.
Beautifully Restored 6br In The Heart Of Windham - Windham
9.8 27 reviews
Windham
07/24 – 07/26
HK$7105/nighttotal: HK$14210 (2 )

Beautifully Restored 6br In The Heart Of Windham

6 4
apartment , Windham
This six-bedroom apartment is situated in Windham, less than 1.6 kilometres from Windham Mountain and within walking distance of Main Street's restaurants, coffee shops, and wine bars. The property offers spacious accommodation for up to 13 guests, with a fully equipped kitchen, a large family room, and a garden.
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