Vacation Home Rentals By Owner In Windham, NY

Showing 125 Of 125 Vacation Rentals

$178.2

2 Bedroom Townhouse in front of Windham Mountain Ski Resort

Windham, New York, United States

This 2 bedroom, 2 bath Townhouse with loft is located at the top of Windham Mt Village a very short easy walking distance from the Windham ski lodge and beginner lifts. The unit sleeps 8 people (max 6 adults + 2 children) total with a master bedroom with Queen Duxiana bed on main floor and 2nd bedroom with 4 bunk beds and a loft with 2 Duxiana twin beds on the upper level. 2 newly rebuilt full baths with showers, fully equipped kitchen, dining area, living area with wood burning fireplace. Firewood is included. Smart TV with cable and wireless internet included. An outdoor deck has a gas grill. Washer and Dryer. Newly installed central wall air conditioning and heating with remote controls. Access to indoor community pool, hot tub and tennis courts when open.

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Exceptional(110)

$1341.0

/ Nightly

Private Vacation Home

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham, New York, United States

Among the nicest properties in Windham. Lovely large home nestled quietly on 12 usable acres with bucolic bridle paths joined to hiking trails. A true feel of Tuscany on the property beginning at the front door. 16' Travertine Dining Island and Professional Kitchen. Seats 14. Wolf Oven / 48” Induction Cooktop. Pickleball /Snowshoe or Cross-Country on the property in Winter. Relax in Spa/Hot Tub /Theatre Room. Prepare meals in professional indoor or outdoor kitchens. The daily rental rate is weekday/weekend driven. HighSeason and Holiday weekends may require 3-4 night minimums respectively. Housekeeping is 275 plus a 500 refundable security deposit.brMountain bike to multiple destinations. Adjacent views to 30 acre horse farm, pond and Ski Windham. Wedding package details available to discuss. Wedding video encompasses two (2) contiguous properties. Ask owner for clarification on pricing for each. HighSeason and Holiday weekends require 3 or 4 night minimums respectively. Limited access to lift tickets during non holiday periods.

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Exceptional(48)

$543.97

/ Nightly

Private Vacation Home

Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!

Windham, New York, United States

Stunning Windham Log Cabin Retreat! This spacious home has 4 bedrooms and 3 and 1/2 bathrooms. Sleeps 8-10 (1 King, 2 Queens, 3 bunk beds plus pull out queen couch). Includes a loft overlooking the great room. Radiant heated floors throughout the house. Kitchen is fully equipped with stainless steel appliances, pots, pans, etc. Master Bath with whirlpool tub. Full basement with Pool table. Large stone fireplace in the living room. Gorgeous views of the slopes. Only 3 minutes from town. Perfect family retreat! Relax around the firepit and enjoy all the activities that Windham has to offer!

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Exceptional(32)

$460.29

/ Nightly

Private Vacation Home

Wonderful mountain home for all of your family adventures!

Windham, New York, United States

Welcome to our cozy mountain retreat! Our beautiful and spacious cabin is perfect for your next getaway. Whether you’re planning a family ski trip, leaf peeping adventure, or a weekend away with friends, this cabin has everything you need for a comfortable and enjoyable stay.brbrOur cabin is ideally located minutes away from Windham Mountain, so you can hit the slopes in no time. brbrBook now and experience the best of what the mountains have to offer and get ready for an unforgettable adventure !

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Exceptional(2)

$1067.4

/ Nightly

Private Vacation Home

Spacious 5BR All-Season Ski-In/Ski-Out Home Modern Renovation & Smart Features

Windham, New York, United States

Experience mountain living at its finest in this ski-on/ski-off, fully renovated 5-bedroom, 4-bathroom home, designed for every season. Whether you’re hosting friends for a lively weekend or seeking a peaceful getaway surrounded by nature, this spacious retreat offers the perfect blend of modern luxury and cozy comfort.brbrInside, you’ll find state-of-the-art appliances, heated bathroom floors, and two inviting great rooms—one upstairs and one downstairs—ideal for entertaining or relaxing after a day on the slopes. The boot room comes complete with a boot warmer to keep your gear ready for the next run.brbrStep outside to the expansive wraparound deck, where you can grill, gather around the firepit, and take in stunning views of the mountain.brbrPerfect for families, couples, or groups, this all-season home offers every comfort you could want—from crisp winter mornings to sun-soaked summer evenings.brbrAddress: 111-2 Clarence D. Lane Road, Winsome Court, Windham, N.Y. 12496.

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Rent a place that suits your needs

Private vacation home

View 123 Private vacation home

Most popular vacation rentals in Windham

Exceptional(2)

$1372.12

/ Nightly

Private vacation home

Catskills Retreat with Theater, Hot Tub and Games

Windham, New York, United States

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Exceptional(2)

$4142.57

/ Nightly

Private vacation home

Luxury Mountain Log Home, Ski-In/Ski-Out to Windham Resort

Windham, New York, United States

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Exceptional(2)

$3844.80

/ Nightly

Private vacation home

EXCLUSIVE, EXQUISITE & UNFORGETTABLE MOUNTAIN OASIS

Windham, New York, United States

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Exceptional(2)

$3371.14

/ Nightly

Private vacation home

Luxurious ski in/out, 3-story chalet directly on the slopes of Windham Mountain

Windham, New York, United States

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Exceptional(2)

$3365.28

/ Nightly

Cabin

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Windham, New York, United States

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Exceptional(2)

$1690.20

/ Nightly

Cabin

Lux Mansion, Windham: Hot Tub, Sauna, Cold Plunge

Windham, New York, United States

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Exceptional(2)

$1656.00

/ Nightly

Private vacation home

Steps away from the magic carpet that brings you right to the lodge!

Windham, New York, United States

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Exceptional(2)

$1560.27

/ Nightly

Private vacation home

Mountain Chalet with Hot Tub & Pool

Windham, New York, United States

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Exceptional(2)

$1478.51

/ Nightly

Private vacation home

Luxe 8BR Windham Lodge | Theater, Walk to Slopes

Windham, New York, United States

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Exceptional(2)

$1068.14

/ Nightly

Chalet

Luxe Lodge w/ Mt View - Hot Tub, Fire Pit, Game Rm, 5 Min to Skiing

Windham, New York, United States

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Bath

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Vacation Home Rentals By Owner In Windham, NY

$178.2

$1341.0

$543.97

$460.29

$1067.4

Rent a place that suits your needs

Most popular vacation rentals in Windham

$1372.12

$4142.57

$3844.80

$3371.14

$3365.28

$1690.20

$1656.00

$1560.27

$1478.51

$1068.14

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