Windham Vacation Rentals - HolidayHomes base64Hash Windham Vacation Rentals - HolidayHomes

Windham Vacation Rentals

Browse 470 available vacation homes and compared across 7 trusted partners

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Top-Rated Vacation rentals in Windham

Book the highest-rated Windham vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Lodge Windham
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
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House Windham
Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub
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House Windham
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
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House Windham
House with terrace & garden
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House Windham
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
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House Windham
Child-friendly house with pool & terrace | Mountain view
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House Windham
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
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House Windham
Vacation home with heated pool, patio & barbeque | Mountain view
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House Windham
House with terrace, garden & BBQ | Mountain view
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Chalet Windham
Chalet with BBQ, hot tub & garden | Perfect for remote work
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House Windham
Luxury Home on Windham Mountain! Walk to Slopes
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House Windham
Windham Private heated indoor pool.
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House Windham
Vacation home with terrace, garden & barbeque | Mountain view | Good for workation
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House Windham
"New Home" Idyllic Mt Views, Pond & Horse farm views 2 min to Town
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House Windham
House with pool, barbeque & patio | Mountain view
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Top 15 most Recommended Vacation Rentals in Windham

Discover your ideal Windham vacation rental with real-time comparisons of 470 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

Chalet Windham
Chalet ∙ 8 guests ∙ 4 bedrooms

Chalet with garden, barbeque & pool

Windham, Greene County, New York, United States
This cozy chalet in Windham accommodates 8 guests and features a relaxing hot tub for your enjoyment.
from $555
per night
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Cabin Windham
Cabin ∙ 5 guests ∙ 1 bedroom

Cabin with jacuzzi | Mountain view

Windham, Greene County, New York, United States
This cozy cabin in Windham accommodates 5 guests and features a relaxing hot tub with stunning mountain views.
from $286
per night
(18)
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House Windham
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented big house with pool, barbecue & jacuzzi | Ski nearby | Pets are welcome

Windham, Greene County, New York, United States
Spacious house rental in Windham for 8 guests featuring a family-friendly kitchen and ample parking for your convenience.
from $510
per night
(12)
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House Windham
House ∙ 10 guests ∙ 5 bedrooms

Children-friendly spacious house with grill, terrace & pool

Windham, Greene County, New York, United States
This house rental in Windham accommodates 10 guests and features a spacious yard perfect for family gatherings.
from $823
per night
(22)
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House Windham
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped house with pool, barbecue & patio | Mountain view | Close to the ski

Windham, Greene County, New York, United States
This spacious house rental in Windham accommodates 8 guests and features a relaxing hot tub for your enjoyment.
from $467
per night
(24)
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House Windham
House ∙ 8 guests ∙ 4 bedrooms

Fully equipped pleasant vacation home with BBQ, jacuzzi & terrace | Mountain view

Windham, Greene County, New York, United States
This house rental in Windham accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $419
per night
(9)
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Chalet Windham
Chalet ∙ 8 guests ∙ 3 bedrooms

Chalet with barbecue & yard | Mountain view

Windham, Greene County, New York, United States
This cozy chalet in Windham accommodates 8 guests and features a charming fireplace for a warm retreat.
from $205
per night
(10)
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House Windham
House ∙ 7 guests ∙ 2 bedrooms

Vacation home with BBQ, hot tub & yard

Windham, Greene County, New York, United States
This house rental in Windham accommodates 7 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $315
per night
(13)
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House Windham
House ∙ 11 guests ∙ 4 bedrooms

Vacation home with sauna, jacuzzi & patio

Windham, Greene County, New York, United States
This house rental in Windham accommodates 11 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $922
per night
(33)
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