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Holiday Houses in Windham

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188 Holiday homes

Brand new 4-bedroom ski chalet with bucolic mountain, lake and meadow views.

Windham house

4 bedrooms / 3 bathrooms / sleeps 10

from £712 / night

£3,348 / week

Two-Story, 3-Bedroom Family Home

Windham house

3 bedrooms / 1 bathroom / sleeps 4

from £177 / night

£882 / week

Catskill Bungalow, Tiny House, Cozy Getaway Cabin for 2 by Hunter and Windham

Windham log cabin

1 bedroom / 1 bathroom / sleeps 2

39

Responds fast! avg. 53 minutes

Travellers’ Choice award

from £66 / night

£481 - £523 / week

24

Responds fast! avg. 53 minutes

Travellers’ Choice award

from £75 / night

£523 - £1,310 / week

Secluded Charming Water Front Log Home

Windham house

4 bedrooms / 2 bathrooms / sleeps 15

6

Travellers’ Choice award

from £314 / night

£2,008 / week

The Mountain House: The Perfect 4 Season Retreat

Windham chalet

8 bedrooms / 7 bathrooms / sleeps 22

from £2,353 / night

£16,470 / week

Windham Mountain Ski House with Great Views

Windham house

3 bedrooms / 2 bathrooms / sleeps 8

from £336 / night

£2,096 - £2,683 / week

***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

Windham house

2 bedrooms / 2 bathrooms / sleeps 5

1

Responds fast! avg. 2 hours 8 minutes

from £156 / night

£1,091 / week

Mountain House Retreat

Windham house

5 bedrooms / 2 bathrooms / sleeps 10

6

from £251 / night

£1,757 / week

*4 Season Nirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw

Windham house

4 bedrooms / 2 bathrooms / sleeps 8

40

Responds fast! avg. 1 hour 11 minutes

Travellers’ Choice award

from £147 / night

£1,025 / week

Windham Mountain Ski House

Windham house

5 bedrooms / 4 bathrooms / sleeps 10

from £471 / night

£5,648 / week

Chickadee Chalet

Windham apartment

2 bedrooms / 1 bathroom / sleeps 4

from £305 / night

£1,913 / week

The Xenia

Windham house

4 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 1 hour 21 minutes

from £420 / night

£2,940 / week

Catskill Domeo - Romantic and Magical Geodesic Glamping Dome in the Catskills!

Windham tented camp

1 bedroom / 1 bathroom / sleeps 4

6

Responds fast! avg. 53 minutes

Travellers’ Choice award

from £82 / night

£569 - £942 / week

The Presidential Suite at Brie & Bordeaux

Windham apartment

3 bedrooms / 2 bathrooms / sleeps 6

1

from £184 / night

£628 / week

Cristal pound at Windham ski resort

Windham condo

4 bedrooms / 4 bathrooms / sleeps 10

from £168 / night

£837 / week

WINDHAM MAGNIFICENT HOLIDAY GETAWAY

Windham house

5 bedrooms / 4 bathrooms / sleeps 18

3

Responds fast! avg. 3 hours 6 minutes

from £759 / night

£5,313 / week

7

Responds fast! avg. 53 minutes

from £66 / night

£481 - £669 / week

Catskills House w/Yard, 1Mi to Windham Mtn Resort!

Windham house

6 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 14 minutes

from £176 / night

£1,231 / week

NEW! Condo w/Loft: 2 Miles to Windham Mountain Ski

Windham condo

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 22 minutes

from £118 / night

£820 / week

Spacious House - 1 Mi. to Windham Ski Resort!

Windham house

5 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 37 minutes

from £157 / night

£1,096 / week

Luxe Family Home 2Mi to Windham Mountain & Resort

Windham house

4 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 14 minutes

from £302 / night

£2,115 / week

'Windham Manor' on 45 Acres - 5 Mi. to Ski Resort!

Windham house

12 bedrooms / 10 bathrooms / sleeps 33

5

Responds fast! avg. 37 minutes

from £1,895 / night

£13,262 / week

Luxe Windham Home w/Hot Tub - Walk to Ski Resort!

Windham house

8 bedrooms / 3 bathrooms / sleeps 17

Responds fast! avg. 1 hour 14 minutes

from £416 / night

£2,912 / week

Tentrr Signature Site - Pleasant Valley Maplecroft Camp

Windham tented camp

1 bedroom / 1 bathroom / sleeps 6

from £92 / night

£779 / week

NEW! Cozy Condo: Hike & Ski the Catskill Mountains

Windham condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 14 minutes

from £118 / night

£820 / week

Modern Home w/ Deck, 5 Minutes to Windham Resort!

Windham house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 14 minutes

from £149 / night

£1,043 / week

Restored Firehouse w/Theater & Private Lake Access

Windham townhouse

4 bedrooms / 2 bathrooms / sleeps 18

3

Responds fast! avg. 1 hour 14 minutes

from £863 / night

£6,040 / week

Amazing 4 BR on Windham

Windham villa

4 bedrooms / 4 bathrooms / sleeps 8

1

from £231 / night

£1,614 / week

'The Mountain House' Windham Retreat w/ Hot Tub!

Windham house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 5 minutes

from £481 / night

£3,363 / week

Luxury Home w/ Deck: Explore the Catskill Mtns!

Windham house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 0 minutes

from £354 / night

£2,478 / week

Great rentals within 20 miles that match your search

Catskill Mountainside Retreat

West Kill house

4 bedrooms / 4 bathrooms / sleeps 10

1

from £470 / night

£3,289 / week

A Stunning Upstate New York Property.

Westerlo house

4 bedrooms / 3 bathrooms / sleeps 8

from £893 / night

£6,248 / week

Perfect weekend away

Hunter chalet

3 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 51 minutes

from £165 / night

£1,200 / week

Hunter / Windham Catskills Getaway

Jewett house

3 bedrooms / 2 bathrooms / sleeps 7

1

from £160 / night

£1,120 / week

Charming Chalet, Fire Pit, The Perfect Getaway

Hunter chalet

3 bedrooms / 1 bathroom / sleeps 6

1

Responds fast! avg. 51 minutes

from £189 / night

£1,412 / week

Meadows, Birdsong, Peace and Quiet

Medusa house

2 bedrooms / 1 bathroom / sleeps 3

from £142 / night

£753 / week

Charming Converted Barn On 2+ Acres Walk To Town

Woodstock house

5 bedrooms / 2 bathrooms / sleeps 10

from £400 / night

£1,883 / week

Woodstock Carriage House

Woodstock house

4 bedrooms / 2 bathrooms / sleeps 6

from £212 / night

£1,412 - £1,742 / week

Windham Skiers Book Now! Cottage North Catskills

Greenville cottage

2 bedrooms / 1 bathroom / sleeps 7

from £273 / night

£989 - £1,779 / week

Viewing 40 of 188
rentals in Windham