20 Best Windham Apartments on Holiday Lettings - Condos

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23 Vacation rentals

(1) Excellent 

26

Windham Vacation home rental

Catskill Region / Windham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
Available for weekends and short-term rentals during Spring, Summer, & Fall. ***Full season rental only in winter. $8500 from 12/1-4/1, not including utilities. $750 refundable damage deposit. One pet allowed.*** Charming and cozy 2 bedroom/2 bathroom house with gorge …see more

from $225 / night

$1575 / week

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from $225 / night

(28) Excellent 

Certificate of Excellence

24

Windham Vacation home rental

Catskill Region / Windham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 18 mi
  • Child friendly
  • Air conditioning
WELCOME HOME TO YOUR OASIS AWAY FROM IT ALL! Le Chalet Montreuil is set up as a TRUE SECOND HOME FURNISHED with all that you need and want for the entire length of your stay. There is no reason to ever leave the COMFORTS & CONVENIENCES of the chalet, if you so desired …see more

Certificate of Excellence

from $375 / night

$1895 - $2895 / week

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Responds fast!
avg. 36 minutes

from $375 / night

(3) Excellent 

22

Home accommodation in Windham

Catskill Region / Windham

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Mountain House Retreat is situated on 7 beautiful acres in the Catskill mountains with panoramic views, a private fresh water pond and lovely forest landscape. This fully furnished mountain house, has an open living space with fireplace. 5 bedrooms, 2 baths, interne …see more

from $300 / night

$2100 / week

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Responds fast!
avg. 3 hours 35 minutes

from $300 / night

(3) Excellent 

15

Vacation cottage in Windham

Catskill Region / Windham

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Nestled on three acres of land with a panoramic view of the Catskill Mountain the Mountain Treasure Two-Bedroom Cottage is the ideal place to take in Mother Nature. Beautiful stream and an open space make this setting a truly magnificent place. This 2 level fully fur …see more

from $249 / night

$1300 / week

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Responds fast!
avg. 2 hours 49 minutes

from $249 / night

(1) Excellent 

23

Windham ski home to rent.

Catskill Region / Windham

3 10 2 nights min

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
This property is located on 5 natural acres, in the majestic Catskill Mountains. The house itself is overlooking a 1 acre spring-fed pond. Kayak, fish, or swim out to the floating dock, or just relax on the deck overlooking the pond. Some of the amenities include: wood …see more

from $300 / night

$1820 - $3220 / week

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Responds fast!
avg. 3 hours 7 minutes

from $300 / night

23

Windham Vacation home rental

Catskill Region / Windham

5 15 2 nights min

  • 5 bedrooms
  • Sleeps 15
  • 2 nights min
  • Child friendly
  • Pet friendly
Beautiful five bedroom home on three acres backing up to a stream. Four bedrooms on ground level and Master Bedroom on second floor with his and her bathrooms. Basement is newly refinished gameroom with brand new pool table, foosball, ping pong, card table, darts, and a …see more

from $500 / night

$3500 / week

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Responds fast!
avg. 3 hours 4 minutes

from $500 / night

(4) Good 

17

Windham Vacation apartment rental

Catskill Region / Windham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets
Cozy, two bedroom apartment, ideal for couples or family. Beds: 1 queen, two singles. Stones throw from Ski Windham, 7 miles to Hunter Mountain. Located in Hensonville (part of Windham, NY) Walking distance to grocery, diner, 4 star restaurant, bar and lounge. Off …see more

from $75 / night

$498 - $777 / week

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Responds fast!
avg. 40 minutes

from $75 / night

(1) Excellent 

9

Vacation apartment in Windham

Catskill Region / Windham

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
An upscale and contemporary suite located in the heart of the Catskills, above Bistro Brie & Bordeaux, on Main Street, in Windham, NY. Create you getaway weekends, weeks and season stays. The suite has a king bed, queen bed, and one bunk bed. The great room, incorporat …see more

from $425 / night

$2975 / week

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from $425 / night

12

Ski apartment to rent in Windham

Catskill Region / Windham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Ski
2015 Ski Season rental available. Located 5 minutes from Windham Mountain Ski Resort. The apartment features 2 bedrooms, one bath, furnished with quaint country antiques, and new furniture. Spotlessly clean, convent. The kitchen is fully equiped with dishes, utensils, p …see more

from $350 / night

$2200 / week

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from $350 / night

7

Windham ski home to rent.

Catskill Region / Windham

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Ski
  • Child friendly
Gorgeous Windham Mountain home with spectacular views (sleeps up to 14). Celebrate Thanksgiving, Christmas (through 12/29) and other weekends/weeks in November and December (2 night minimum). Ski in/ski out-snow permitting.But regardless, blissful, idyllic relaxation g …see more

from $800 / night

$5600 / week

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from $800 / night

16

Vacation home in Windham

Catskill Region / Windham

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly
The chic, laid-back beauty and authentic comfort of our farm, house & gardens, will inspire you! Enjoy the soothing, peaceful and relaxing rural countryside. Just 25 min. driving to Albany and 35 min. to Hudson. - THE HOUSE .- Originally built in the mid to late 19th C …see more

from $750 / night

$3951 / week

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from $750 / night

24

Vacation home in Windham

Catskill Region / Windham

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Comfortable, two-story, 7-room family home on an acre of land. Recently redecorated, new carpeting, new appliances. Master bedroom has king-size bed, 2nd and 3rd bedrooms each have a twin bed. Living Room, separate Dining Room, Kitchen, and Playroom. Full Bath. Front an …see more

from $200 / night

$1000 / week

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from $200 / night

(2) Very Good 

20

Windham Vacation townhouse rental

Catskill Region / Windham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Spacious 2 bedroom apartment with queen size beds great for couples or a family with beautiful natural lighting located in scenic Prattsville, NY. Two levels. Downstairs: full kitchen, living room, flat screen TV, half bath (sink, toilet, washer/dryer). Upstairs: two …see more

from $75 / night

$498 - $847 / week

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Responds fast!
avg. 40 minutes

from $75 / night

14

Home rental in Windham

Catskill Region / Windham

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
This is a cozy 3 bedroom Cape Cod with open loft and skylights. Less than 1 mile to Hunter Mountain! Great for Festivals! Wooded end of road location with Apple Trees during season. Stone wood-burning fireplace in living room, deck for outdoor dining in the front of the …see more

from $300 / night

$1000 / week

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from $300 / night

20

Windham Vacation home rental

Catskill Region / Windham

3 9 2 nights min

  • 3 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
Great views of Windham Mountain and the valley left and right. The house is 1.3 miles from Ski Windham. Large living room/dinning area with birds eye view of mountain and valley from a wraparound deck. Enjoy an adult cocktail watching the New Years Fire works or the sta …see more

from $350 / night

$2450 / week

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from $350 / night

(3) Excellent 

54

Ski home to rent in Windham

Catskill Region / Windham

5 14 2 nights min

  • 5 bedrooms
  • Sleeps 14
  • 2 nights min
  • Ski
  • Child friendly
We are looking for families to treat this nice place like their own. Enjoy some quality time with family and friends!One of the loveliest homes in Windham not only for its quality and style but for its direct views of Windham Mt ski slopes. Views are so spectacular they …see more

from $899 / night

$6293 / week

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from $899 / night

45

Windham ski home to rent.

Catskill Region / Windham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ski
  • Child friendly
  • Air conditioning
Located in windham just 3- miles from town. Luxury home on 4-fenced acres overlooking the lake, farm meadow and the Thomas cole mountain range. 4-bdrms, 3-baths, 20' vaulted open living, dining and kitchen with fireplace. Finished lower level with billiard table, TV and …see more

from $550 / night

$3000 / week

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Responds fast!
avg. 30 minutes

from $550 / night

14

Vacation home in Windham

Catskill Region / Windham

4 13 2 nights min

  • 4 bedrooms
  • Sleeps 13
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Wake up to amazing views of Windham Mountain & enjoy the peace and quiet that surrounds you. The house sits on 15 beautiful acres. You will enjoy absolute privacy. You can explore on property. There is a private pond where you can fish. Also tons of nearby activities wh …see more

from $290 / night

$2030 / week

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Responds fast!
avg. 2 hours 29 minutes

from $290 / night

8

Windham Vacation condo rental

Catskill Region / Windham

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
This amazing 4 bedroom apartment is located at Crystal Pond Condos in Windham near the ski resort on Windham Mountain. you can rent for Thanksgiving till end of March including the new year and Christmas. Free transportation is provided from the condo to the ski resort …see more

from $200 / night

$1000 / week

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from $200 / night

34

Windham ski chalet to rent.

Catskill Region / Windham

8 22 3 nights min

  • 8 bedrooms
  • Sleeps 22
  • 3 nights min
  • Ski
  • Child friendly
  • Air conditioning
Welcome to the Mountain House. Sitting on five beautiful acres with views of 4 of the highest peaks in the Catskills, this is the perfect family getaway spot for all seasons. Ask about All-Inclusive Packages, which can include, on-site concierge, car and chef services …see more

from $2500 / night

$17500 / week

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from $2500 / night

21

Vacation chalet rental

Catskill Region / Windham

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Air conditioning
Great Fall Getaway!!! Call or email now for last minute tour of Catskills reservation!! This home is a super immaculate, upscale, classic ski chalet nestled on 1 private wooded acre. Home features 3 bedrooms and 2 full baths and comfortably sleeps 4 adults and 4 childr …see more

from $400 / night

$2400 / week

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Responds fast!
avg. 3 hours 29 minutes

from $400 / night

9

Vacation home in Windham

Catskill Region / Windham

5 10 90 nights min

  • 5 bedrooms
  • Sleeps 10
  • 90 nights min
  • Child friendly
  • Private garden
Large beautiful home on 6 acres of land only a couple minutes to Ski Windham Mountain and snow tubing park. Large outdoor fire-pit surrounded by huge rocks with Adirondack chairs. Nice outdoor hot tub. Out side cooking grill and outside deck looking at Ski Windham Moun …see more

from $500 / night

$6000 / week

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from $500 / night

(1) Excellent 

14

Vacation apartment in Windham

Catskill Region / Windham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
Beautifully decorated & spacious lower level apt in a new log home in Windham, NY. It comes fully equipped & is conveniently located near town, close to restaurants & bars, golf courses, a mountain bike park, walking & hiking trails, lakes for kayaking, tubing, & sailin …see more

from $200 / night

$1400 / week

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Responds fast!
avg. 3 hours 34 minutes

from $200 / night