A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Windham Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Windham holiday rentals

Exterior

1. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (62 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is HK$1,020
HK$1,746 total
includes taxes & fees
18 Aug - 19 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

2. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is HK$745
HK$1,229 total
includes taxes & fees
23 Aug - 24 Aug
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
1 bedroom, in-room safe, iron/ironing board, travel cot

3. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
Windham
8.0 out of 10, Very good, (2 reviews)
"This apartment is comfortable, clean and very good location. The hot tub is a plus with the beautiful view. "
United States
Evelyn
The price is HK$1,228
HK$1,601 total
includes taxes & fees
18 Aug - 19 Aug
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitchen - Haus Windham
Exterior

4. Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is HK$1,281
HK$4,486 total
includes taxes & fees
8 Sept - 9 Sept
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
TV, fireplace

5. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is HK$1,766
HK$4,424 total
includes taxes & fees
14 Sept - 15 Sept
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Dining

6. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is HK$2,013
HK$4,801 total
includes taxes & fees
16 Sept - 17 Sept
2 Min Walk to Windham Town | Hot Tub | Fire Pit
In-room safe, bed sheets

7. MIRROR CABIN IN THE FOREST WITH HOT TUB

MIRROR CABIN IN THE FOREST WITH HOT TUB
Windham
8.0 out of 10, Very good, (4 reviews)
"This was a unique and fun VRBO experience. The cabin was cozy and comfortable.So delightful to wake up to deer walking right by the window! Absolutely a gem of a property!"
United States
Erin J.
The price is HK$1,718
HK$2,222 total
includes taxes & fees
9 Sept - 10 Sept
MIRROR CABIN IN THE FOREST WITH HOT TUB
Exterior

8. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is HK$1,726
HK$4,458 total
includes taxes & fees
9 Sept - 10 Sept
Pines Vignette • Modern 3BR Home in Windham
Outdoor dining

9. 'The Mountain House:' Windham Retreat w/ Hot Tub!

'The Mountain House:' Windham Retreat w/ Hot Tub!
Windham
10.0 out of 10, Exceptional, (36 reviews)
"Great stay Very comfortable "
United States
Teresa G.
The price is HK$2,794
HK$6,348 total
includes taxes & fees
23 Aug - 24 Aug
'The Mountain House:' Windham Retreat w/ Hot Tub!
Interior

10. 'the Mountain House:' Windham Retreat w/ Hot Tub!

'the Mountain House:' Windham Retreat w/ Hot Tub!
3.0 star property
Windham
The price is HK$3,343
HK$6,202 total
includes taxes & fees
23 Aug - 24 Aug
'the Mountain House:' Windham Retreat w/ Hot Tub!
Smart TV, fireplace, DVD player, books

11. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
United States
John K.
The price is HK$3,157
HK$5,350 total
includes taxes & fees
15 Sept - 16 Sept
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Smart TV, fireplace

12. Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (16 reviews)
"Location is great"
United States
Jennifer M.
The price is HK$5,218
HK$8,136 total
includes taxes & fees
19 Aug - 20 Aug
Condo in Windham Mountain Village
Coffee/tea maker, fridge, microwave, oven

13. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Windham
7.6 out of 10, Good, (5 reviews)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
The price is HK$1,228
HK$1,601 total
includes taxes & fees
18 Aug - 19 Aug
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
Dining

14. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
10.0 out of 10, Exceptional, (9 reviews)
"Great for two families. The main room is awesome to hang out in. The house is clean, and the owner super helpful."
United States
Michael L.
The price is HK$7,133
HK$14,128 total
includes taxes & fees
15 Sept - 16 Sept
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Smart TV, fireplace

15. LUXURY DUPLEX SUITE WITH JACUZZI

LUXURY DUPLEX SUITE WITH JACUZZI
Windham
The price is HK$1,475
HK$1,909 total
includes taxes & fees
19 Aug - 20 Aug
LUXURY DUPLEX SUITE WITH JACUZZI
Interior

16. LUXURY DUPLEX SUITE WITH JACUZZI

LUXURY DUPLEX SUITE WITH JACUZZI
Windham
The price is HK$1,475
HK$1,918 total
includes taxes & fees
18 Aug - 19 Aug
LUXURY DUPLEX SUITE WITH JACUZZI
1 bedroom, in-room safe, iron/ironing board, travel cot

17. PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY

PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
Windham
The price is HK$1,640
HK$2,123 total
includes taxes & fees
9 Sept - 10 Sept
PRESIDENTIAL DUPLEX SUITE WITH HOT TUB AND WRANP AROUND BALCONY
1 bedroom, in-room safe, free WiFi, bed sheets

18. GLASS MIRROR CABIN - HAUS WINDHAM

GLASS MIRROR CABIN - HAUS WINDHAM
Windham
8.0 out of 10, Very good, (1 review)
The price is HK$1,640
HK$2,132 total
includes taxes & fees
18 Aug - 19 Aug
GLASS MIRROR CABIN - HAUS WINDHAM
Dining

19. NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham

NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
Windham
8.0 out of 10, Very good, (2 reviews)
"There is obviously a lot to of remodeling and upgrades going on. New hot tub was not installed. Bathrooms, beds and kitchen were nice. Floors and windows were very dirty. There were no bath washcloths. Perhaps they are not included. The wood exterior side walk is dangerous and needs replaced."
United States
Jackie S.
The price is HK$1,640
HK$2,106 total
includes taxes & fees
8 Sept - 9 Sept
NEW OUTDOOR HOT TUB! Luxury 2 Bedroom Suite -The Haüs Windham
Interior

20. The Haüs Windham - Luxury 2 Bedroom Suite w Loft

The Haüs Windham - Luxury 2 Bedroom Suite w Loft
Windham
4.0 out of 10, (1 review)
"Good last minute ski accommodation"
United States
Adam D.
The price is HK$1,804
HK$2,346 total
includes taxes & fees
31 Aug - 1 Sept
The Haüs Windham - Luxury 2 Bedroom Suite w Loft
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windham Hotel Reviews

Emerson Resort & Spa

Emerson Resort & Spa

10/10 Excellent
"Staff was amazing especially at the restaurant which was right next to our lodge never left the property in 4 days that we stayed there other guests were very friendly and everyone seemed just to want to relax would definitely go back"
Brian 3-night trip
Posted 1 hour ago
Emerson Resort & Spa

Find out more about Windham

Search for holiday rentals in Windham on Expedia! You can easily find your home rentals, villas, holiday apartments in Windham using one of the methods below:

  • View our selection of featured holiday rentals in Windham
  • Use the map to find apartments and other holiday homes in the Windham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windham while they last

Look no further and take a look at our great range of rental properties in Windham!

Frequently asked questions

Can I find holiday rentals in Windham?

Yes, there are holiday rentals close to the most popular sights in Windham, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Windham is known for its ski slopes and mountain landscape. While you're here, grab a bite or have a drink at the coffee shops.

What are some of the best holiday rentals that Windham has to offer?

Catskill Mountain Retreat -- private, beautiful views, hot tub, game rm, firepit: This holiday home rental outside of Windham is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a library and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Windham?

With 141 Expedia holiday rentals, you're guaranteed to find just the right place for your Windham stay.

What can I see and do in Windham?

Elm Ridge Wild Forest and Ashland Park are a couple of lovely local spots to get outside and enjoy nature. Windham Country Club and Windham Mountain Resort are other places to visit while you're in town.

What are holiday rentals like in Windham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windham. Holiday rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.