Holiday rentals in Windham

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Top-rated holiday rentals in Windham

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Chalet in Windham
Beautiful Windham Ski/Summer House
A spacious 4 bedroom house located in Windham, NY just 5 minutes from the mountain. Built in 2012. Brand new comfy couches just purchased March 2021. Beautifully decorated with large wood doors, stone fireplace, and granite countertops. Wake up to view of the slopes from the large windows. Truly breathtaking views year round. Four bedrooms three with queen beds and 1 with a bunk beds (full size beds/twin trundle on the bottom). Plus a couch located in the loft area. The house sleeps 12. Full basement with television and couch with a ping pong table, a basketball game and a fooseball table. There are 3 full bathrooms along with one half. The main floor has a fire place along with tv and a full kitchen and dining area all with full views of Windham mountain. Come see the leaves turn and enjoy Great hiking, biking, golf and skiing when the snow comes. One mile from town and Windham Mountain. Pricing for a week goes from Friday to Friday. Renters must be at least 25 years old. Please no pets are allowed at the house, this is a strict policy no exceptions. No parties allowed Cleaning fee additional Christmas and New Years week have a 4 day min. and MLK and Presidents day week have a 3 day min.
21–28 MayIndividual Host,
£410 per night
4.87 out of 5 average rating, 181 reviews
Guest favourite
Cabin in Durham
Stunning Cabin, Sauna, HT, MtnView, Mins 2 Windham
Welcome to Chalet LaRosa, a new 2,450 SF custom cabin just 10 minutes from Windham Mountain & easily accessible to the area's hottest attractions! This idyllic 4BR, 3BA retreat w/ an 8" cedar sauna, hot tub, & full game/bar area is situated on the Durham Scenic Byway w/ some of the Catskills' most breathtaking views. The cabin provides a rare amenity package & truly authentic Catskills experience w/ decor & materials sourced from dozens of local shops & antique collectors. Come enjoy the Chalet!
3–10 Jul
£590 per night
4.99 out of 5 average rating, 111 reviews
Superhost
Cabin in Maplecrest
The Cabin - Ski House near Windham
The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.
8–15 AugIndividual Host,
£359 per night
4.95 out of 5 average rating, 166 reviews

Popular amenities for Windham holiday rentals

Stay near Windham's top sights

Chicken Run Family Restaurant and Steak House214 locals recommend
Michael's Diner- Now Windham Diner53 locals recommend
Catskill Mountain Country Store - Windham105 locals recommend
The Windham Local129 locals recommend
Millrock Restaurant105 locals recommend
Tap House Grille72 locals recommend

Other great holiday rentals in Windham

Guest favourite
Holiday home in Windham
Farmhouse Chic with Mountain and Lake Views
18–25 AugIndividual Host,
£403 per night
4.93 out of 5 average rating, 55 reviews
Guest favourite
Guest house in Windham
Alpine Chalet on Spectacular Property
16–23 MayIndividual Host,
£174 per night
5.0 out of 5 average rating, 85 reviews
Guest favourite
Home in Windham
Bluebird Cabin: Modern Home With Ski Windham View
28 Jan – 4 Feb
£316 per night
4.96 out of 5 average rating, 50 reviews
Guest favourite
Townhouse in Windham
Cozy, peaceful-3Br (5 beds)2.5 Bath townhouse
10–17 Apr
£161 per night
5.0 out of 5 average rating, 56 reviews
Guest favourite
Flat in Windham
Black Dome - a 2B, 2B Condo 5 min from Windham Mt.
5–12 AprIndividual Host,
£104 per night
5.0 out of 5 average rating, 16 reviews
Guest favourite
Chalet in Windham
Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing
16–23 MayProfessional Host,
£534 per night
4.99 out of 5 average rating, 78 reviews
Guest favourite
Home in Durham
Wow! Panoramic Mountain View, Minutes to Windham!
8–15 Nov
£221 per night
4.97 out of 5 average rating, 99 reviews
Guest favourite
Townhouse in Windham
Windham Mountain Village 2 bedroom townhouse
10–17 Apr
£128 per night
4.88 out of 5 average rating, 97 reviews
Guest favourite
Home in Windham
Private 5 acre Windham Mountain Ski Retreat
17–24 Nov
£547 per night
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Windham
EAT, DRINK, PLAY ... and Relax in Windham
10–17 MayIndividual Host,
£286 per night
4.94 out of 5 average rating, 36 reviews
Guest favourite
Cottage in Windham
Cozy Cottage Retreat Close to Main St/Windham Mtn
21–28 May
£222 per night
5.0 out of 5 average rating, 13 reviews
Guest favourite
Guest suite in Windham
Cozy 2 bedroom apartment with private entrance
27 Apr – 4 May
£124 per night
5.0 out of 5 average rating, 35 reviews

Quick stats about holiday rentals in Windham

Total rentals

170 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

5.6K reviews

Nightly prices starting at

£71 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Windham