Holiday rentals in Windham

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Top-rated holiday rentals in Windham

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Guest favourite

Cabin in Durham

4.99 out of 5 average rating, 120 reviews

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!

23–30 Oct

$897 SGD per night

Guest favourite

Home in Durham

4.95 out of 5 average rating, 20 reviews

Charming retreat near Windham NY

Welcome to the Durso House, our charming (and quirky) newly renovated home ten minutes from Windham, NY. If the outdoors are your thing, we are minutes from skiing, hiking, and all the activities that the "Gem of the Catskills" has to offer. If you're looking for a retreat in the country, away from the rigors of city life, then you are also invited to make our abode your cozy (and romantic) retreat. Conveniently located off Route 23, simply zip out the door and let the adventures begin (or not)!

8–15 Apr

$182 SGD per night

Guest favourite

Home in Prattsville

4.91 out of 5 average rating, 271 reviews

Yanity House

You will have access to the entire house fully furnished. Pet's are welcome just keep paws clean its a beige rug. We want everyone to be comfortable, so please let us know how and what you would like to see improved if you rent the unit. We will improve the unit as per guest suggestions. Currently we do not have cable but we do have a dvd and game system in the living room - All the bedrooms have TV's, dvd players or bring your streaming device There currently is no phone but cell service works

22–29 Sep

$134 SGD per night

Guest favourite

Flat in Windham

4.99 out of 5 average rating, 211 reviews

Main Street, The Heart of Windham

The perfect base to explore Windham & spend time in the Mountains! Just 0.7 mi. to Windham Mtn/9 mi. to Hunter. Located where Main St. begins, this immaculate 1 Bdrm has a queen bed, open concept EIK/LR, Full Bath & Balcony. Roll-away bed avail. Hiking/ski/snowboard/music/dining/exploring. Near Wedding Venues-Wylder Hotel, Hayfield & Windham Manor. Walkable to restaurants, movies, pubs, galleries & shops. Parking. WIFI. Smart TV/NO CABLE. Bring your Roku/Amazon/Netflex/Hulu codes. DVDs avail.

11–18 Aug

$131 SGD per night

Guest favourite

Townhouse in Windham

4.91 out of 5 average rating, 111 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

11–18 Apr

$230 SGD per night

Guest favourite

Cabin in Maplecrest

4.94 out of 5 average rating, 163 reviews

Fraxinus House - Ideal for Windham & Hunter

Scenic country cabin located between Hunter Mountain and Windham Mountain, in the charming hamlet of Maplecrest. Surrounded by trees and the wilderness, it creates an idyllic mountainside escape, private and secluded grounds with only night stars and the sounds of wildlife. The decor is a mix of modern, color, and comfort, with lots of natural wood details. Both ski mountains are only a short 10 mins drive away. This is a great place for a romantic getaway or an outdoor trip in the Catskills.

1–8 Jun

$227 SGD per night

Guest favourite

Cabin in Tannersville

4.99 out of 5 average rating, 145 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

20–27 Oct

$198 SGD per night

Guest favourite

Apartment in Windham

4.89 out of 5 average rating, 133 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

21–28 Aug

$125 SGD per night

Guest favourite

Apartment in Hunter

4.97 out of 5 average rating, 428 reviews

*Great Reviews* Hunter Mtn. Close/Cozy/Clean Condo

*Clean, cozy studio condo in the Village of Hunter featuring vintage decor. Short walk to the Ski Slopes, Snowtubing Park, Scenic Skyride, Dolan's Lake/Beach, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. A Murphy bed w/ full size comfy Casper Mattress, a sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, strong WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks

12–19 Jun

$102 SGD per night

Superhost

Apartment in Windham

4.84 out of 5 average rating, 112 reviews

Studio 3 BEDS-SLEEP 4

Light-filled studio in downtown Windham. Beautiful mountain views from your balcony; at night gaze at the moon & stars If you want solitude, this is the place to be! Daytime, take a walk down to the river & enjoy! Walking distance to restaurants & small grocery. Studio is big, with closet, full bathroom, well-stocked coffee area with microwave and refrigerator. Maximum 3 people; 1 double & 2 twins. Check-in: From 4PM off-street parking, Free Wifi /Basic Cable /Linens/Coffee

17–24 Sep

$216 SGD per night

Guest favourite

Tiny home in Lexington

4.95 out of 5 average rating, 302 reviews

Diamond Notch - Mini A-frame, Spectacular Views

The Diamond Notch is a site-specific, passive-house level insulated, off-grid mini A-frame - locally designed & built by the architects in co-operation with Lexington Arts + Science (LA+S). Requires a 5 minute hike in. Bring hiking boots. Micro spikes or snow shoes provided if needed. Yes, there is a cozy propane fireplace inside which provides plenty of heat for cold winter nights. We provide bedding, limited cooking utensils and a fire pit. (no T mobile cell coverage)

6–13 Oct

$140 SGD per night

Guest favourite

Flat in Freehold

5.0 out of 5 average rating, 225 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

7–14 Jun

$243 SGD per night