Windham vacation rentals

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Top-rated vacation rentals in Windham

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

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Guest favorite

Cabin in Durham

4.99 out of 5 average rating, 117 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!

Oct 8 – 15

G$138,931 GYD per night

Guest favorite

Home in Prattsville

4.91 out of 5 average rating, 270 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

Apr 26 – May 3

G$20,143 GYD per night

Superhost

Cabin in Maplecrest

4.95 out of 5 average rating, 171 reviews

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.

Aug 2 – 9

G$90,978 GYD per night

Guest favorite

Apartment in Windham

4.99 out of 5 average rating, 210 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.

Sep 12 – 19

G$20,245 GYD per night

Guest favorite

Townhouse in Windham

4.91 out of 5 average rating, 108 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.

Apr 29 – May 6

G$20,437 GYD per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 130 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.

Jul 29 – Aug 5

G$20,263 GYD per night

Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 426 reviews

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

May 27 – Jun 3

G$15,967 GYD per night

Superhost

Condo 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

Jun 30 – Jul 7

G$33,500 GYD per night

Superhost

Townhouse in Windham

4.82 out of 5 average rating, 177 reviews

Redwood Retreat in Windham - minutes to Mtn!

True mountain getaway, just 2.5 hours from NYC!! Modern and clean 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Complex amenities include outdoor pool (open from Memorial Day through Labor Day) 2 tennis courts and a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails. NOW OPEN FOR 2024/25 SKI SEASON!!

Jun 9 – 16

G$30,494 GYD per night

Guest favorite

Tiny home in Lexington

4.95 out of 5 average rating, 298 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)

Aug 13 – 20

G$21,460 GYD per night

Guest favorite

Apartment in Freehold

5.0 out of 5 average rating, 218 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!

Jun 5 – 12

G$37,690 GYD per night

Guest favorite

Home in Windham

4.93 out of 5 average rating, 165 reviews

Extreme leisure minutes from action and adventure

Relax and unwind in uniquely styled home on secluded 14-acre private property. Conveniently located to Windham mountain, vineyard, horseback riding and hiking trails The Bridge as we lovingly call our home, was designed to be a space where extreme leisure is met with adventure. Wake up early enough, you will see deer and wild turkey graze through the meadow. Stay awake late enough and gaze upon the endless stars. Now with hi-speed wifi!! Follow us @TheBridge_windhamNY

Aug 7 – 14

G$95,241 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windham vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Windham

Guest favorite

Home in Durham

4.96 out of 5 average rating, 100 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

Jun 13 – 20

G$85,524 GYD per night

Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 143 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Sep 19 – 26

G$30,978 GYD per night

Guest favorite

Cottage in Roxbury

4.98 out of 5 average rating, 476 reviews

The Little House

Nov 15 – 22

G$26,865 GYD per night

Guest favorite

Cabin in Jefferson

5.0 out of 5 average rating, 430 reviews

"Far from the Madding Crowd" Cozy Cabin Retreat

Jun 1 – 8

G$21,804 GYD per night

Guest favorite

Cottage in Gilboa

4.93 out of 5 average rating, 199 reviews

Home Alone Mountain Retreat

Nov 4 – 11

G$30,588 GYD per night

Guest favorite