Vacation rentals with outdoor seating in Windham

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Windham

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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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!

Sep. 29 – Oct. 6

$965 CAD per night

Guest favourite

Home in Durham

4.96 out of 5 average rating, 101 reviews

Wow! Panoramic Mountain View, Minutes to Windham!

This pristinely-kept vacation home has endless mountain views on rolling country acres. Come and stay just to get away, enjoy both the sunrise and sunset views from the expansive deck. Curl up by the wood burning fireplace or the outdoor fire-pit, or take a sunset plunge in our backyard hottub and enjoy the picturesque views of Windham, NY from across the valley. A serene 8 mile drive will take you into the historic Town of Windham, NY to enjoy a day of skiing, site-seeing, hiking or dining

Aug. 12 – 19

$614 CAD per night

Guest favourite

Apartment 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.

Sep. 26 – Oct. 3

$152 CAD 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.

Apr. 3 – 10

$251 CAD 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.

Oct. 1 – 8

$220 CAD 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.

Jun. 28 – Jul. 5

$283 CAD per night

Guest favourite

Cabin in Chichester

4.99 out of 5 average rating, 514 reviews

Garden Cottage In The Catskills

This quaint, relaxing cottage sits among Flowering Gardens in spring & summer, incredible Fall Foliage in autumn, & a Wonderland in Winter. Enjoy a peaceful cozy & private space with nature at your doorstep, an outdoor fire pit, stargazing, & your own stone patio at the edge of the woods. We love to share our garden, come pick your own! We are in the heart of The Catskill Mountains, 2 miles from the vibrant town of Phoenicia, in the hamlet of Chichester near the Stony Clove Creek

Aug. 19 – 26

$190 CAD per night

Guest favourite

Apartment in Acra

4.95 out of 5 average rating, 323 reviews

Mountain TOP Studio - Five State, 100 mile view-

Come Relax among the tree tops and enjoy a 100 mile view! Glass doors and a private deck reveal a five state view that's absolutley breathtaking. Nestled in the Catskill mountains, a private studio awaits you. Located minutes from hiking, biking, and ski trails! Sleep with the window open and you will hear a natural waterfall coming from the mountains. You will find a private parking area, your own entry/ exit way and a full kitchen including breakfast items for you to enjoy!

Sep. 25 – Oct. 2

$243 CAD per night

Guest favourite

Tiny homes 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)

Jan. 10 – 17

$158 CAD per night

Guest favourite

Cottage in Gilboa

4.94 out of 5 average rating, 200 reviews

Home Alone Mountain Retreat

The cottage is beautifully located in the small vacation community on the hill with a stunning mountain view from the wrap-around deck. Nature and sport enthusiasts will love the area. Take on the early morning stroll in the woods, wander around the historic villages, take a swim in the pond, enjoy the country roads on the mountain bike, and visit neighboring Windham and Hunter Mountain Resort. The kitchen is equipped with cooking essentials such as pots, pans, and utensils.

Nov. 6 – 13

$226 CAD per night

Guest favourite

Apartment in Freehold

5.0 out of 5 average rating, 224 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!

Jul. 10 – 17

$263 CAD per night

Guest favourite

Condo in Hunter

4.98 out of 5 average rating, 536 reviews

Hunter Mtn Liftside Ski In/Out, Slopeside!

Fantastic location! Liftside! Beautifully renovated SLOPESIDE ski on/ski off condo . Spacious one bedroom condo with fully stocked kitchen, luxurious bathroom with jacuzzi tub, large bedroom with queen bed, and comfortable, cozy open concept living and dining room. Real wood burning fireplace. Private deck backs up to the ski slopes at Hunter Mountain! Seconds away from the Kaaterskill Flyer lift , main lodge, and bar. Avail for seasonal rental 11/15-4/15 $15000

Aug. 26 – Sep. 2

$194 CAD per night