
Holiday rentals with outdoor seating in Windham
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Windham
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Designer Chalet with Sauna|Hot tub|Mountain View
Recognized as one of the Catskills’ most exclusive retreats, @lechaletcatskills is a modern-luxury escape where mountain serenity meets refined design. Set on 10 private acres near Hunter, Windham & Belleayre, this designer chalet invites you to unwind in style -think panoramic views, cedar sauna, hot tub under the stars & firepit for marshmallow nights. With a chef’s kitchen, curated interiors & nature all around, Le Chalet is the Catskills getaway your friends and family will be talking about.

Custom Catskills private retreat
This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm
Plan your all-seasons escape to this beautiful, luxury chalet with direct views of Windham Mt., just a 5 minute drive to the slopes. Situated at the end of a private road on 3+ acres, enjoy this mountain getaway's hot tub, oversized deck, pond, firepit, huge game room, and other modern amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

*Farmhouse Chic with Mountain and Lake Views*
Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Alpine Chalet on Spectacular Property
Inspired by their travels in the Swiss Alps, the hosts of the Mountaintop Chalet invite guests to their peaceful alpine guesthouse atop a mountain in the Northern Catskills. Nestled on a quiet, private road, the Mountaintop Chalet is just an 8 minutes drive to downtown Windham, NY, 10 minutes to Windham Mountain and 18 minutes to Hunter Mountain. This tranquil yet accessible setting makes it the perfect escape for couples, families and friends. Follow on Insta at mountaintop_chalet.

Casa Magda - Designer Home near Hiking + Swimming
Relax and recharge at Casa Magda—a design-inspiring home on 9 acres in Windham, NY—just 2.5 hrs north of NYC! For design lovers and nature seekers, this 1980s gem has been redesigned with modern flair and offers serene solitude. Relax by the hot tub, cozy up by the fireplace with a record and lounge around the campfire to view stellar constellations and the Milky Way. Explore nearby eateries and hikes. Ski the Windham slopes within a 7 min drive, or head to Hunter in 15 mins.

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!

Riverfront, Fireplace, 20 min to Hudson & Windham
Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Little Red Cabin Near Windham & Hunter w/ Hot Tub
Nestled in the woods, our 3 bedroom cabin offers the perfect escape from the hustle and bustle of everyday life. The cozy interior features a warm, inviting atmosphere with all the amenities you need for a comfortable stay. The spacious living room is the perfect place to unwind after a long day of exploring the great outdoors, complete with a cozy fireplace and outdoor hot tub that offer stunning views of the surrounding landscape. Follow us on IG @thelittleredcabinny

The Creekside Cabin - 5 mins to Windham Mt!
Nestled in the hills of Windham NY, the Creekside Cabin is a hidden gem just under 2.5 hours from NYC. Ideal for families and small groups of friends, this cozy cabin features three bedrooms, one bathroom, a comfortable living room overlooking a tranquil creek, and a fully equipped kitchen with a wood-burning fireplace. Whether you're looking for a weekend escape or a longer retreat, the Creekside Cabin offers a peaceful and relaxing stay in a beautiful natural setting.
Popular amenities for outdoor seating rentals in Windham
House rentals with outdoor seating

Modern Treehouse w/ Spa, Walk to Hunter Mtn.

Mountain house w/ Scandinavian BBQ hut Spa & more!

Hillside Views in Hudson Valley

Big Red Retreat 3 min to Windham Mountain & Golf!

Modern High-end 2BR2BATH in the woods of Catskills

Mountain and tree view cabin on 12 private acres

Private Waterfall Retreat on 10 acres

Lux Modern Cabin at Hunter Mountain
Apartment rentals with outdoor seating

Mountain View Apartment

Dog Friendly Uptown Apt Near Stockade + Backyard

Catskill Village House - Studio w/ Private Terrace

Burnt Knob Mountain Escape

Hudson River Beach House

Escape to a Sleek, Serene Studio on the Riverbank

Catskill Getaway, Ski Windham & Hunter Mountains

Chic Country Apt in Woodstock, NY
Apartment rentals with outdoor seating

Trailside At Hunter-Phase II-Hunter NY

Windham Condo

Hunter creekside condo with mtn. view

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub

Trailside Tranquility at Hunter Mountain

Hunter Mountain 2BR Condo - Steps to Mtn /Zip line

Perfect Catskills hiking getaway with fireplace

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £381 | £394 | £322 | £229 | £240 | £245 | £263 | £291 | £270 | £264 | £303 | £351 |
| Avg. temp | -4°C | -3°C | 2°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | -1°C |
Quick stats about holiday rentals with outdoor seating in Windham

Total holiday rentals
Explore 90 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at £106 per night before taxes and fees

Verified guest reviews
Over 4,070 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
90 of Windham holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Boston Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Rentals with a patio Windham
- Townhouse rentals Windham
- Apartment rentals Windham
- Family-friendly rentals Windham
- Rentals with pools Windham
- Rentals with a fireplace Windham
- Pet-friendly rentals Windham
- Fitness-friendly rentals Windham
- Cottage rentals Windham
- House rentals Windham
- Chalet rentals Windham
- Ski-in/ski-out rentals Windham
- Rentals with a hot tub Windham
- Rentals with a washing machine and dryer Windham
- Rentals with a firepit Windham
- Cabin rentals Windham
- Rentals with outdoor seating Greene County
- Rentals with outdoor seating New York
- Rentals with outdoor seating United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Resorts World Catskills
- Windham Mountain
- John Boyd Thacher State Park
- Howe Caverns
- Glimmerglass State Park
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Taconic State Park
- Plattekill Mountain
- Norman Rockwell Museum
- Hunter Mountain Resort
- Butternut Ski Area and Tubing Center
- Opus 40
- Albany Center Gallery
- Berkshire Botanical Garden
- Peebles Island State Park
- Pineridge Cross Country Ski Area
- Hancock Shaker Village
- Huck Finn’s Playland, Albany
- Naumkeag




