
Vacation rentals with outdoor seating in Windham
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Top-rated outdoor seating rentals in Windham
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

Fat Cat Barn - Close Okemo & Magic, Vermont
Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Riverbed Treehouse @hot tub & a new sauna & views!
The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Beautiful Timber Frame Retreat
This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

New Cabin in Jamaica
Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

The Owl's Nest - secluded cabin with bikes
Cozy cabin nestled in the secluded woods along a rushing brook just outside Grafton village. You'll find it in the heart of southern Vermont's ski and hiking country just a short drive to Green Mountain NP. Designed to wrap your soul in flannel sheets, this tiny home has all the charm to allow you to live out your cabin-life fantasies hassle free. Perfect for lovers, bromances, gal pals, cuddle buddies, close friends, and just about any one else who wants to unwind, get close and personal.

Treehouse Haven in Putney-All Seasons
Peaceful, private & fully equipped four-season treehouse, surrounded by nature. ☽ Private & secluded ☽ Central to activities & necessities ☽ Firepit, pellet stove, deck, grill & fully stocked kitchen ☽ Scrupulously clean, unscented products ☽ Clean composting outhouse ☽ Tea & local coffee ☽ Hot outdoor shower-Closed Nov-April ☽ 45min to ski resorts ☽ Swimming holes & hikes ☽ WiFi & electricity Retreat from the business of life; romance, with the family, or even a remote work sanctuary.

Magic Creek
Come enjoy our brand new hot tub! Magic Creek is quintessential Vermont- an antique made modern. The cozy living room with fireplace is an ideal spot to gather at the end of your day. The house has 3 bedrooms and a play room that doubles as a guest room. The house is bordered by a creek with peaceful water falls. Centrally located in the heart of ski country, minutes to Magic Mountain, 20 minutes to Bromley, and 30 to Stratton or Mt Snow, and 40 minutes to Okemo. Come and enjoy it all.

Apple Blossom Cottage: A Tiny House
The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. I am as close or as far away as you would like me to be with my house right next door.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Cabin-7 min to Ski Stratton-Woodstove-Views-Dog OK
Authentic post & beam cabin surrounded by forest. Private location off a quiet road, 3 miles to Stratton Sun Bowl (a 7-minute drive). Swimming hole at babbling brook on property, fire pit, hammock on porch, propane BBQ, picnic table, forest views. TV with VCR & videos, turntable & records, games, Satellite Internet & WiFi 20-100 mbps. Staircase to loft, gas heat, wood stove, pellet stove. Full kitchen. Easy to use, odorless composting toilet. Dog friendly.

The Architect's Cabin, on 10 Secluded Acres
Nestled on a rise in a woodland clearing is this intriguing cubist design reminiscent of Post and Beam ambiance. Stone and wood materials from the property have been assimilated into intriguing modern design features throughout. Walls of windows share the tranquil and private outdoor setting with the indoor livings areas. We only accept Instant Bookings, which require a verified account and positive host reviews. There is no Air Conditioning.
Popular amenities for Windham outdoor seating rentals
House rentals with outdoor seating

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Modern 3-bedroom A-frame in Londonderry w/ Pond

Lovely Brick Schoolhouse

Cozy Home in Village of Grafton

Contemporary Ascutney Cabin near Ski Areas

Killington Retreat | Deck-Fire Pit-Mountain Views!

Birdie's Nest Guesthouse

Cozy Train Depot in Putney Vermont
Apartment rentals with outdoor seating

HeART Barn Retreat

Contemporary forest eco-retreat, mountain views

Cozy Poultney Village Apartment

Minimal organic hideaway inspired by nature

Cooper's Place

Steps to MoCA Near SKI: 2bd + SAUNA!

Bright and Modern Chestnut Street Apartment

The Getaway
Condo rentals with outdoor seating

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Winter Dream! The Handle Lodge at Snowtree Condos

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Great 2 bedroom condo at Stratton Mountain

Serene Top Floor Condo (resort style amenities)

3 Story Condo - 5 Minutes to Mount Snow!

Okemo Ski-in/Ski-out, Steps to lift Condo

Hotel Chic - Home Comfort -Ski Easy.
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$61,709 GYD | G$59,199 GYD | G$55,643 GYD | G$40,791 GYD | G$40,163 GYD | G$37,235 GYD | G$57,525 GYD | G$39,326 GYD | G$39,117 GYD | G$52,296 GYD | G$47,066 GYD | G$60,663 GYD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about vacation rentals with outdoor seating in Windham

Total vacation rentals
Explore 20 vacation rentals in Windham

Nightly prices starting at
Windham vacation rentals start at G$20,918 GYD per night before taxes and fees

Verified guest reviews
Over 1,150 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
20 of Windham vacation rentals include wi-fi 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!
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- Rentals with outdoor seating Windham County
- Rentals with outdoor seating Vermont
- Rentals with outdoor seating United States
- Okemo Mountain Resort
- Stratton Mountain
- Monadnock State Park
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Mount Sugarloaf State Reservation
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Dorset Field Club
- Hooper Golf Course
- Whaleback Mountain
- Northern Cross Vineyard
- The Shattuck Golf Club
- Fox Run Golf Club
- Willard Mountain
- Autumn Mountain Winery
- Ekwanok Country Club




