
Apartment vacation rentals in Winhall
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Top-rated apartment rentals in Winhall
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Private Apt. on Farm, Hot Tub with views!
Relax in a spacious private apartment on our 38-acre hillside farm with sweeping Vermont views. Two queen bedrooms, a queen loft, full kitchen, and private deck with keypad entry. Enjoy gardens, orchard, heritage livestock, and a shared hot tub. Observatory features a historic 8½" Cooke telescope https://www.airbnb.com/experiences/6812114?s=67&unique_share_id=f9d4ebb7-396a-4f65-9ed0-f2b464a4359c Centrally located near Stratton, Mount Snow, Magic, and Bromley. Sleeps 5; adjoining unit available.

Green Mountains of Vermont/ 20 Min to Manchester
We welcome you to come experience Vt. We are a quiet, private, cozy, clean, stay in the country. Located equal distances to all surrounding towns and ski areas. Drive the Green Mountain National Forest road #10 to Peru, Landgrove & Weston. Hike on the Appalachian and Long trail. Fish, bike, forage, swim and spelunk (caving) Dine & shop, Manchester, East Dorset, Wallingford & Rutland. Walk around Danby. Take a scenic drive to Pawlet & Dorset. Ski, Killington, Pico, Okemo, Bromley, Stratton.

Bonnet St Barn
Keep it simple at the peaceful, cozy and centrally-located Bonnet St Barn. Conveniently located steps from Manchester’s landmark 'Northshire Bookstore', restaurants and delightful shopping. The apartment is on the main floor of the two-story barn and features a king-size bed, a smaller second bedroom with a twin bed, AC, high speed WiFi, TV and a full kitchen for relaxing mealtimes. Less than 30-minute drive to Bromley & Stratton ski areas. Enjoy the Green Mountains of southern Vermont!

Berkshire Mountain Top Chalet
Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

River View apartment
Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Peaceful Ludlow base for exploring Okemo valley
Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

Shakespeare’s Folly Side Farm and AirBnB.
Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly a dog, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

The MoCA-Cabana: 2 bd + Sauna
Welcome to the MoCA-Cabana, our newest listing at Chase Hill Estate—the historic home of the owners of the factory that became MASS MoCA. More than just a house, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Dog heavenly! Private, beautiful and relaxing.
Bright, secluded, second floor one room suite with private bathroom overlooking Mill River and across a covered bridge. No neighbors visible, but near town. Fly fish in the back yard, sit around the firepit, enjoy fall foliage, and hike and ski. Swinging bridge and Appalachia long trail very nearby. Close to three ski resorts: Killington, Okemo, and Pico. Dogs are welcome and loved, with plenty of room to run. Comfortable queen-sized bed and couch.

Comfort & Style for Vacations & Getaways Anytime
At $195.00/night, our art-filled gem is a renovated 2-b/r in-town apartment w/ fully equipped luxury kitchen & Vt. marble counters. We offer hardwood floors, carpeting, and AC. Complete w/ designer & heirloom furniture, antique oriental rugs & original paintings by local artists. We offer peace and privacy. Only six miles to skiing, hiking and walking distance to all Manchester pleasures.

Cute VT Bungalow With 180 Degree View of NH
Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Vermont Getaway Apartment
A 2 bedroom apartment attached to our home, close to Stratton, Bromley, Magic, Okemo & Mt Snow Skiing, hiking, fishing, golfing, tennis, outlet shopping and fine dining all close by. Manchester a short drive. Hot tub available from 8am-8pm. Level 2 EV charger available for a $10 cash fee (and give us advance notice if possible so we can open the garage for you).
Popular amenities for Winhall apartment rentals
Weekly apartment rentals

Suite Sunset 311 Rice Lane Bennington VT

Charming Art Filled Apartment

49 River Street

Law Office Apartment

Apartment at Five Ferns

House on the Town Green

Charming Suite

Farmhouse Apt : Walk to Williams : Near Mass Moca
Private apartment rentals

Lovely 2 Bedroom Apartment w/deck & pond view

Dog friendly, near Stratton, Magic & Bromley

Farm land view.

Newly Renovated Cottage

Bread and Butter Apartment

Modern Vermont Retreat w/ Chef’s Kitchen

Contemporary forest eco-retreat, mountain views

Manchester Cottage
Apartment rentals with a hot tub

Ski-in/out Jackson Gore Studio w/Kitchen

Apartment in the Woods

Stratton walk on/off, King beds, FP, hot tub, pool

Dover VT 2 Bdrm Condo - Great For Remote Work

Walk to main lift! The Handle Studio @ Mt. Snow!

Lovely Southern Vermont Getaway for 2.

Summit’s Stratton Sneak Away II

Walk to Ski Lifts & Village | Hot Tub & Sauna
Quick stats about apartment rentals in Winhall

Nightly prices starting at
Winhall vacation rentals start at G$33,469 GYD per night before taxes and fees

Verified guest reviews
Over 50 verified reviews to help you choose

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

4.9 Average rating
Winhall stays are highly rated by guests—averaging 4.9 out of 5!
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- Apartment rentals Bennington County
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Killington Resort
- Berkshire East Mountain Resort
- Stratton Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Saratoga Spa State Park
- Dartmouth College
- Bromley Mountain Ski Resort
- National Museum of Racing and Hall of Fame
- Mount Sunapee Resort
- Montshire Museum of Science
- Emerald Lake State Park
- Rensselaer Polytechnic Institute





