Apartment holiday rentals in Winhall

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Top-rated apartment rentals in Winhall

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Top guest favourite
Flat in Bennington
4.93 out of 5 average rating, 202 reviews

Escape the City- Vermont Studio

Our studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Grn. Mtn. National Forest. It's on the second floor of our home (above the garage) through a private entrance with a personal deck and outdoor seating. Take an afternoon stroll to the Mile Around Woods, or day hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Top guest favourite
Flat in North Adams
4.97 out of 5 average rating, 643 reviews

Steps to MoCA Near SKI: 2bd + SAUNA!

Near ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and others. A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Top guest favourite
The entrance of the Bonnet St Barn features a deep red exterior with a sloping roof and an overhang. A small chair is positioned beside the door, framed by lush greenery and blooming flowers, enhancing the welcoming entryway.
Flat in Manchester
4.99 out of 5 average rating, 100 reviews

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!

Guest favourite
A comfortable white sofa with decorative pillows is positioned against a light wall. A small, light-colored side table holds a potted plant. Natural light streams in through a nearby window, illuminating the wooden floor and a blue woven rug beneath.
Flat in Dummerston
4.95 out of 5 average rating, 248 reviews

HeART Barn Retreat

Peaceful, romantic retreat in this stunningly large and magical barn. This 1850's historic remodeled barn apartment is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

Top guest favourite
The entrance features a white door with a decorative bell and festive wreath. Adjacent to the door is a potted plant and a small snowman figure. Two white chairs are positioned on the porch, with a light dusting of snow covering the ground.
Flat in Jamaica
4.85 out of 5 average rating, 213 reviews

The Getaway

Nestled in the woods but yet only; 10 min. (5.3 mls) to Stratton Mtn, 11 min. (7.6 mls) to Bromely Mtn, 26 min. (18.2 mls) to Magic Mtn, 33 min. (19.2 mls) to Mount Snow, 50 min. (38.2 mls) to Okemo and 68 min. (51.2 mls) to Killington. Also only minutes away from Southern Vermont golf resorts, Appalachian, Long and West River Trails, beautiful ponds rivers and falls, state parks, Manchester outlet shopping and the Equinox, fine dining and the most brilliant foliage in New England.

Top guest favourite
A spacious sleeping area is highlighted by large windows dressed in soft curtains, allowing natural light to fill the room. The bed features a checkered blanket with decorative pillows, paired with a simple side table and a small plant, enhancing the cozy ambiance.
Flat in Brattleboro
4.98 out of 5 average rating, 135 reviews

Bright and Modern Chestnut Street Apartment

Enjoy a unique stay at this central, beautifully-remodeled apartment in quaint Brattleboro, Vermont. The apartment is attached to the back of the charming 1914 home where I live, and has a private, separate entrance so guests can come or go as they please. This carefully-curated apartment includes tasteful decor, a well-appointed kitchenette, organic cotton sheets, and natural bath products. Just off Hwy 91, the apartment is located in the quiet, historic neighborhood of Esteyville.

Guest favourite
A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.
Flat in Bennington
4.95 out of 5 average rating, 176 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Guest favourite
An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.
Flat in Townshend
4.93 out of 5 average rating, 252 reviews

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. Our Observatory features a historic 8½" Cooke telescope for unforgettable stargazing. Centrally located near Stratton, Mount Snow, Magic, and Bromley. Sleeps 5; adjoining unit available.

Top guest favourite
The exterior of a two-story house is visible, featuring a sloped roof and white siding. Lush green bushes frame the front yard, where a small decorative archway and white picket fence add charm. Surrounding trees provide a natural backdrop for the property.
Flat in Manchester
4.99 out of 5 average rating, 295 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio.

Top guest favourite
Flat in Manchester
4.97 out of 5 average rating, 100 reviews

Comfort & Style for Winter and Spring Vacations

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, new carpeting, paint 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.

Guest favourite
The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.
Flat in Londonderry
4.96 out of 5 average rating, 596 reviews

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).

Top guest favourite
A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.
Flat in Andover
4.98 out of 5 average rating, 451 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Popular amenities for Winhall apartment rentals

Quick stats about flat rentals in Winhall

  • Total holiday rentals

    Explore 10 holiday rentals in Winhall

  • Nightly prices starting at

    Winhall holiday rentals start at $220 SGD per night before taxes and fees

  • Verified guest reviews

    Over 60 verified reviews to help you choose

  • Wifi availability

    10 of Winhall holiday rentals include wifi access

  • 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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