
House vacation rentals in Winhall
Find and book unique houses on Airbnb
Quick stats about house rentals in Winhall

Total vacation rentals
Explore 140 vacation rentals in Winhall

Nightly prices starting at
Winhall vacation rentals start at G$27,194 GYD per night before taxes and fees

Verified guest reviews
Over 3,690 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
140 of Winhall vacation rentals include wi-fi 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!
Top-rated house rentals in Winhall
Guests agree: these houses are highly rated for location, cleanliness, and more.

Lovers Honey Pond Treehouse with hot tub & sauna
Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Spacious Loft with View
Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

The Mushroom House of Manchester Vermont
Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.

Modern Cabin with Hot Tub & EV Charging Station
Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

MOUNTAIN NEST, views, Manchester, hot tub,
Convenient to downtown Manchester's outlet stores and restaurants,golf (equinox golf course 3 miles away) hiking, kayaking and fishing (battenkill river)skiing-Stratton or Bromley, hot tub on full deck with close-up views of Mount Equinox, these mountain views will either make you weep or sing for joy, dines 8 easy, master on main (king bed). This home was intended to bring INSIDE the natural beauty you see OUTSIDE. Complete with vaulted living area and exposed timber beams throughout!

3BR 2BA Stratton Condo w/ Fireplace & Forest Views
Newley renovated 3 bed 2 full bath condo on Stratton, just minutes to Stratton's base lodge. Kitchen is well equipped for cooking. Private balcony with forest views. All new appliances. Wood burning fireplace & firewood included. All beds & baths are on 2nd floor up spiral staircase which may be difficult for elderly or young children. Stairs are required. Master bed has en suite full bath and smart tv. Free parking. Living room has an 86" smart TV. Poker set, & board games.

Shred Shack: A/C | Hot Tub | Sauna | EV charger
Escape to the Shred Shack by 42 North LP, your ultimate mountain escape in Vermont! The Shred Shack offers stunning mountain & valley views from its expansive great room. Relax & recharge by the grand fireplace, in the private indoor sauna, or the mountain-view hot tub. Entertain effortlessly in the open-concept kitchen, dining, and living area – perfect for memorable meals & gatherings. Kids will love the unique indoor swing! Your perfect blend of adventure and comfort awaits!

Charming Vermont Schoolhouse
Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Serene & Pristine Vermont Home
Perfect for a staycation, as a work-from-home alternative, or for family vacations. Situated on the edge of picturesque 120 acre New Spring Farm that borders the Green Mountain National Forest, is this up to date charming home awaiting your visit. With brilliant natural light and rolling pasture views, the quiet dead end dirt road provides privacy, while still being only a mile from J.J. Hapgood general store and centrally located to multiple towns and ski areas.

Modern 3-bedroom A-frame in Londonderry w/ Pond
This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

Cozy Modern Sugar House with spectacular views.
This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.
Popular amenities for Winhall house rentals
House rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

Luxury Stratton Village Condo | Walk to Lifts, Din

Magical Farm Getaway - a must visit!

VT retreat Heated pool-Hot Tub-Sauna-fire pit

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Idyllic Dorset Home: Serene Escape w/amazing views

Stratton ski/walk on/off, King beds, FP, Hot tub

Hollywood Bungalow in the Berkshires #C0191633410
Weekly house rentals

Entire Chalet in Winhall, Vermont

Luxury VT Retreat. Breathtaking Views & Sunsets

Highland Haus: stunning ski getaway with hot tub

Brewster's Hollow

Idlewoods

Little Pond Homestead 4 miles to Stratton!

The Nest at Bromley Knolls

Secluded Getaway: Skiing, Sauna, Firepit, ACs
Private house rentals

2-Bedroom Home, 7 Minutes From Stratton Mountain

4 Bed /3 Bath Mountain Chalet in Stratton, VT

Cozy Getaway! Great Location!

The MountainTop | Stratton & Mt Snow | Fire Pit

Bear Den: Hot Tub + Secluded | Sleeps 8 | Modern

Ski Lodge Hideaway: 5 minutes to Stratton Mountain

5BR near Stratton- Hot tub, sauna, fire pit, views

Pettengill Schoolhaus scenic 2 min to main village
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$144,129 GYD | G$148,104 GYD | G$101,664 GYD | G$67,567 GYD | G$60,455 GYD | G$65,684 GYD | G$69,659 GYD | G$72,169 GYD | G$68,613 GYD | G$79,491 GYD | G$74,261 GYD | G$125,511 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 |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Atlantic City Vacation rentals
- Providence Vacation rentals
- Newport Vacation rentals
- Rentals with a fire pit Winhall
- Rentals with an EV charger Winhall
- Apartment rentals Winhall
- Pet-friendly rentals Winhall
- Rentals with outdoor seating Winhall
- Rentals with pools Winhall
- Rentals with a washer and dryer Winhall
- Fitness-friendly rentals Winhall
- Rentals with a patio Winhall
- Chalet rentals Winhall
- Townhouse rentals Winhall
- Rentals with lake access Winhall
- Cabin rentals Winhall
- Condo rentals Winhall
- Family-friendly rentals Winhall
- Rentals with a sauna Winhall
- Ski-in/ski-out rentals Winhall
- Rentals with a fireplace Winhall
- Rentals with a hot tub Winhall
- House rentals Bennington County
- House rentals Vermont
- House rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- West Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Killington Resort
- Rensselaer Polytechnic Institute
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Mount Monadnock
- Montshire Museum of Science
- Mount Sunapee Resort
- Emerald Lake State Park
- National Museum of Racing and Hall of Fame
- Massachusetts Museum of Contemporary Art
- Trout Lake





