
House vacation rentals in Winhall
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Top-rated house rentals in Winhall
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Lawrence Cottage
Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

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)

Summit View Ski and Golf Retreat w/hot tub & Sauna
Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

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.

Vermont Botanical Studio Apartment
This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

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

Clean, Captivating VT Farmhouse near Stratton!
Let us welcome you to our beautifully appointed, circa 1901 Vermont farmhouse resting on four acres of lush, rolling pastures--the quintessential Vermont experience! The house exudes warmth, coziness and tranquility with no detail left untouched. 4 BR 2 bath with huge family room. Minutes to 3 of the best ski-mountains on the east coast - Stratton, Bromley, Magic Mtn and close to Manchester shopping. A few miles from renowned Solo Farm & Table, HoneyPie and West River Farmer's market.

Yellow Sweetie at the Base of Stratton
Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Stay mins from Mt. Snow & Stratton w/ EV charger
Enjoy the ultimate ski getaway in this private home that sits on 1 acre of beautiful wooded land. Park your car in the detached garage (w/Tesla charger). The spacious house comfortably sleeps 8 guests and sits between Stratton Mountain and Mount Snow with hiking trails and lakes just minutes away. Sit outside on the deck to enjoy serene views, warm sunshine and sounds of nature. Leave your worries and just relax, BBQ and enjoy the fire pit for cozy evenings with friends & family.

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.

Killington Retreat | Deck-Fire Pit-Mountain Views!
Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Stunning mid-century house on 2.5 private acres
Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.
Popular amenities for Winhall house rentals
House rentals with a pool

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

Magical Farm Getaway - a must visit!

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

Adams Farm-"The Little Farmhouse"

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Idyllic Dorset Home: Serene Escape w/amazing views

Historic Home on 17 acres of land. Go escape!

Historic 1850’s Renovated Farmhouse w/ Pool!
Weekly house rentals

Bright & Vibrant Mountain Home

Highland Haus: stunning ski getaway with hot tub

Mountain House between Stratton, Bromley, Magic

Scandinavian Serenity Close to Okemo

Glorious Mountain View in Dorset

The Vermont Hideaway

Vermont Mirror House

Ski Lodge Hideaway: 5 minutes to Stratton Mountain
Private house rentals

Charming Vermont Retreat

Modern cabin close to all mountains

Modern, Serene Farmhouse Retreat

*New!* Luxurious Stratton Mountain Chalet.

Home in the Heart of Dorset Village

Cozy 3-BR Retreat Near Stratton & Manchester

FULLY renovated 1 bed/1 bath ski in-out condo!

Modern Luxury at White Pine Lodge
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R11,169 ZAR | R10,552 ZAR | R8,308 ZAR | R5,533 ZAR | R4,951 ZAR | R5,379 ZAR | R5,704 ZAR | R5,910 ZAR | R5,619 ZAR | R5,893 ZAR | R5,619 ZAR | R8,754 ZAR |
| 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 house rentals in Winhall

Total vacation rentals
Explore 140 vacation rentals in Winhall

Nightly prices starting at
Winhall vacation rentals start at R2,056 ZAR per night before taxes and fees

Verified guest reviews
Over 3,660 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
70 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!
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- Apartment rentals Winhall
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- Rentals with a fire pit Winhall
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- House rentals Bennington County
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Saratoga Spa State Park
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Hildene, The Lincoln Family Home
- Hooper Golf Course
- Lake George Expedition Park
- Peebles Island State Park
- Dorset Field Club
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- National Museum of Racing and Hall of Fame
- Northern Cross Vineyard




