Holiday houses in Winhall

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Top-rated holiday rentals in Winhall

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Guest favourite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

5–12 Nov

$200 NZD per night

Guest favourite

Home in Winhall

4.98 out of 5 average rating, 137 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

28 Aug – 4 Sep

$851 NZD per night

Guest favourite

Cabin in Jamaica

4.99 out of 5 average rating, 187 reviews

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.

14–21 Aug

$286 NZD per night

Guest favourite

Chalet in Winhall

5.0 out of 5 average rating, 15 reviews

Summer Get-A-Way! Hiking/Fishing/Biking/Swimming

Enjoy our centrally located chalet, perfect for Vermont enthusiasts! Located in Winhall, we are only a short drive to all your summer fun! Enjoy all the activates like golf, hiking, fishing, biking, and shopping. Stratton, Bromley, Magic, Mount Snow, Okemo and Manchester Center are all within 25 miles! Our home has all of the classic chalet charm while providing you with modern amenities and comforts. Discover our family-friendly retreat while enjoying all the best Vermont has to offer!

5–12 Nov

$626 NZD per night

Guest favourite

Apartment in Manchester

4.99 out of 5 average rating, 150 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, but you can enjoy the outside seating set in front of the house.

12–19 May

$177 NZD per night

Guest favourite

Condo in Stratton

4.94 out of 5 average rating, 138 reviews

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

17–24 Sep

$303 NZD per night

Guest favourite

Home in Winhall

4.9 out of 5 average rating, 185 reviews

A+ Stratton shuttle, Hot Tub, Sauna, 2 masters

GREAT WINTER 2 FAMILY SHARE - 5 STAR HOME! 4 BD 3.5 BA with 2 MASTER SUITES SPA AMENITIES FREE TO USE. PREVIOUS GUEST'S REVIEW IS WRONG REGARDING A USAGE FEE. HOT TUB, SAUNA, 2 FIREPLACES, BBQ GRILL, OUTDOOR FIRE PIT, HEATED BEDS AND FLOORS, PIMA COTTON LINENS, GOOSE DOWN DUVET, COTTON TOWELS, COFFEE STATION, SNACK STATION, FIREWOOD PROVIDED. JUST BRING CLOTHES AND FOOD. SMART HOME WITH HOME THEATER , GAME LOFT WITH DUELING XBOX's, HULU LIVE, NETFLIX, PANDORA AND PRIME.

17–24 May

$768 NZD per night

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 496 reviews

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. We are as close or as far away as you would like us to be with our house right next door.

21–28 Aug

$224 NZD per night

Superhost

Home in Winhall

4.94 out of 5 average rating, 109 reviews

Beautiful Stratton-Manchester VT Retreat w/hot tub

Stratton VT Slopeside Ski Home with incredible summit views, Minutes from Manchester, Beautiful newly remodeled VT vacation getaway nestled in the Green Mountains. 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!

13–20 Mar

$1,129 NZD per night

Guest favourite

Cabin in Winhall

4.96 out of 5 average rating, 293 reviews

A-Frame Mountain Retreat near Manchester

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 6 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

11–18 Jan

$692 NZD per night

Guest favourite

Condo in Stratton

4.96 out of 5 average rating, 118 reviews

Cozy condo within walking distance to the slopes.

Cozy condo within walking distance of the slopes and restaurants and shops at Stratton Mountain Village. After a day on the slopes relax in the hot tub or take a dip in the heated pool or maybe enjoy some time in the sauna. Then enjoy sitting in front of the gas fireplace and maybe watch a movie. TV is a smart TV, basic cable is included - personal password needed for Netflix, Hulu, etc.

25 Jun – 2 Jul

$286 NZD per night

Guest favourite

Home in Winhall

4.99 out of 5 average rating, 349 reviews

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.

13–20 Jul

$613 NZD per night