Vacation rentals in Winhall

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Top-rated vacation rentals in Winhall

Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

Oct. 4 – 11

$164 CAD per night
Guest favourite

Home in Winhall

4.88 out of 5 average rating, 137 reviews

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.

Jun. 27 – Jul. 4

$426 CAD per night
Guest favourite

Home in Winhall

4.98 out of 5 average rating, 125 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

Jul. 23 – 30

$640 CAD per night

Popular amenities for Winhall vacation rentals

Stay near Winhall's top sights

Stratton Mountain Resort173 locals recommend
Mulligan's43 locals recommend
Stratton Mountain Golf Course28 locals recommend
The Fire Tower Restaurant & Tavern37 locals recommend
Winhall Market38 locals recommend
Red Fox43 locals recommend

Other great vacation rentals in Winhall

Guest favourite

Cottage in Jamaica

4.82 out of 5 average rating, 461 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

May 8 – 15

$183 CAD per night
Superhost

Cabin in Wardsboro

4.8 out of 5 average rating, 201 reviews

Log Cabin Near Stratton/Mt Snow

May 11 – 18

$188 CAD per night
Guest favourite

Chalet in Winhall

4.96 out of 5 average rating, 26 reviews

Beautiful renovated chalet mn to Stratton

Jun. 11 – 18

$214 CAD per night
Guest favourite

Chalet in Winhall

4.98 out of 5 average rating, 53 reviews

Mountain view chalet with hot tub & fire pit!

Jan. 22 – 29

$1,412 CAD per night
Guest favourite

Condo in Stratton

4.91 out of 5 average rating, 44 reviews

Stratton Mountain vacation spot

Jun. 8 – 15

$174 CAD per night
Guest favourite

Cabin in Winhall

5.0 out of 5 average rating, 58 reviews

Log Cabin Escape Close to Skiing & Shops

May 5 – 12

$627 CAD per night
Guest favourite

Chalet in Winhall

4.96 out of 5 average rating, 53 reviews

Mountain-View Ski Retreat 10 Minutes from Stratton

Oct. 9 – 16

$1,058 CAD per night
Guest favourite

Cabin in Winhall

4.99 out of 5 average rating, 75 reviews

Modern Chalet 5 min to Skiing & Town With King Bed

Jul. 10 – 17

$804 CAD per night
Guest favourite

Cabin in Winhall

4.99 out of 5 average rating, 67 reviews

Modern town and country cabin near Manchester, VT

Sep. 26 – Oct. 3

$872 CAD per night
Superhost

Cabin in Winhall

4.89 out of 5 average rating, 61 reviews

Chic Cabin with Fireplace at Stratton Mountain

Jul. 6 – 13

$663 CAD per night
Guest favourite

Apartment in Dorset

4.96 out of 5 average rating, 23 reviews

Newly Renovated Cottage

Apr. 26 – May 3

$164 CAD per night
Guest favourite

Cabin in Winhall

5.0 out of 5 average rating, 35 reviews

Stylish Getaway w/ Hot Tub close to Stratton

Jun. 10 – 17

$1,042 CAD per night

Quick stats about vacation rentals in Winhall

Total rentals

320 properties

Rentals with a pool

50 properties have a pool

Pet-friendly rentals

120 properties allow pets

Family-friendly rentals

260 properties are a good fit for families

Total number of reviews

6.6K reviews

Nightly prices starting at

$149 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Winhall