Search Vacation Homes in Winhall

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7
In one month
Dec 19 - Dec 21
In two months
Jan 16 - Jan 18

Vacation Homes in Winhall

Outdoor spa tub
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft

Jamaica
9.6 out of 10, Exceptional, (21)
"House was perfect and just what we were looking for! Very clean, great hot tub, loved the fire pit!Cassie was incredibly helpful with local recommendations and going above and beyond!Highly recommend!"
United States
Neal T.
$601 nightly
The price is $679
Dec 3 - Dec 4
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Fire Pit & Game Loft
Outdoor spa tub
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!

Jamaica
9.8 out of 10, Exceptional, (27)
"EXCELLENT location managed by an amazing host who was very communicative and helpful!Hottub was perfect, plenty of sleeping and activities available at the house and in the immediate area (local food was AWESOME)."
United States
s w.
$608 nightly
The price is $687
Nov 24 - Nov 25
Total with taxes and fees
Stratton Mountain Home - Hot Tub, Sauna, Fire Pit, & MORE!
Outdoor spa tub
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
9.6 out of 10, Exceptional, (30)
"It was exactly what we wanted. Fireplace , hot tub, and ample sleeping arrangements "
United States
Craig F.
$576 nightly
The price is $646
Nov 23 - Nov 24
Total with taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Exterior
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Winhall
10.0 out of 10, Exceptional, (8)
"Great location, large space for family, good amenities, love the fireplace and coffee set up."
United States
Eitan S.
$992 nightly
The price is $1,121
Dec 9 - Dec 10
Total with taxes and fees
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym
Interior
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
$149 nightly
The price is $167
Nov 23 - Nov 24
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
Interior
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
9.8 out of 10, Exceptional, (28)
"Beautiful location and very cozy place to stay. Thank you!"
United States
Kristin G.
$199 nightly
The price is $223
Nov 23 - Nov 24
Total with taxes and fees
Peaceful Stay at Birds of a Feather Farm & Spa
Smart TV, fireplace, table tennis
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Dover
10.0 out of 10, Exceptional, (5)
"We enjoyed our stay."
United States
Anonymous traveler
$385 nightly
The price is $435
Nov 23 - Nov 24
Total with taxes and fees
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Fridge, microwave, oven, stovetop
The Carol - 10 minutes to Okemo & Newly Renovated

The Carol - 10 minutes to Okemo & Newly Renovated

Cavendish
10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
United States
Esther K.
$264 nightly
The price is $295
Nov 22 - Nov 23
Total with taxes and fees
The Carol - 10 minutes to Okemo & Newly Renovated
Interior
Charming Cavendish Guesthouse

Charming Cavendish Guesthouse

Cavendish
9.8 out of 10, Exceptional, (7)
"Just as described with Everything we needed. Very comfy and roomy. Loved the private feeling and backyard. Would highly recommend to anyone wanting to stay in this area of Vermont."
United States
deborah m.
$248 nightly
The price is $277
Nov 22 - Nov 23
Total with taxes and fees
Charming Cavendish Guesthouse
Fridge, microwave, oven, stovetop
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly
9.8 out of 10, Exceptional, (36)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
$462 nightly
The price is $517
Nov 22 - Nov 23
Total with taxes and fees
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Fridge, microwave, oven, stovetop
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

South Londonderry
9.6 out of 10, Exceptional, (4)
"Host was accommodating with responses."
United States
Michael S.
$367 nightly
The price is $415
Nov 23 - Nov 24
Total with taxes and fees
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming
Interior
The Dorothy-10 minutes from Okemo- freshly renovated

The Dorothy-10 minutes from Okemo- freshly renovated

Cavendish
9.6 out of 10, Exceptional, (4)
"We had an enjoyable stay! Our hosts were very communicative and thought of the details for our stay!"
United States
Maya T.
$261 nightly
The price is $292
Nov 24 - Nov 25
Total with taxes and fees
The Dorothy-10 minutes from Okemo- freshly renovated
Interior
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Stratton
7.8 out of 10, Good, (52)
"Location was great, pool, hot tubs and sauna were great"
United States
Lin M.
$249 nightly
The price is $282
Nov 25 - Nov 26
Total with taxes and fees
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Depot
9.6 out of 10, Exceptional, (16)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$311 nightly
The price is $348
Nov 23 - Nov 24
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
Smart TV, fireplace, video games, offices
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

Wilmington
10.0 out of 10, Exceptional, (17)
"Great place!"
United States
Jack & Heather G.
$580 nightly
The price is $620
Dec 9 - Dec 10
Total with taxes and fees
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Terrace/patio
Mountain Dream Escape

Mountain Dream Escape

2.0 star property
Sandgate
10.0 out of 10, Exceptional, (1)
"Beautiful location and home! The apartment was beautifully decorated and so cozy. The hot tub was a great place for stargazing! It was wonderful for our anniversary weekend but would also be great for a longer stay.Great communication with hosts and they were super helpful when we had a minor issue with check in."
United States
Morgan C.
$428 nightly
The price is $480
Dec 15 - Dec 16
Total with taxes and fees
Mountain Dream Escape
2 bedrooms, WiFi, bed sheets
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

2.0 star property
Londonderry
8.0 out of 10, Very Good, (1)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
$440 nightly
The price is $497
Dec 1 - Dec 2
Total with taxes and fees
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Fridge, microwave, oven, stovetop
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow
9.8 out of 10, Exceptional, (103)
"A lovely time enjoying the off-season in a ski town. "
United States
Ed C.
$405 nightly
The price is $439
Nov 24 - Nov 25
Total with taxes and fees
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views

shushan
9.6 out of 10, Exceptional, (20)
"Lovely home. Very pet friendly. "
United States
Kimberly D.
$339 nightly
The price is $376
Nov 22 - Nov 23
Total with taxes and fees
Cozy Rustic Cabin In The Hamlet Of Shushan NY. with incredible views
Interior
MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)

MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)

Mount Holly
9.8 out of 10, Exceptional, (20)
"Everything was as expected. Very clean, great location. Would stay again!"
United States
Jenna K.
$473 nightly
The price is $530
Dec 1 - Dec 2
Total with taxes and fees
MT Holly Ski/lake house hideaway(Avail. Daily, weekends & seasonally Dec-April)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winhall Hotel Reviews

Knotty Pine

Knotty Pine

10/10 Excellent
"We stayed in room 19. It was very clean and worth the money. "
Chris 2-night trip
Posted 2 days ago
Knotty Pine

Find out more about Winhall

Winhall Vacation Homes information

Number of reviews
349
Accommodation
874 Vacation Homes
Lowest Price
$167
Highest Price
$1,121

Explore a world of travel with Expedia