Vacation rentals in Winhall

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Top-rated vacation rentals in Winhall

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Guest favorite

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!

Nov 5 – 12

G$21,367 GYD per night

Guest favorite

Cottage in Jamaica

4.82 out of 5 average rating, 464 reviews

Forest Cottage ~ 7min to Stratton, Private, Views

Authentic Vermont post & beam cottage with privacy. 3 miles to Stratton's Sun Bowl, a 7-minute drive. Nearby swimming hole at the brook on the property. Dogs welcome, $30 fee per dog. No cats due to allergies. Vinyl record player, VCR/DVD player, board games, Starlink Satellite Internet 20-100 mbps. Heat options: 2 gas wall furnaces & wood stove. Front porch, propane BBQ, fire pit, picnic table & spectacular views of Stratton Mountain. Back deck surrounded by woods with hammock, table & chairs.

May 8 – 15

G$22,944 GYD per night

Guest favorite

Home in Winhall

4.98 out of 5 average rating, 132 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

Jun 27 – Jul 4

G$70,303 GYD per night

Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 185 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.

Jul 11 – 18

G$30,567 GYD per night

Guest favorite

Apartment in Manchester

4.99 out of 5 average rating, 147 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.

G$14,594 GYD per night

Guest favorite

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.*

Jun 3 – 10

G$27,326 GYD per night

Guest favorite

Home in Winhall

4.9 out of 5 average rating, 184 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.

May 24 – 31

G$96,338 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 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.

Aug 31 – Sep 7

G$21,418 GYD 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!

Jan 10 – 17

G$141,232 GYD per night

Guest favorite

Cabin in Winhall

4.96 out of 5 average rating, 291 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

Apr 4 – 11

G$58,414 GYD per night

Guest favorite

Condo in Stratton

4.96 out of 5 average rating, 117 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.

May 30 – Jun 6

G$27,810 GYD per night

Guest favorite

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.

May 28 – Jun 4

G$64,655 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Winhall vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Winhall's top sights

Stratton Mountain Resort173 locals recommend

Mulligan's43 locals recommend

The Fire Tower Restaurant & Tavern37 locals recommend

Stratton Mountain Golf Course28 locals recommend

Red Fox42 locals recommend

Winhall Market38 locals recommend

Other great vacation rentals in Winhall

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 196 reviews

Cozy cottage loft and retreat

Apr 4 – 11

G$18,764 GYD per night

Guest favorite

Tiny home in Jamaica

4.85 out of 5 average rating, 214 reviews

Hot Tub Farmhouse - Buttercup Studio - Jamaica VT.

Oct 22 – 29

G$21,794 GYD per night

Guest favorite

Chalet in Winhall

4.96 out of 5 average rating, 27 reviews

Beautiful renovated chalet mn to Stratton

Oct 23 – 30

G$29,181 GYD per night

Guest favorite

Chalet in Winhall

4.98 out of 5 average rating, 53 reviews

Mountain view chalet with hot tub & fire pit!

Nov 7 – 14

G$123,171 GYD per night

Guest favorite

Chalet in Winhall

4.95 out of 5 average rating, 74 reviews

3 Bedroom Cabin Near Skiing, Restaurants, Shopping

Jun 26 – Jul 3

G$52,174 GYD per night

Guest favorite

Guest suite in Manchester

5.0 out of 5 average rating, 10 reviews

Adorable 1-BR suite close to three ski resorts!

Aug 10 – 17

G$26,976 GYD per night

Guest favorite

Cabin in Winhall

5.0 out of 5 average rating, 58 reviews

Log Cabin Escape Close to Skiing & Shops

Sep 12 – 19

G$113,632 GYD per night

Guest favorite

Apartment in Dorset

4.96 out of 5 average rating, 25 reviews

Newly Renovated Cottage

Jun 26 – Jul 3

G$23,919 GYD per night

Show all

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
270 properties are a good fit for families
Total number of reviews
7.5K reviews
Nightly prices starting at
G$20,849 GYD before taxes and fees

Frequently Asked Questions

Are there Winhall vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes with pools in Winhall, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Winhall have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Winhall. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in chalet rentals in Winhall?
Experience the best of Winhall with our chalet rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Winhall?
Winhall has more than 270 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do chalet rentals in Winhall have air conditioning?
Absolutely! We offer over 20 chalet rentals with air conditioning in Winhall. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Winhall?
Yes! Work meets play with ease at over 160 vacation rentals in Winhall featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do condo rentals in Winhall have free parking?
Absolutely! We offer over 30 condo rentals with free parking in Winhall. Enjoy a tailored experience with all the comforts you desire.
Do townhouse rentals in Winhall have a kitchen?
Absolutely! We offer over 20 townhouse rentals with a kitchen in Winhall. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cabin Rentals in Winhall?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 20 homes with a kitchen, over 10 homes with air conditioning, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Winhall?
Four-legged friends are welcome in Winhall. Choose from more than 120 vacation rentals for guests traveling with pets.

Vacation rentals in Winhall

Top-rated vacation rentals in Winhall

Vacation rentals for every style

Houses

Cabins

Chalets

Popular amenities for Winhall vacation rentals

Stay near Winhall's top sights

Other great vacation rentals in Winhall

Guesthouse in Putney

Tiny home in Jamaica

Chalet in Winhall

Chalet in Winhall

Chalet in Winhall

Guest suite in Manchester

Cabin in Winhall

Apartment in Dorset

Quick stats about vacation rentals in Winhall

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there Winhall vacation rentals on Airbnb with pools?

Do apartment rentals in Winhall have wifi?

How much does it cost to stay in chalet rentals in Winhall?

Are there family-friendly vacation rentals in Winhall?

Do chalet rentals in Winhall have air conditioning?

Are there vacation rentals with a dedicated workspace in Winhall?

Do condo rentals in Winhall have free parking?

Do townhouse rentals in Winhall have a kitchen?

What are the most popular amenities for Cabin Rentals in Winhall?

Are there pet-friendly vacation rentals in Winhall?

Destinations to explore