
Pet-friendly holiday rentals in Winhall
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Winhall

Total holiday rentals
Explore 100 holiday rentals in Winhall

Nightly prices starting at
Winhall holiday rentals start at $166 SGD per night before taxes and fees

Verified guest reviews
Over 3,920 verified reviews to help you choose

Family-friendly holiday rentals
90 properties offer extra space & child-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
100 of Winhall holiday rentals include wifi 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!
Top-rated pet-friendly home rentals in Winhall
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants
WalkabilityOutdoor spacesWifi
4.95 out of 5 average rating, 270 reviews
Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!
Outdoor spacesWalkabilityAir conditioning
4.95 out of 5 average rating, 323 reviews
Beautiful Bromley/Manchester VT Retreat w/hot tub
"Manchester Moose!" Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains! YouTube video link @GreenMountainStay
Outdoor spacesWalkabilityHeating
4.9 out of 5 average rating, 183 reviews
Chic Cabin with Fireplace at Stratton Mountain
Originally built as a corn crib in the 1800s, this 2 bedroom, two bath cabin has been lovingly maintained and features many original details from wide pine floors to a brick fireplace. This beautiful post and beam cabin is nestled in the Green Mountains of Central Vermont with convenient access to some of the best skiing, hiking, & sightseeing: 10 min to Stratton Mountain and Bromley, 15 min to Manchester, 20 min to Magic Mountain, 30 min to Mount Snow, 40 min to Okemo, and 1 hour to Killington
Outdoor spacesPetsAccess
4.85 out of 5 average rating, 114 reviews
Log Cabin King Beds AC Near Hike Bike Swim Golf!
Kick back and relax in this calm, stylish, newly built log cabin which was finished in early 2022. Fully equipped with stainless steel appliances, soapstone counters, central a/c, all new furniture, mattresses and bedding. First floor master bedroom leads into a large, covered, screened in porch, which is perfect for your early morning coffee or evening cocktails. Starlink high speed Wi-Fi and a smart tv in the living room and bedroom. 7 Minutes from Stratton Mtn, 15 from Mt Snow. Nearby lakes!
Outdoor spacesPetsHeating
5.0 out of 5 average rating, 203 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.
PetsWalkabilityNearby
4.85 out of 5 average rating, 205 reviews
10 min from Stratton! Log Cabin w/ Beautiful Views
Spectacular views of Stratton Mountain! This cozy log cabin is set on 10 acres of land offering a quiet year round Vermont getaway. The home offers 3 bedrooms (all with mountain views), 2 baths and comfortably sleeps 7. Located 10-15 minutes from skiing (Stratton, Bromley and Magic), 25 minutes from shopping and dining in Manchester, and ½ mile from Gale Meadows Pond for hiking and water activities in the summer. If you’re looking for the ultimate Vermont experience, you’ve found your spot!
WalkabilityOutdoor spacesSkiing
4.95 out of 5 average rating, 128 reviews
Ski and Play in Manchester Center!
Fully renovated 2000 sf 5 bedroom/2 bathroom house in the heart of Manchester Center, VT! 6 miles to Bromley, 15 miles to Stratton, 6 miles to the Vermont Summer Festival horse show, and less than a mile to all of the shops and restaurants Manchester Center has to offer! You cannot beat this location no matter the season! The house is set back off the road and surrounded by woodlands so even with all of these amenities at your fingertips, you feel like you're far off the beaten path!
WalkabilityPetsSkiing
4.95 out of 5 average rating, 136 reviews
Shred Shack: A/C | Hot Tub | Sauna | EV charger
Escape to the Shred Shack by 42 North LP, your ultimate mountain escape in Vermont! The Shred Shack offers stunning mountain & valley views from its expansive great room. Relax & recharge by the grand fireplace, in the private indoor sauna, or the mountain-view hot tub. Entertain effortlessly in the open-concept kitchen, dining, and living area – perfect for memorable meals & gatherings. Kids will love the unique indoor swing! Your perfect blend of adventure and comfort awaits!
Outdoor spacesPetsGrill
4.95 out of 5 average rating, 114 reviews
Modern 3-bedroom A-frame in Londonderry w/ Pond
This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min). STR License 26-23-185
Outdoor spacesPetsCleanliness
4.99 out of 5 average rating, 153 reviews
Designer Chalet w/ Mountain Views close to it all
Private 3-bedroom, 2-bath chalet on 2.5 peaceful acres with beautiful mountain views. Comfortably sleeping 6 guests, it’s the perfect Vermont escape for ski weekends, foliage trips, outdoor adventure, or simply relaxing with family and friends. Enjoy nearby hiking, biking, swimming, waterfalls, golf, and scenic drives. Close to Jamaica State Park, Bondville, Stratton, and Mount Snow, with Manchester’s shopping and dining an easy day trip away.
PetsOutdoor spacesLaundry
4.98 out of 5 average rating, 112 reviews
Dog Friendly A-Frame Retreat near Hiking, Dining
Escape to The Vermont A-Frame, our dog-friendly retreat on the edge of Green Mountain National Forest! This cozy 1965 cabin comfortably sleeps 4 and is perfect for skiers, hikers, or those seeking relaxation. Features a stone fireplace, dedicated workspace with fast WiFi, and a fire pit. Your ideal base for exploring Southern Vermont's natural beauty and charming towns. Find us @thevermontaframe!
Outdoor spacesPetsFamily
4.96 out of 5 average rating, 391 reviewsPopular amenities for Winhall pet-friendly home rentals
Pet-friendly house rentals

The Vermont Farmhouse|Hiking|Dog Trails|Village
Outdoor spacesPetsLaundry
5.0 out of 5 average rating, 138 reviews
The Equinox Cottage
WalkabilityOutdoor spacesCleanliness
4.78 out of 5 average rating, 251 reviews
MOUNTAIN NEST, views, Manchester, hot tub,
PetsOutdoor spacesComfort
4.97 out of 5 average rating, 284 reviews
Warm Brook Farm | Farmhouse & Gardens | Hot Tub
PetsOutdoor spacesTV
5.0 out of 5 average rating, 140 reviews
Cozy private cabin near Okemo! Large Hot tub!
Outdoor spacesPetsQuiet
4.83 out of 5 average rating, 107 reviews
Picture Postcard Mansion in Manchester Village
Outdoor spacesPetsDecor
4.88 out of 5 average rating, 138 reviews
The Grafton Chateau
WalkabilityPetsCleanliness
4.95 out of 5 average rating, 142 reviews
Charming Chester Farmhouse Near VT Slopes
PetsWalkabilityDecor
4.85 out of 5 average rating, 108 reviewsPet-friendly home rentals with a pool

4BR Ski Chalet | Hot Tub | Mins to Stratton, VT
Outdoor spacesPetsQuiet
4.89 out of 5 average rating, 135 reviews
Mt Snow Chalet: Peaceful Escape w/Hot Tub
Outdoor spacesPetsIndoor spaces
5.0 out of 5 average rating, 131 reviews
Log Cabin Near Stratton/Mt Snow
PetsOutdoor spacesHeating
4.79 out of 5 average rating, 279 reviews
Moon Valley Country Retreat no clean fee pets yes
Outdoor spacesPetsBiking
4.91 out of 5 average rating, 1025 reviews
Historic Farm Stay | Heated Pool + Hot Tub
PetsWalkabilityHospitality
4.98 out of 5 average rating, 214 reviews
Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
WalkabilityPetsWifi
4.9 out of 5 average rating, 250 reviews
Family-friendly 4BR | Pools Hot Tub | Near Mt Snow
WalkabilityOutdoor spacesGrill
4.89 out of 5 average rating, 183 reviews
Hollywood Bungalow in the Berkshires #C0191633410
Outdoor spacesWalkabilityLayout
4.9 out of 5 average rating, 241 reviewsPrivate, pet-friendly home rentals

Pond Cottage
Outdoor spacesPetsFamily
4.97 out of 5 average rating, 189 reviews
The Birchwood Cabin - Stunning Mountain Views
PetsOutdoor spacesParks
4.99 out of 5 average rating, 162 reviews
Luxe HotTub, Sauna, Fall Leaves, Stratton /Mt Snow
WalkabilityOutdoor spacesHot tub
4.96 out of 5 average rating, 174 reviews
Bread and Butter Apartment
PetsDecorQuiet
4.99 out of 5 average rating, 104 reviews
East Cabin
PetsOutdoor spacesPool
4.98 out of 5 average rating, 179 reviews
Fall Escape - Winhall - Fire-pit, Hot Tub
PetsOutdoor spacesKitchen
4.97 out of 5 average rating, 33 reviews
Mountain House between Stratton, Bromley, Magic
WalkabilityOutdoor spacesAccess
4.97 out of 5 average rating, 31 reviews
Vermont cottage with water and mountain views
PetsOutdoor spacesAccess
4.99 out of 5 average rating, 68 reviewsWhen is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $729 SGD | $767 SGD | $524 SGD | $389 SGD | $383 SGD | $396 SGD | $390 SGD | $396 SGD | $351 SGD | $396 SGD | $369 SGD | $612 SGD |
| 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 |
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- Pet-friendly rentals Bennington County
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- Pet-friendly rentals United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Dartmouth College
- West Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Killington Resort
- Rensselaer Polytechnic Institute
- Mount Monadnock
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- Saratoga Spa State Park
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Montshire Museum of Science
- Mount Greylock
- Trout Lake





