Pet-friendly vacation rentals in Winhall

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Winhall pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
A single-story home with blue siding is set on a grassy lawn. A patio area contains a table and chairs, shaded by an umbrella. Surrounding trees provide a natural backdrop, and a fire pit is located nearby, completing the outdoor space.
Home in Granville
4.85 out of 5 average rating, 187 reviews

Home by the Mettowee River- Simply the best!

LoganRating, 5 stars1 month ago
The place was great! Adorable home in a great location. Restaurant's, grocery stores, and activities were all within 5 min from the home, yet it was still on a nice quiet street. Had all the amenities listed which made it super easy to cook meals. Directions for check in and check out were very clear and easy to follow. Virginia and Dan were amazing hosts, easy to communicate with, hospitable, and very attentive. Definitely a place I would highly recommend!
Guest favorite
A scenic road stretches into the distance, bordered by trees displaying vibrant autumn colors. Green and orange foliage contrasts against the cloudy sky, while a white picket fence runs along one side of the road, enhancing the natural landscape.
Home in Shaftsbury
4.86 out of 5 average rating, 127 reviews

Quaint One-Story Vermont House with Mountain View

JacquesRating, 5 stars1 week ago
Great stay. Very quiet and peaceful. Place was immaculate on arrival.
Guest favorite
Home in Jamaica
5 out of 5 average rating, 13 reviews

Magic Cottage in Jamaica Vermont

SamRating, 5 stars1 month ago
Melanie’s place was terrific! It is a great comfortable place, plenty of size for the whole family. We cooked great family meals in the evening and enjoyed the board games in the house. Approximately equal distance to Stratton, Magic or Mt Snow- 25min
Superhost
A comfortable living area is highlighted by a gray sectional sofa and a wooden coffee table. A patterned area rug adorns the floor, while a tall bookshelf displays various items. Natural light enters through the window, complementing the warm color of the walls.
Home in North Adams
4.72 out of 5 average rating, 50 reviews

Large Charming Home close to MassMoca

CatalinaRating, 5 stars3 months ago
Had a lovely holiday week in Nancy’s home! We felt right at home. The home was cozy and beautifully sun lit in the mornings ! Nancy had decorated before leaving and it was adorable and sweet. The yard was amazing for my 2 large dogs - they ran around and found toys to play with. The area was walkable with sidewalks that were mostly cleared after the snow. Hilly for sure ! Good workout hehe Super close to MassMoCA and the center of North Adams. Walked a few times with the dogs. There’s a dog run near by as well. A short drive from Bennington, Pittsfield and a handful of ski resorts. We had a great stay. Friendly neighbors, communicative host and lovely surroundings :) would love to be back!
Guest favorite
A charming farmhouse sits in the lush green landscape, surrounded by trees and vibrant foliage. The exterior features a combination of white and gray siding, with a distinct brick chimney at the center. The well-maintained lawn invites relaxation and exploration.
Home in Jamaica
4.84 out of 5 average rating, 247 reviews

Historic 1832 Parker House ~ Sleeps 10, Pool Table

Cr7Rating, 5 stars1 month ago
Erin's home in Vermont was absolutely perfect! Even better than we anticipated. Lots of room, super cozy, exceptionally clean, and a hop, skip, and jump from Stratton Mountain Resort! The game room was a real bonus. There is a small grocery store within a block of the home where we found everything we needed. Erin was easily accessible by phone and text and she is a wonderful host. We highly recommend her home; we will definitely be booking again!
Superhost
A spacious two-story house is displayed surrounded by a lush green lawn, with a durable metal roof and a screened porch extending along the front. Tall trees provide shade, creating a serene outdoor atmosphere, while a gravel path leads to the entrance.
Home in Cavendish
4.83 out of 5 average rating, 151 reviews

Okemo-Ludlow, fireplace, hottub, sleeps 13

LilyRating, 5 stars1 month ago
My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.
Top guest favorite
A charming single-story home is presented with a welcoming porch adorned with lattice work. A well-kept lawn surrounds the house, complemented by decorative plants. A covered area provides shade, while a dog can be seen relaxing on the grass in front of the entrance.
Home in Poultney
4.92 out of 5 average rating, 119 reviews

Cozy Home in Poultney, Vermont.

AndrewRating, 5 stars2 weeks ago
Kimberley's place was the perfect weekend getaway, with plenty of space, a very responsive host, and exactly as described on the website. Had we not brought our own boardgames to play, she even has a nice collection to stay busy now matter what the weather is outside. Would love to stay there again next time I am planning a board gaming trip!
Top guest favorite
The exterior of the home is presented with a combination of wood shingles and green siding. A welcoming entrance is highlighted by a blue door and a spacious wooden deck leading up to the porch, surrounded by a natural landscape.
Home in Townshend
4.94 out of 5 average rating, 212 reviews

Comfy and Cozy House on 67 acres

AllanahRating, 5 stars2 months ago
Surrounding area was very peaceful and the wrap around porch was a great way to see the nature. We loved the wood burning stove. Eccentric details and the space felt lived in.

Pet-friendly home rentals with a pool

Guest favorite
The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars2 months ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Superhost
A spacious porch features wooden flooring and a ceiling with exposed beams. Two Adirondack chairs are positioned invitingly, perfect for enjoying the surrounding nature. Sunlight casts shadows on the porch, highlighting the log cabin's rustic charm and the lush greenery beyond.
Cabin in Wardsboro
4.92 out of 5 average rating, 201 reviews

Leonard’s Log - Private Hot Tub, Fire Pit, A/C

IsabelRating, 5 stars1 month ago
This was the second time I booked Erin’s place and my group and I loved it! The outdoor jacuzzi is a huge highlight. The house is spacious and very comfortable.
Guest favorite
A chalet-style building with a wooden exterior stands in a snowy landscape. Sunlight illuminates the sloped roof, and smoke is seen rising from the chimney. Snow-covered evergreen trees frame the structure, set against a backdrop of distant wooded hills.
Guesthouse in Granville
4.9 out of 5 average rating, 894 reviews

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 stars1 day ago
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.
Guest favorite
Barn in Newfane
4.97 out of 5 average rating, 150 reviews

Beautiful rustic woods and fields retreat.

AmberRating, 5 stars1 month ago
This was my third time staying on Rosalind's property, but my first time in the "retreat" unit. The space is better in person than in the photos! It's a spacious two level unit with a huge bedroom/loft type area, perfect for setting up your yoga mat! The high ceilings and large forest facing windows in the bedroom were a highlight for me. Rosalind has always been a very responsive, thoughtful, and flexible host. I can't wait to stay again!
Top guest favorite
A white cottage is set amidst trees with autumn leaves, featuring a double garage door and a side window. The surrounding yard is grassy and dotted with fallen leaves, while the façade showcases a simple design complemented by a clear blue sky.
Cottage in Newfane
4.99 out of 5 average rating, 227 reviews

Cozy Vermont Antique Sugar House with Fireplace

BarbaraRating, 5 stars3 weeks ago
Lenore’s Place made us feel right at home. The cozy fireplace setting is perfect for a cold day. Lenore even baked delicious fresh banana muffins and was so gracious. The sleeping arrangements were very comfortable. The decorating was very well done. This space provided a very tranquil one night stay for us.
Guest favorite
A wooden deck with two orange chairs overlooks a serene pond surrounded by vibrant autumn foliage. A small sandy area leads to a floating dock on the water, creating a peaceful spot for relaxation and enjoying nature.
Tiny home in Brattleboro
4.87 out of 5 average rating, 213 reviews

“Sugar Maple” Rustic Cabin Getaway with Fireplace

HannahRating, 5 stars3 weeks ago
We had a blast! We took our dog Anica with us and everywhere was so dog friendly. We loved the area, so peaceful and quiet! Would have liked a bit more privacy as far as the curtains go however I understand wanting to have natural sunlight peaking through. Overall such a great find and Sean was fantastic!
Guest favorite
A cozy bungalow is partially obscured by lush greenery, with a spacious patio featuring a dining table under a large umbrella. Sunlight filters through the trees, creating a relaxed outdoor space that invites leisurely activities.
Home in Williamstown
4.89 out of 5 average rating, 217 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars2 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.
Guest favorite
A charming home is nestled among tall trees, surrounded by lush greenery. Sunlight filters through the leaves, casting playful shadows on the soft moss-covered ground. The inviting exterior features a warm color palette and a well-maintained garden, enhancing the serene forest setting.
Chalet in Winhall
4.88 out of 5 average rating, 106 reviews

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton

BrandonRating, 5 stars1 month ago
Peaceful, Serene location just 10 minutes from Stratton. We enjoyed the use of the new hot tub, and roomy kitchen. This space is surrounded by nature with plenty of space for you and your group. Would definitely stay here again!

Private, pet-friendly home rentals

Top guest favorite
A play area is visible, featuring a large wooden playset with a slide, set against a green lawn. Lush trees and flowering shrubs create a natural backdrop, adding a sense of tranquility to the outdoor space.
Home in Cambridge
4.97 out of 5 average rating, 39 reviews

Country hideaway

GwenRating, 5 stars8 months ago
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!
Guest favorite
An outdoor deck features rustic wooden furniture, including a round table and accent chairs. A golden retriever is seen on the red-painted floor, surrounded by fallen leaves. The entrance of the A-frame home is visible, with a red door and large windows framed by trees.
Tiny home in Wardsboro
4.94 out of 5 average rating, 324 reviews

Little Red House Vermont

JorgeRating, 5 stars1 month ago
What an amazing place to visit Vermont. I had a great time at the little red house. The place is beautiful and quiet. It is a 12 min drive to Mount Snow. Joe has a bunch of classic DVDs and we enjoyed some of them during our stay. The place is very clean and there is warm water and WiFi.
Guest favorite
A welcoming porch features two wooden rocking chairs positioned on weathered gray flooring. A decorative wooden sign with a paw print and the words 'Welcome to the House' leans against the wall. A doorway leads into the home, with a doormat at the entrance.
Home in Clarendon
4.86 out of 5 average rating, 29 reviews

Mountain Cottage for ski weekend. Pet Friendly!

CraigRating, 5 stars1 month ago
The house was perfect and Nicole was a fantastic and responsive host
Superhost
A serene outdoor space is highlighted by a circle of teal chairs surrounding a firepit, nestled among vibrant autumn foliage. Tall trees with colorful leaves create a peaceful backdrop, framing the spacious yard that invites relaxation and connection with nature.
Apartment in Wilmington
4.65 out of 5 average rating, 62 reviews

2 br apartment 12 mins to Mount Snow Unit #2

BrittanyRating, 5 stars5 months ago
They were upfront about the noise, and it really wasn’t much of an issue at all. Certainly noise from others, but nothing for concern. Enjoyed our stay!
Superhost
A spacious covered deck provides comfortable seating with wicker furniture and decorative pillows. A wooden table is present in the background, alongside a BBQ grill. Lush greenery surrounds the deck, creating a tranquil outdoor escape.
Home in Manchester
4.86 out of 5 average rating, 35 reviews

Your VT Dream House: Fireplace, Pool, Dogs

AtulRating, 5 stars8 months ago
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.
Top guest favorite
An outdoor deck area is framed by a decorative arch adorned with plants. A dining table and chairs are positioned nearby, with a barbecue grill visible on the side. Lush greenery surrounds the space, creating a secluded atmosphere.
Cottage in Wells
4.94 out of 5 average rating, 33 reviews

Private cottage in the woods

SergeyRating, 5 stars2 months ago
We enjoyed our stay so much! The place was nice and clean and quiet, perfectly organised and thought through. Karen was a welcoming, friendly, and helpful host. I wish more AirBnBs were like this! Would be happy to return someday.
Guest favorite
The exterior of the house is depicted, showcasing a large snow accumulation surrounding the structure. The blue façade contrasts with the white snow, and the roof is covered with a thick layer of snow. Bright sunlight radiates from above, illuminating the winter scene.
Home in Dover
4.93 out of 5 average rating, 91 reviews

New Hot Tub! Gas Fireplace! 2 min to Mt Snow

Stacie LynnRating, 5 stars1 month ago
We loved staying in your home. It was close to Mount Snow where we went skiing and we especially loved the fireplace and hot tub. The kitchen was so big and had everything we needed. Thanks so much for leaving the binder of instructions because it is important for us to treat your home like our own home and we want to do things right. We will be back next year. Tom and Stacie
Superhost
The exterior of a contemporary A-frame house is set amidst a forest, featuring a new deck with outdoor space. A pathway made of stones leads to the entrance, while sunlight filters through the surrounding trees, casting soft light on the facade.
Home in Jamaica
4.75 out of 5 average rating, 57 reviews

Green Mountain A-Frame with HOT TUB near Stratton

AdrianRating, 5 stars1 month ago
Had an excellent time and the cabin is extremely convenient for any nearby skiing! The house was very well kept (plenty of firewood available, hot tub was clean and ready to go on check-in, grill was gassed up, etc.), and plenty of space for even a large group. Would definitely recommend.

Quick stats about vacation rentals that are pet-friendly in Winhall

  • Total rentals

    120 properties

  • Nightly prices starting at

    ﺩ.ﺇ404 before taxes and fees

  • Total number of reviews

    4K reviews

  • Family-friendly rentals

    100 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

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