Pet-friendly vacation rentals in Windsor County

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Windsor County pet-friendly home rentals

Pet-friendly house rentals

Superhost
Home in Ludlow
4.87 out of 5 average rating, 46 reviews

Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo

LaurelRating, 5 stars1 month ago
David’s place was amazing! It was excellent for our group, and he was very communicative. Thanks so much!
Guest favorite
The exterior of a charming farmhouse showcases a spacious porch with multiple windows. Brightly colored chairs, in blue and yellow, are positioned on a grassy area, inviting relaxation. The surrounding landscape includes lush greenery and an open field, enhancing the tranquil setting.
Home in Cavendish
4.94 out of 5 average rating, 81 reviews

Close to Okemo, 25 Acre Mountain Playground

MichaelRating, 5 stars3 months ago
A beautiful place with an incredible view of the mountains- cozy and warm and extra comfy beds! Sheryl’s kitchen had everything we needed. And close to okemo
Superhost
The exterior of a spacious red house is set against a snowy landscape. Surrounding trees are bare, and a gentle slope leads to the house, which has a garage and a simple roofline. Snow blankets the ground, creating a quiet and serene winter atmosphere.
Home in Killington
4.84 out of 5 average rating, 88 reviews

Killington Racquetball House

EmersynRating, 5 stars2 weeks ago
This was our second time staying at the racquetball house and it was just as incredible as the first. Lucked out with some great spring skiing on Friday, and checked into the Airbnb after. The house is very conveniently located to the mountain. We made full use of the court. Played racquetball, volleyball, dodgeball, kickball, pickleball, wall ball. Basically just spent all weekend playing games in the court and then relaxing in the hot tub to end the day. The living room / kitchen area is a great gathering layout. We will definitely be back.
Superhost
The exterior of the house showcases a grey wooden siding, complemented by a rustic wooden barn door. Colorful flower pots filled with blooming plants line the garden bed, enhancing the welcoming vibe of the entrance. Large windows allow natural light, providing connection to the outdoors.
Home in Bridgewater
4.76 out of 5 average rating, 123 reviews

The Buddah House

LindseyRating, 5 stars1 month ago
We loved staying at Gina’s place. We had everything we needed and our stay was comfortable.
Guest favorite
A picturesque view of the home's exterior is framed by vibrant autumn foliage. Flowering shrubs with clusters of pink and green blossoms surround the manicured lawn, creating a natural border that enhances the charm of the recently renovated house in the background.
Home in Woodstock
4.98 out of 5 average rating, 42 reviews

Please note: we are not accepting new reservations

AmyRating, 5 stars3 months ago
We had a wonderful stay at Christine's beautiful home in South Woodstock. There was a small hiccup with the entry code, but she was very responsive. The house is cozy, quiet, and very well stocked for a great stay. While some AirBnbs lack kitchen supplies, the house is well equipped to prepare food for a group. We very much enjoyed the gas fireplace and comfortable sitting areas. We hope to return sometime in the summer months. Thank you!
Superhost
The exterior of a charming mountain home is displayed, featuring a sloped roof partially covered in snow. Surrounded by wintery woods, the house has a dark exterior with a vertical design and a stone chimney. Sunlight creates a bright ambiance, enhancing the snowy landscape.
Home in Pittsfield
4.83 out of 5 average rating, 78 reviews

Green Mountain/Killington Getaway

ErnieRating, 5 stars1 month ago
Six of us stayed four nights in March at Paula’s place. Everything was great. Of the ones that stayed in the bunks all agreed we slept great. Usually bunks are uncomfortable but it was nice here. We aren’t small either. The house had everything we needed and was close enough to the mountain. We had two days of good snowboarding. The access road to the house isn’t great but we all made it fine with a civic, X3, and F150. We would all stay here again. Paula is a great host.
Guest favorite
Home in Londonderry
4.97 out of 5 average rating, 141 reviews

Wild Blossom Farmhouse - a lovely family getaway

courtneyRating, 5 stars1 month ago
Cozy and charming getaway. Beautifully furnished with wonderful and responsive hosts.
Superhost
An aerial view captures the single-family home surrounded by vibrant autumn foliage. The open yard features a circular outdoor seating area near a firepit, with various outbuildings dotting the landscape. Pine trees provide a natural border, enhancing the serene mountain setting.
Home in Bridgewater
4.85 out of 5 average rating, 124 reviews

Blueberry Hill Escape Pet Friendly HotTub Fire pit

NancyRating, 5 stars1 month ago
The house is very comfortable and the coffee bar was a very nice touch. We enjoyed the hot tub and walks down the street. There is little to no traffic on the connecting road and it was nice for winter walking. The area is charming with rolling hills and brightly colored barns and houses. It was great to be able to have our doggy with us too. It is close to Killington and Woodstock is a cute little town.

Pet-friendly home rentals with a pool

Top guest favorite
The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.
Home in Mendon
4.89 out of 5 average rating, 245 reviews

Ranch at Mendon Mt Orchards

StephanieRating, 5 stars1 week ago
Perfect location for skiing, and cosy home that we all enjoyed (including our pup). We appreciated the thoughtful touches provided by the host, and the apple orchard was a beautiful setting. Would definitely stay again!
Top guest favorite
A modern condo building is surrounded by a blanket of fresh snow, with tall trees standing nearby. The structure features a combination of flat and peaked roofs, multiple windows, and an inviting entrance pathway lined with snow.
Home in Killington
4.98 out of 5 average rating, 133 reviews

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace

JeffreyRating, 5 stars1 month ago
Dan and Holly are wonderful hosts. Excellent condo unit in a quiet, private location yet very close to great skiing, excellent restaurants, and live music. Condo was spacious, clean, and well kept. Dan and Holly obviously really care about their guests. Highly recommended.
Top guest favorite
Home in Rutland
5 out of 5 average rating, 10 reviews

Entire Home, Near Slopes, Hot Tub, EV Charger

MicahRating, 5 stars1 month ago
The stay was excellent. The home was beautifully renovated. The rooms were large and very comfortable. Location was perfect for the 8 of us for a ski weekend at Killington. Hope to be back.
Superhost
A single-story house is framed by tall trees, creating a natural setting. The exterior features a combination of stone and siding, with multiple windows allowing light into the interior. A gravel driveway leads up to the entrance, surrounded by a neatly maintained lawn.
Home in Rutland
4.88 out of 5 average rating, 8 reviews

Green Mountain Getaway

HoiRating, 5 stars1 month ago
Excellent place for our group. Definitely would recommend. 10 out of 10
Superhost
A spacious two-story building is surrounded by snow-covered ground, showcasing a distinctive triangular roof and wooden siding. Tall evergreen trees are visible in the background, contributing to a serene mountain setting. A ski on/ski off logo is present in the lower corner.
Townhouse in Killington
4.68 out of 5 average rating, 73 reviews

SKI ON/OFF Spruce Glen D | Sauna | Fireplace

MatthewRating, 5 stars3 months ago
My family (2 adults, 11 yo daughter, dog) enjoyed a 4-night stay at Ryan's place in Killington over Christmas. The home was as described and in good condition. Ryan was very communicative and responsive. We would stay there again. We had one night of moderate snow (4-5 inches) and the driveway was cleared promptly in the morning. The one bummer about our stay was that the trail next to the house - Great Eastern - was not open while we were there. The Killington lodges are just a few minutes away by car, so not a big deal, but we did not have a ski-in/ski-out experience. Of course, this was completely outside of Ryan's control, but it is something to check on before you go. The trail finally opened the morning we left..
Superhost
An open space features a cozy living area with a red sofa and a queen bed draped in a colorful blanket. A wooden dining table with seating for four accompanies a modern kitchen equipped with stainless steel appliances, enhancing the suite's inviting design.
Condo in Killington
4.89 out of 5 average rating, 245 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

IanRating, 5 stars3 months ago
The place was great, clean, nice bathrooms. The oven seemed like it wouldn't go up to temperature at one point so I messaged the host and they responded right away to get the maintenance folks over. But it turned out that it was just set to Celsius and I was able to look up how to change it online (Hold down the broil button!). There were PLENTY of towels/linens which was nice.
Guest favorite
A wood stove is positioned within a brick fireplace, showcasing a warm fire glimmering behind a glass front. The surrounding brick offers a rustic touch, while stockings hang above, adding a seasonal element to the cozy ambiance.
Home in Chittenden
4.91 out of 5 average rating, 89 reviews

Comfortable, relaxing large country home

EdwardRating, 5 stars1 month ago
Great spot for a week of skiing! Danielle was very helpful and communicative throughout
Guest favorite
The exterior of a multi-level townhouse is shown, featuring an inviting entrance with a peaked roof. A set of wooden stairs leads up to the doorway, flanked by a white railing. Surrounding foliage includes trees and colorful autumn leaves.
Condo in Killington
4.97 out of 5 average rating, 147 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

EileenRating, 5 stars1 month ago
Nice place for the 6 of us and dog for a long ski weekend in March. Condo was as described. The kitchen was very clean, nothing in fridge. New fridge and new oven. The bathrooms were very clean. The beds were comfortable. The upstairs space a bit tight for 4 adults, but we managed fine. Two of the twin beds are in an open loft area, which didn’t bother us as we were all going to bed at the same time and waking early to go skiing. Just mentioning this in case you were looking for a 3rd bedroom that was fully enclosed. The Spa and Cafe/ Wine Bar were a great addition to our ski weekend activities. The host was wonderful and very responsive. We highly recommend this condo.

Private, pet-friendly home rentals

Guest favorite
A charming two-story house is displayed with a colorful autumn tree in the foreground. The exterior features light-colored siding and a gabled roof. The front porch is accessible and surrounded by well-maintained shrubs, enhancing the home's inviting appearance against a clear sky.
Guest suite in Lebanon
4.92 out of 5 average rating, 109 reviews

Convenient and chic private suite with 2 bedrooms!

DianeRating, 5 stars2 weeks ago
Again, wonderful stay! Simple but has what one needs to be homey and comfortable. Quiet, clean, comfortable beds. New heat plate makes doing simple cooking easy. Jules is always very responsive and accommodating.
Superhost
A spacious living area is shown with a grey sectional sofa arranged around a central ottoman. A soft glow emanates from an indoor gas fireplace, while a colorful bear painting adorns the wall. Natural light filters through the windows, illuminating the neutral tones of the room.
Townhouse in Plymouth
4.97 out of 5 average rating, 30 reviews

Cozy Townhome in the heart of the mountains

MarinaRating, 5 stars6 months ago
We fully enjoyed staying at Daniellle's place. It is conveniently located within 15 minutes of Killington and within 30 minutes of Woodstock. the place is very clean and updated. The beds were very comfortable and we had everything we needed to cook our meals. I would stay at Danielle's place again.
Guest favorite
Barn in Woodstock
5 out of 5 average rating, 11 reviews

Green Mountain retreat: The Skyland Duplex

JoshRating, 5 stars6 months ago
This is the second time we stayed at Jeffrey's place. We love the location and Jeffrey makes it easy.
Top guest favorite
The exterior of a two-story cabin is framed by vibrant autumn foliage. A gravel driveway leads to the cabin, featuring a grey wood façade and a single window. Surrounding greenery enhances the secluded atmosphere, creating a peaceful setting amidst nature.
Cabin in Mount Holly
4.98 out of 5 average rating, 241 reviews

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi

LorenRating, 5 stars3 weeks ago
Beautiful cabin in a great location. We so enjoyed our stay. Their guidebook was well put together and have great suggestions of things to do the day we were iced out at the mountain.
Top guest favorite
The rustic cabin, surrounded by lush trees, features a porch with a picnic table. The wooden structure is designed with a gabled roof and large windows, providing a welcoming entrance. Flower boxes adorn the front, enhancing the natural setting.
Cabin in West Windsor
4.97 out of 5 average rating, 242 reviews

Sunset Cabin - your private romantic hideaway

SallyRating, 5 stars5 months ago
We *LOVED* our time in the Cabin in the Woods. Sondra and Daniel were very responsive in responding to questions about the property. The layout of the cabin was sensible and comfortable and the bed was very comfortable. We would love to go back! The cabin location is perfect and is sweet and romantic. Sondra and Daniel have thought through every detail. Thanks again for a splendid vacation spot!
Guest favorite
The exterior of a country cottage is shown, featuring a wooden porch with stacked logs and a white picket fence. Lush green trees surround the property, and a rustic barn structure is visible in the background, set against a cloudy sky.
Cottage in Londonderry
4.88 out of 5 average rating, 67 reviews

Vermont Country Cottage(Near Village w/Magic View)

TiffanyRating, 5 stars3 weeks ago
Such a cute little cottage. Close enough to town but far enough to feel secluded. My daughter loved the bunk beds and adored the loft so much especially since it had so many toys. Thanks again!
Guest favorite
A gravel pathway meanders through a wooded area, surrounded by trees showcasing vibrant autumn foliage in shades of yellow, orange, and red. Fallen leaves are scattered along the ground, creating a natural carpet that enhances the serene outdoor setting.
Cabin in Hartland
4.97 out of 5 average rating, 30 reviews

Private Log Cabin near Quechee

JudyRating, 5 stars2 weeks ago
We wanted to check out Halley’s log cabin as a possible place to bring our dog when we come to this area to visit our daughter and her family. The cabin itself is very pet-friendly with good-sized rooms, and the surroundings are great for a dog to explore. The cabin is on a quiet road, and when I walked each day there was very little traffic, so safe for walking a dog! We found that it was very peaceful for sleeping. When we had a couple questions, Halley was very quick to respond. As several others have mentioned, you are not far from Quechee and Woodstock and the major highways, so if you want privacy and convenience then this place fits the bill.
Top guest favorite
A well-maintained campsite with a picnic table shaded by a large umbrella. Surrounding the area are several blue camping chairs arranged for relaxation. A small flower garden is visible, bordered by a stone outline, with a tent pitched nearby under the trees.
Campsite in Shrewsbury
5 out of 5 average rating, 15 reviews

Private Campsite 37 Acres (Pet-Friendly!)

AnnRating, 5 stars6 months ago
This was a lovely 3 min hike-in hike-out very private excellent campsite. All the amenities Youn described matched and he is wonderfully responsive and generous to help carry our tent and things with his atv. He is an exceptional host :)

Destinations to explore