Pet-friendly holiday 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 favourite
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
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
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 favourite
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
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 favourite
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
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 favourite
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 favourite
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 favourite
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
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
Home in Landgrove
4.75 out of 5 average rating, 8 reviews

Private Tavern, Hot Tub, 8-Fireplaces, Spa Baths!

ShanleyRating, 5 stars3 months ago
we arrived late in the evening and was amazed at the size of the house. I was lost a few times as it has several staircases and several ways to get to the kitchen and pub area. The kitchen is well stocked, many pots and pans. All the tools you need. Also a very large stove and oven. Brand new fridge, a chefs work table and a separate dinning table for 8 or 10 people. Chefs delight. Plenty of dinnerware! The solarium was my favorite room morning and mid-day. Sunshine through the snow covered pines, very beautiful! Gas fireplace made it very cozy! In the evening we enjoyed the Pub area. Played ping pong, pool and watched some movies. Wood burning stove was very warming and pleasant to watch! Everyone slept well, and each bedroom had their own bathroom with a soaking tub. We really enjoyed Okemo, Magic mountain, the local farm stores and the Scottish pub MacLomains, friendly staff and great beers and food! Hope to return next year!
Superhost
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
Apartment 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 favourite
Home in Chittenden
4.91 out of 5 average rating, 89 reviews

Comfortable, relaxing large country home

EdwardRating, 5 stars2 months ago
Great spot for a week of skiing! Danielle was very helpful and communicative throughout

Private, pet-friendly home rentals

Guest favourite
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
Home in Ludlow
4.9 out of 5 average rating, 73 reviews

Updated 6BR Home 4 min to Okemo w fenced in yard!

TayRating, 5 stars1 month ago
Perfect to meet friends and ski! 3 minutes from Okema and short drive to Bromely. Responsive hosts. Cooked in useful kitchen. Would come back!
Superhost
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 favourite
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 favourite
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 favourite
Cabin in West Windsor
4.97 out of 5 average rating, 242 reviews

Sunset Cabin - your private romantic hideaway

SallyRating, 5 stars6 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 favourite
Cabin in Hartland
4.97 out of 5 average rating, 30 reviews

Private Log Cabin near Quechee

JudyRating, 5 stars3 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 favourite
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