
Pet-friendly vacation rentals in Windsor County
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Top-rated pet-friendly home rentals in Windsor County
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Popular amenities for Windsor County pet-friendly home rentals
Pet-friendly house rentals

Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo
David’s place was amazing! It was excellent for our group, and he was very communicative. Thanks so much!

Close to Okemo, 25 Acre Mountain Playground
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

Killington Racquetball House
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.

The Buddah House
We loved staying at Gina’s place. We had everything we needed and our stay was comfortable.

Please note: we are not accepting new reservations
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!

Green Mountain/Killington Getaway
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.

Wild Blossom Farmhouse - a lovely family getaway
Cozy and charming getaway. Beautifully furnished with wonderful and responsive hosts.

Blueberry Hill Escape Pet Friendly HotTub Fire pit
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

Ranch at Mendon Mt Orchards
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!

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

Entire Home, Near Slopes, Hot Tub, EV Charger
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.

Green Mountain Getaway
Excellent place for our group. Definitely would recommend. 10 out of 10

SKI ON/OFF Spruce Glen D | Sauna | Fireplace
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..

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

Comfortable, relaxing large country home
Great spot for a week of skiing! Danielle was very helpful and communicative throughout

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

Convenient and chic private suite with 2 bedrooms!
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.

Cozy Townhome in the heart of the mountains
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.

Green Mountain retreat: The Skyland Duplex
This is the second time we stayed at Jeffrey's place. We love the location and Jeffrey makes it easy.

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

Sunset Cabin - your private romantic hideaway
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!

Vermont Country Cottage(Near Village w/Magic View)
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!

Private Log Cabin near Quechee
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.

Private Campsite 37 Acres (Pet-Friendly!)
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 :)
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- Okemo Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Pats Peak Ski Area
- Ragged Mountain Resort
- Monadnock State Park
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- Dorset Field Club
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- Ekwanok Country Club
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- Bretwood Golf Course
- Fox Run Golf Club
- Hooper Golf Course
- Whaleback Mountain
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- Lake Sunapee Country Club
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