
Pet-friendly holiday rentals in Windham County
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Top-rated pet-friendly home rentals in Windham County
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Pet-friendly house rentals

The Sugar House
Nice place, probably better in summer than winter, simply due to more amenities (like screened porch) and better able to appreciate the location, but it was nice as a winter spot, too, to sit and read by the fire. Kitchen was well-equipped, and the place was very clean.

Pinecone Pond
My family and I just returned home from a wonderful ski vacation! The home was just as pictured and the surroundings were absolutely beautiful!The house was immaculate and the ambiance was warm and welcoming. We had a great time skiing at Mt.Snow (30 minutes),exploring Brattleboro (12 minutes),preparing meals together and just spending quality time with each other! On another note….. Cat and Ed were very responsive and were always available if we had any questions! My family and I are already looking forward to returning next year ! Thank you again for EVERYTHING! Carol and Gene

1850's VT Farmhouse on the River
We had a great experience with Erin and our stay! Erin was incredibly friendly and welcoming. She made sure to respond promptly to all our questions and requests, which really made us feel at home. Erin went above and beyond to accommodate our needs, ensuring we had everything we required for a comfortable stay. Her genuine care made our experience truly special. If you're looking for a wonderful host and a cozy place to stay, I highly recommend booking with Erin.

Frosted Willows
The place had great scenery and was comfortable. Weather was horrible throughout the weekend but we managed to have a great time in the home anyway. Chelsea was very responsive and helpful.

Hot Tub & Game Room - Ski Mt. Snow/Stratton
We stayed for a weekend at Kelley and Jason’s home in Vermont and everything went great. From check in, to the local recommendations, to the quiet setting, we enjoyed a great time away. Hot tub, game room and the large deck were great.

The Grafton Chateau
The Grafton house was perfect for our multi-family with the big space, bedrooms, and bathrooms. We loved the living room area where we could all sit together for family games. The property and house are beautiful and the perfect Vermont vibes. As a skiing family, we liked the location between our favorite ski resorts. Raphael was a wonderful host in providing instructions before our arrival and helpful advice. We really enjoyed our stay at the Gafton house.

Wild Blossom Farmhouse - a lovely family getaway
We had a wonderful weekend in Vermont! The Airbnb was beautiful, clean and in a great location!

June in Vermont! (Pet Friendly)
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.
Pet-friendly home rentals with a pool

Cabin | Chalet | Mt Snow | Hot Tub & Pool Access
The stay was exactly as described in the photos and listing. Brian provided everything I needed for a productive working vacation—high-speed internet, comfortable accommodations, and a peaceful environment to relax and recharge during downtime. Highly recommend!

Leonard’s Log - Private Hot Tub, Fire Pit, A/C
The cabin was lovely! We went for a little weekend getaway with some friends and it is a great space for such an occasion. There is a surprising amount of space in and around the house and we didn't even use the three season porch. The hosts were also very responsive and easy to communicate with. Definitely a cute little home away from home!

Family/Dog Friendly Mountain Home w/ Amenities
Jake's house was the perfect fit for our family. It was spacious allowing for us to spread out if we needed personal space but also perfectly suited for hanging out together in the family room and kitchen area. The bedrooms were large and there were many options to choose where to sleep. The house was very clean and beautiful overall. I had a few questions and Jake was quick to respond. I would highly recommend this place.

Mt Snow Chalet: Peaceful Escape w/Hot Tub
We loved the Snow Chalet!! Such beautiful surroundings and well appointed. The beds were super comfy and the black out shades were great for the kids. Location was great and close to the grocery stories. Wilmington is a sweet town too with lots of cool shops. The club house pool was warm and the pool was nice and toasty. An awesome trip!

Wander In | Close to Mount Snow & Stratton
This place was a dream for families. We traveled with 4 children and an infant. The house was roomy for the whole crew to hang out and eat together. We loved how clean and organized it was. We enjoyed hours at the pool, which was a huge hit with the littles. VRM was very helpful with any questions that came up. The location was great for skiing at Mt. Snow. We wish we had stayed one more night but our infant became very sick and had to head back a day early. To be honest, the place is more beautiful in person than in the pictures and we feel so lucky to have been able to stay there. Big plus to have laundry on site. Kitchen has everything you need to cook all your meals.

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
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!

The Vermont Barn (Mount Snow)
My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
Lovely house can’t wait to rebook for next snowboard trip!
Private, pet-friendly home rentals

Cottage
The cottage was absolutely amazing, we will definitely be back for another visit. Thank you Denis and Megan!

Snug Chalet - Wi-Fi + Close to Mount Snow
We loved our time in West Dover! The house is perfectly situated between West Dover and Wilmington! Our dogs loved the fenced in area and we loved the deck, the open concept space and the proximity to town. We will definitely be back!

The Carriage Barn
Place was clean, responded in a timely matter and looked exactly like the pictures! What a great experience ‼️

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike
A wonderfully quaint cabin that is a perfect landing spot for a weekend getaway with all modern amenities. Will definitely stay again when in the area.

Mountain Chalet mins from Mt Snow Skiing/hiking
We had a wonderful Easter weekend at Miguel & Rowena’s cabin in Dover! It was a very peaceful location to relax, have a fire on the porch, walk our dog, and spend time with family. The hosts were welcoming, helpful and the home was cozy! Additionally the check in/out was easy and it was clean.

Luxury “Tiny” House, Immersed In Nature (Timbery)
Very peaceful! The cabin is simple and has everything needed. A great place to come to clear your mind and reset in the midst of nature. The large soaking tub is a highlight. Bed was comfortable. The house is just far enough from the parking area that you don't really want to be making multiple trips back and forth. There is a sturdy cart available to haul your belongings, which made it easy. Bring good footwear like the host recommends, since the path and area around the house can become super muddy after rainfall. I'd be glad to come back here and fully recommend it!

Cozy Lakeside Tiny Home, Near Skiing
Thoroughly enjoyed staying at Christopher's Tiny House. it was just right for my minu retreat. The space was just as described and very calm and welcoming.

Beautiful Artsy Studio w/Fireplace - Pet-Friendly!
Julia met us at the arranged time give us a nice tour of the apartment and was available personally if we needed her or by text. We had a dog and there was adequate woods to walk her in near the house so that she could do her business. The place was quiet; had a big comfortable bed; kitchen facilities were perfect. Plus she gave us plenty of materials to make a fire in the fireplace. We will definitely come again.
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Pico Mountain Ski Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Dorset Field Club
- Baker Hill Golf Club
- Pineridge Cross Country Ski Area
- Clarksburg State Park
- Hildene, The Lincoln Family Home
- Ekwanok Country Club
- Brattleboro Ski Hill
- Hooper Golf Course
- Bretwood Golf Course
- Fox Run Golf Club