
Pet-friendly vacation 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

Mountain House between Stratton, Bromley, Magic
This place is a gem! Large space but felt intimate and cozy. The fireplaces are great, the deck looked inviting but we had so much snow, we spent most of our time on the slopes. Amazing art work throughout, well stocked kitchen, and lots of light! Great space.

Magic Cottage in Jamaica Vermont
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

Frosted Willows
I had a wonderful stay while visiting Brattleboro for work. The house is just lovely and extremely comfortable. The kitchen had everything that we needed. I’m hoping to stay again in the future when working in the area.

Hot Tub & Game Room - Ski Mt. Snow/Stratton
We truly enjoyed staying here!! The hosts were amazing! They gave us plenty of local recommendations that made our stay so enjoyable. The home was wonderful. Plenty of this to do if you don’t want to leave. Game room was a great bonus!! We can’t wait to return!

Magic Creek
Cute Vermont farmhouse that had everything that you needed. We enjoyed Cooking inn and hanging out in the living with the fireplace. The hot tub was so much fun after a cold day on the mountains. There is a cute little coffee shop and super market only 10 minutes away.

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

Large Riverfront Home | Minutes to Stratton!
This was the perfect winter ski / snowboard getaway for our group of 16. We had 3 families and the room to bathroom / bed ratio in this property were perfect. There was plenty of private space in the bedrooms to allow for some peaceful away time and there was also ample shared space so we could enjoy being together. The house and property are extremely well taken care of and the host was very proactive with information and other helpful information about the location and surrounding area. Very close and easy to access Stratton Mountain! We had 7 inches of fresh snow during our trip and the driveway was plowed by 8AM - in time to make it to the mountain for the first lifts. Will definitely book again!

Brand new, 5 BR, next to Hermitage Club&Hermt Inn
We loved this house! And plan to come back again soon! Beautiful home with great amenities. Host was very responsive. We had a great visit!
Pet-friendly home rentals with a pool

Spring Hiking Pet Retreat I Game RM l ChimneyHill
Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!

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
This place is simply beautiful. Both the surroundings and the house. The beds had tons of pillows and the linens were high quality soft cotton. There was plenty of room for our group with 3 levels of home to hold us all. The kitchen was well appointed and beautifully designed. The backyard was so beautiful, we took our family photos there. The deck was a great place to hang out under the string lights around the fire pit, while keeping an eye on the kids in the living room through the big windows. We even saw a BEAR cruising by! The clubhouse, the tennis courts, the fishing pond, we did it all and it was absolutely magical. We will definitely be back!

Beautiful rustic woods and fields retreat.
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!

Chimney Hill Home w/ New Hot Tub & Amenity Center!
Awesome property! Stayed here for a ski trip with friends, we had a great time and the house was a great size for all of us! Hot tub works great and the indoor fireplace was fun to use as well. Would absolutely stay again. Super polite and responsive hosts.

Cozy Vermont Antique Sugar House with Fireplace
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.

“Sugar Maple” Rustic Cabin Getaway with Fireplace
Great quiet getaway for April VT weather

Stunning Family Cabin HotTub-Pool Arcade
We had a wonderful week once again at this beautiful, cozy cabin. It is always spotlessly clean and comfortable. Adam and Filipa are exceptional hosts - very kind and responsive. The location is perfect - easy to get into town to enjoy restaurants and to ski at Mt. Snow and even though we got a lot of snow and ice the driveway was plowed and sanded to make it safe for travel. I highly recommend this home for your trip to Southern Vermont. I can't wait to return!
Private, pet-friendly home rentals

Gorgeous Mt. Snow 3 bedroom chalet
Great place, nice and clean ,close to Mt Snow. Definitely a place I would stay again.

Walk to Village/Lake Whitingham
Nice stay in a comfortable apartment. Friendly hosts in a quiet neighborhood. Close to town and local attractions.

Stratton Views from the Hot Tub or Fire Pit!
Our stay at Forty Two North was great. It was very cozy and we felt right at home. The house was clean and accurately depicted. The hosts were prompt with response time. Our family skied at Stratton, it was close and easy to get to. We would definitely come back again.

Cozy mountain getaway between Mt. Snow&Stratton
Even better than the pictures. It was a great place for a ski trip. I enjoyed walking around the house and exploring the property. For the price you can’t beat it. I would definitely recommend staying here if you are looking for a place.

Rock River Retreat: VT Oasis Pet Friendly
Truly a magical place… the views are amazing. We actually frolicked in the river a bit even though it’s only April and there was small amount of snow on the ground… it was surprisingly refreshing for a feet dip… as far as the unit there was so much charm and care put into this place… we had a snack and beverage awaiting us and Carmella the cat had a snack and toy with a little pillow bed by the window and food dishes ready to use. These extra little touches are special ❤️ The inside is super cute and charming, I loved the bath tub…. I stayed 2 nights and took 3 baths 😂 after our 5 hr drive my daughter needed to use facilities but it took her a good 10 minutes because she loved every detail of the space. I hope to return in summer! Book this space if interested, I promise you will not be disappointed!

A-Frame Mountain Retreat near Manchester
I’ve had my eye on this place for a few years so I was very excited to stay here on a quick weekend trip! It’s very cozy, spacious and beautifully decorated. The four of us had a lot of room to relax and have our own spaces (two couples). The beds were comfortable and so was the couch. It’s also much closer to the town than I thought, making it easy to grab dinner or supplies. We were pleasantly surprised the spot we wanted to try for dinner was right down the road (Pearl’s Place was great!). We hope to be back in the fall sometime!

The Woodland A-Frame
A nice little spot for a weekend getaway in the woods. The fire pit outside was great and the view out the back windows was serene. We didn’t use the fireplace as it wasn’t cold enough. Anyways, the kitchen was well equipped with everything (just no microwave) and there was even a coffee grinder which came in handy. Would recommend!

Private 1st Floor Apartment/ Secluded Paradise
My stay at paradise Island was great and exactly what I needed for a couple weeks while I was working on a project ,I was able to relax ,rest, and enjoy a nice peaceful area and set my mind at ease ,met such wonderful hosts and very welcoming ,I appreciate the hospitality and what a beautiful place thank you again .
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- Okemo Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Saratoga Race Course
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Bousquet Mountain Ski Area
- Bretwood Golf Course
- Hooper Golf Course
- Baker Hill Golf Club
- Mount Sunapee Resort
- Hancock Shaker Village
- Clarksburg State Park
- Willard Mountain
- National Museum of Racing and Hall of Fame
- Hildene, The Lincoln Family Home
- Peebles Island State Park
- Ekwanok Country Club
- Northern Cross Vineyard
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