
Pet-friendly vacation rentals in Weston
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Top-rated pet-friendly home rentals in Weston
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Pet-friendly house rentals

Breakaway House "B" Side: Renovated Ski Home
Well located, close to the Killington ski area and nearby restaurants etc. Nicely kept. Place was very warm on the inside, even though temp was in the teens outside. Host was very responsive, flexible and informative. Even though the bunk bed in one of the rooms was a bit wobbly, all the other beds in other rooms were very comfortable. All in all, we had a great stay!

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!

Quaint One-Story Vermont House with Mountain View
Great stay. Very quiet and peaceful. Place was immaculate on arrival.

Large Charming Home close to MassMoca
Had a lovely holiday week in Nancy’s home! We felt right at home. The home was cozy and beautifully sun lit in the mornings ! Nancy had decorated before leaving and it was adorable and sweet. The yard was amazing for my 2 large dogs - they ran around and found toys to play with. The area was walkable with sidewalks that were mostly cleared after the snow. Hilly for sure ! Good workout hehe Super close to MassMoCA and the center of North Adams. Walked a few times with the dogs. There’s a dog run near by as well. A short drive from Bennington, Pittsfield and a handful of ski resorts. We had a great stay. Friendly neighbors, communicative host and lovely surroundings :) would love to be back!

Modern Spacious Home with Mountain Views
My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️

Cozy Home in Poultney, Vermont.
Kimberley's place was the perfect weekend getaway, with plenty of space, a very responsive host, and exactly as described on the website. Had we not brought our own boardgames to play, she even has a nice collection to stay busy now matter what the weather is outside. Would love to stay there again next time I am planning a board gaming trip!

Rand’s Retreat
We had a great stay! Loved playing board games in front of the fireplace. The house is minutes to Brandon (an adorable town) but still feels away from it all.

Historic Riverfront House: 5 Bedrooms 3.5 Baths
Absolutely wonderful house for our group ski trip to Killington! The house is well appointed with 5 bedrooms and the bonus loft space with 2 additional full beds. Our group was 4 couples and 2 single guys, so the space accommodated us very well and felt even more spacious than the photos. Eric and CJ were able to easily accommodate requests from us and were very helpful. We LOVED this house and plan to try to come back during warmer weather.
Pet-friendly home rentals with a pool

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

The 1770 House
Another great weekend at Ed’s! It was our group’s second time staying here, and we loved it just as much as the first, which is to say—a lot! Ed is very considerate and responsive, and there’s plenty to do for everyone. We are already looking forward to next year!

SugarBear Pool, Hot Tub, 2 En Suite BRs, FirePlace
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.

Moon Valley Country Retreat no clean fee pets yes
There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

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!

Hollywood Bungalow in the Berkshires #C0191633410
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

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.

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!
Private, pet-friendly home rentals

Cute Cool Cabin! Plymouth, Vermont.
Alecia and John were meticulous hosts from the well curated guide book to their responsiveness when we had questions. All made for a wonderful family fourth of july! We look forward to returning.

Little Red House Vermont
What an amazing place to visit Vermont. I had a great time at the little red house. The place is beautiful and quiet. It is a 12 min drive to Mount Snow. Joe has a bunch of classic DVDs and we enjoyed some of them during our stay. The place is very clean and there is warm water and WiFi.

2 Bedroom Cottage-Green Haven Resort-Lake George
Couldn’t recommend Green Haven anymore. Barbara and Gregory were fantastic hosts, were extremely hands on and accommodating to make it a perfect stay for my family and dog. Everything in the listing is described perfectly and the property and cabins are super clean. Location is fantastic as well, just a very short drive into Lake George village.

Little House with Lots to Offer
I stayed at the Tiny House with my significant other and our dog for a small, private getaway during our anniversary. It was a nice, cozy little home for us which we all enjoyed. It was also great to be right next to a grocery store and near downtown Keene for food and activities.

Powder Park Place: Lower Unit. Cozy 2BR/1BA. Ski.
great stay!

Private cottage in the woods
We enjoyed our stay so much! The place was nice and clean and quiet, perfectly organised and thought through. Karen was a welcoming, friendly, and helpful host. I wish more AirBnBs were like this! Would be happy to return someday.

Sowilo Pine House. All-inclusive food and drinks.
Great place for a getaway in the mountains!Hunor and his family are very kind and accommodating. The tiny home was so nice and cozy, the views were amazing, the food was delicious, and the service was 10/10. There’s so much to do in the area and there are also great amenities at Sowilo. I would come again.

April/May special So Vt Cabin Mt Tabor Treasure
Second time staying here to hike the area trails. The place was immaculate as was my first visit. The hosts are wonderful and helpful. They gave me check in flexibility that added a lot of time to my plans for the day that ended up being a big value. Highly recommend.
Quick stats about vacation rentals that are pet-friendly in Weston
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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