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

Home by the Mettowee River- Simply the best!
The place was great! Adorable home in a great location. Restaurant's, grocery stores, and activities were all within 5 min from the home, yet it was still on a nice quiet street. Had all the amenities listed which made it super easy to cook meals. Directions for check in and check out were very clear and easy to follow. Virginia and Dan were amazing hosts, easy to communicate with, hospitable, and very attentive. Definitely a place I would highly recommend!

Large New England Home w/ Gorgeous Mountain Views
This is a great house to stay in. There's a lot of space, places to sleep, sit and relax, eat, watch tv, play games, work, read, cook. Plenty of hot water.. Very private, although in a neighborhood. Nice back yard area when not covered in snow, looking up at the mountains behind. Sheri is top notch. Easy to reach, super friendly and helpful, easy going. We came at the tail end of a snow storm, but the driveway was cleared enough to get our car in and then Sheri worked with us to make sure everything was cleared before we had to go out the next day. Easy walk into the cute town of Bristol. Handful of nice shops (books, games, art, crafts, gifts, toys) and restaurants: Wokky's--ok Chinese/great staff; Minifactory--out of sight coffee/biscuits/sandwiches/fresh ingredients/lot of gluten free; Cubber's--locals' joint/excellent pizza/sandwiches; Farmhouse Chocolates--superb fresh organic truffles, bars, caramels/chocolatier is wonderful. Easy drive to Mad River Glen, Sugarbush for skiing.

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!

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

Nature Lover's Paradise
Had a fantastic time. Went backcountry skiing before work and then worked from his place with multiple people doing zoom calls without issues. Perfect place for us

LaFlame Chalet - 10 mins to Sugarbush
We had a great stay at this cozy Airbnb. Looks exactly like the pictures and is a perfect size for group of friends or family. We brought a dog and had no issues at all. The hosts were very kind and even helped us with some car troubles after an unexpected snow storm. Would recommend and overall great stay!

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!
Pet-friendly home rentals with a pool

Upper Yurt Stay on VT Homestead
I needed a little break from my every day Vermont life. This was the perfect spot to get away from everything, but still not be far from home. I would definitely go back! Thank you so much!

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!

Epic Views of the Green Mountains
Great place to take your family if you like to escape from humanity! Very remote setting and plenty of places to hike. The house is as described and the kitchen if fully stocked to make full dinners. My daughters, our German Shepard and I had a wonderful time. Suggestions - bring groceries as Granville is in the middle of nowhere. Closest store is in Rochester, 12 miles South. William was very commun icative and the value for the money was phenominal. Hope I can return next year!

Relax in Recreation Paradise!
Chad was an incredible host! He was extremely accommodating with any requests we had. The views from his place are breath-taking! We enjoyed snowshoeing from the backyard onto trails in the woods. I fell in love with his cat who visited daily! He kept the driveway plowed and salted in a timely fashion. We enjoyed our stay and would highly recommend his place!

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.

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.

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

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.

Hubbard Park guest suite
This was my second time staying here, and this time I stayed with my family in the bigger apartment, which was perfect for a family of four! The kids loved the huge bathtub and bunk beds!

Cozy cottage in peaceful location
We had such a fun trip! Nikki’s cottage was absolutely gorgeous, nestled in the countryside. Would absolutely stay here again!

Charming getaway tucked away in the Green Mtns
We appreciated how pet friendly this place was! Fenced in yard. Blankets to cover the furniture to allow dogs on them. Close enough to many different ski mountains. Perfect to come home to the wood stove and hot tub.

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

Centrally Located, Light-Filled Apartment
We were due to arrive on the day there was an unexpected snowstorm. Dan and Emily were super responsive and offered a generous and very helpful solution with planning travel and our stay. The space is great, lots of character went into the build and new, clean furnishings were a nice touch- especially in a pet friendly setting. Plenty of hot water, heat. Ideal for singles or couples who are looking to explore all that the area has to offer- centrally located and a quick, easy entry/ exit. All that is needed is there and none of what isn’t- efficient use of space. Very welcoming hosts, would stay here again next time we visit!

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.

Hilltop Cabin on Barrows Road
Thank you Carol for a wonderful stay at your home in Northfield Vermont. The home is beautifully maintained, comfortable and perfectly located for exploring the area, hiking and skiing. We especially enjoyed the well equipped kitchen and the beautiful property. The home is extremely well furnished and cozy, welcoming and relaxing. We would definitely recommend your home for anyone looking for a great stay in Vermont! I received a bonus service-Carol helped me remove all the snow from my car! What a great host!
Quick stats about vacation rentals that are pet-friendly in Pittsfield
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ441 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
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- Magic Mountain Ski Resort
- Cochran's Ski Area
- Baker Hill Golf Club
- Fort Ticonderoga
- Dartmouth Skiway
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- Adirondack Extreme Adventure Course
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- Hildene, The Lincoln Family Home
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- Killington Adventure Center
- Whaleback Mountain
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- Vermont National Country Club