Pet-friendly vacation rentals in Pittsfield

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Pittsfield pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
Home in Granville
4.85 out of 5 average rating, 188 reviews

Home by the Mettowee River- Simply the best!

RichardRating, 5 stars1 week ago
This is my third time staying at Virginia’s house. She is very responsive, checking in via a message to see if everything is going well. It’s an easy walk to the shops and restaurants in the center of the village. I plan to be back again next year.
Guest favorite
Home in Bristol
4.88 out of 5 average rating, 155 reviews

Large New England Home w/ Gorgeous Mountain Views

ChristopherRating, 5 stars2 months ago
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.
Superhost
Home in Killington
4.76 out of 5 average rating, 54 reviews

Breakaway House "B" Side: Renovated Ski Home

MelanieRating, 5 stars1 week ago
Beautiful relaxing property. Owners very responsive and accommodating. Great for small kids and dogs. Nice big open common area for group-lounging.
Superhost
Home in Rutland
4.88 out of 5 average rating, 8 reviews

Green Mountain Getaway

HoiRating, 5 stars1 month ago
Excellent place for our group. Definitely would recommend. 10 out of 10
Guest favorite
Home in Goshen
4.84 out of 5 average rating, 285 reviews

Nature Lover's Paradise

RobertRating, 5 stars6 days ago
We always love staying here. It’s so peaceful and the sound of the brook is so relaxing! Philip responds quickly and is an excellent host!!
Top guest favorite
Home in Warren
5 out of 5 average rating, 14 reviews

LaFlame Chalet - 10 mins to Sugarbush

JohnRating, 5 stars4 weeks ago
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!
Top guest favorite
Home in Poultney
4.92 out of 5 average rating, 119 reviews

Cozy Home in Poultney, Vermont.

AndrewRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Brandon
4.93 out of 5 average rating, 128 reviews

Rand’s Retreat

AnneRating, 5 stars4 weeks ago
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.

Pet-friendly home rentals with a pool

Guest favorite
Yurt in Randolph
4.94 out of 5 average rating, 452 reviews

Upper Yurt Stay on VT Homestead

TeganRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Granville
4.96 out of 5 average rating, 141 reviews

Epic Views of the Green Mountains

StephenRating, 5 stars4 weeks ago
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!
Top guest favorite
Apartment in Barre
4.94 out of 5 average rating, 163 reviews

Relax in Recreation Paradise!

JenniferRating, 5 stars1 month ago
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!
Top guest favorite
Home in Mendon
4.89 out of 5 average rating, 245 reviews

Ranch at Mendon Mt Orchards

StephanieRating, 5 stars1 week ago
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!
Top guest favorite
Home in Killington
4.99 out of 5 average rating, 134 reviews

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

JennRating, 5 stars3 days ago
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.
Guest favorite
Guesthouse in Granville
4.9 out of 5 average rating, 894 reviews

Moon Valley Country Retreat no clean fee pets yes

AmberRating, 5 stars4 days ago
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.
Guest favorite
Condo in Killington
4.94 out of 5 average rating, 256 reviews

Wood-Burning Fireplace/Dog-Friendly/Spa Onsite/AC

DenaRating, 5 stars1 week ago
Wonderful! Five of us (two different families) stayed for a week of snowboarding. It was close to the mountain and had everything we needed. The condo was clean and just as described. Some might find it small, but it had everything we needed. The hosts were responsive and helpful. Highly recommend.
Superhost
Condo in Killington
4.89 out of 5 average rating, 245 reviews

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

IanRating, 5 stars3 months ago
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.

Private, pet-friendly home rentals

Guest favorite
Guest suite in West Lebanon
4.92 out of 5 average rating, 111 reviews

Convenient and chic private suite with 2 bedrooms!

JordanRating, 5 stars2 weeks ago
Second time staying here and it was a pleasure once again. Very clean, comfortable bed and the place is very charming. Responsive host as well. Don’t snooze on Sheryl’s diner for a good cheap breakfast.
Superhost
Home in Ludlow
4.86 out of 5 average rating, 7 reviews

Newly Renovated 5-BR Home 10-min to Okemo

MichaelRating, 5 stars2 months ago
Great location on the main road, minutes to everything. Massive space with a great set up.
Guest favorite
Home in Clarendon
4.86 out of 5 average rating, 29 reviews

Peaceful Vermont Mountain Cottage -Pet Friendly!

CraigRating, 5 stars1 month ago
The house was perfect and Nicole was a fantastic and responsive host
Guest favorite
Condo in Waitsfield
4.97 out of 5 average rating, 37 reviews

Centrally Located, Light-Filled Apartment

JuliaRating, 5 stars3 weeks ago
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!
Top guest favorite
Cottage in Wells
4.94 out of 5 average rating, 33 reviews

Private cottage in the woods

SergeyRating, 5 stars3 months ago
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.
Guest favorite
Cabin in Northfield
4.88 out of 5 average rating, 64 reviews

Hilltop Cabin on Barrows Road

DeborahRating, 5 stars3 months ago
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!
Guest favorite
Cabin in Hartland
4.97 out of 5 average rating, 31 reviews

Private Log Cabin near Quechee

JudyRating, 5 stars3 weeks ago
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.
Guest favorite
Cabin in Ferrisburgh
4.89 out of 5 average rating, 27 reviews

Beautiful Log Cabin with views near Lake

DenieceRating, 5 stars3 months ago
Exceeded our expectations. Kristine was super responsive and extremely helpful. The cabin is so spacious and peaceful. Easy drive from Burlington and other surrounding towns. Planning our next stay already!

Quick stats about vacation rentals that are pet-friendly in Pittsfield

  • Total rentals

    30 properties

  • Nightly prices starting at

    $120 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

Destinations to explore