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

The Waffles House-cozy 4br w/hot tub, central loc
Very cute spot it's everything you need for a nice weekend. Love that it is dog friendly. The hot tub was perfect for the snowy weekend. Anne communicated really well. There were blankets for snuggling. We skied at Jiminy Peak, about 25 minutes away. This was conveniently located and close to restaurants and amenities.

Riverside Chalet near Mt. Snow & Stratton resorts
My family really enjoyed the stay. It is super close to Mt Snow (6 minutes) but since we’ve had all our bookings at the Stratton Mountain- we went there ( about 20 minute drive which was super fast and convenient). Very clean home with clean bathroom and sheets. My kids didn’t want to leave. Justin was always responsive and very friendly. But there weren’t any issues we needed to contact him about. Would come back again. It was a perfect winter break for us. Thank you Justin and Adriana.

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

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

3br/2ba Family Friendly home- 1mi from the track!
Brooke's place is a good size...lots of room and so many nice touches (especially the abundant amenities provided for a small child). Very clean. Just as pictured. All good. The only thing I'd say as a bit of info to a prospective Airbnb-er, is that this location is not a walk to town spot, unless you consider 1.7 miles to the main shopping/dining area walkable. That said, it is still incredibly convenient...super quick drive to town or to race track or the lake...all while staying in a quiet, woodsy neighborhood setting.

Sunny Decks with Views in Stockbridge!
we stayed for the Thanksgiving holiday to have more space for family and friends to visit. this was definitely the nicest Airbnb we have stayed in and would highly recommend it if you plan to stay in the Berkshires. you are within minutes to everything you might need but secluded enough for you to feel like you're the only ones there. we loved the fire pit and the house is spacious and beautiful. the house had some really neat features as well such as the old antique music box was super cool and played with the most amazing sound. we will be back.

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!

Farmhouse and Guesthouse w Pool, Pond and Sauna!
Donna was an amazing host and extremely responsive. The property was beautiful and exactly as described in the listing. The pool, pond, sauna’s made the entire experience feel like a special escape from the city. I highly recommend this property and can’t wait to go back!
Pet-friendly home rentals with a pool

Leonard’s Log - Private Hot Tub, Fire Pit, A/C
This was the second time I booked Erin’s place and my group and I loved it! The outdoor jacuzzi is a huge highlight. The house is spacious and very comfortable.

Hudson Hill House - Sun & Fun w/ Pool near Hudson
I had an incredible stay. The house is tucked away in the woods and feels very peaceful. The house itself is beautifully and tastefully decorated. It’s spacious and comfortable. The host was responsive and welcoming. I would most definitely return!

Modern Barn with Loft at House on Golden Hill
We had a great time - coming from the city, it was a perfect rural getaway for us. It was also a short drive to downtown Lenox. Thank you for a lovely stay!

Modern Barn on 12 acres w Sauna, FirePit+swimming
there was lots to do inside the house as well as outside. everything was amazing

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm
We had an excellent experience with Todd and his cottage. It was a perfect weekend getaway. The space was very quiet and peaceful but close to local attractions. Todd had great recommendations for restaurants, shops, wineries, breweries, and other activities, all of which were no more than 10 minutes from the cottage via car. The space was small but appeared exactly as described in the listing. It was a perfect option for us and our dog. We would definitely return in the future!

Country Getaway Tiny House in Woods w/Pool/Sauna.
House was very clean and comfortable. Loved the decor and bed was super comfortable and cosy. Everything was there in the house- kitchen, bathroom, hot water. Well styled decor. Spotless. Felt very private and peaceful. Location was not as picturesque as I prefer, but fairly close to sight seeing.

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.

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
Mike's place was perfect for a large group looking to ski or snowboard. Mike was extremely responsive. The house was huge and filled with games to keep everyone entertained. We would definitely recommend this space.
Private, pet-friendly home rentals

Country hideaway
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

A Magic Spot: Booking year round.
the airbnb is very homey, well stocked, and easy to navigate. we had one slight issue with a mess that was not found by the cleaning crew, but robert was friendly and shared our concern about this.

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.

Cozy Country Cabin: Skiing,Hiking, fishing.
Thank you for hosting us for the weekend! We had the most relaxing stay, it was exactly what we needed. Truly never would have had to leave the property if we didn't want to. Perfect getaway.

Hudson: MV Buren 2 bedroom cottage Lake Property
Everything was exactly as it was in the Description. It was a bit tricky finding the exact location reason being it was dark out when we arrived. However, Ann & Francois were great and responded quickly and stood on the phone with us and guided us until we arrived at the front door. all-inall it was a very pleasant stay and experience. We will definitely look forward to another visit. I recommend this place to all who enjoy these types of experiences.

2 br apartment 12 mins to Mount Snow Unit #2
They were upfront about the noise, and it really wasn’t much of an issue at all. Certainly noise from others, but nothing for concern. Enjoyed our stay!

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.

Private guest apartment. One block from downtown.
The stay itself was wonderful! As advertised, it was well within walking distance from the downtown area, was cozy, and looked exactly like the pictures showed. 5/5 stars What pushed it over the edge from a good Airbnb to GREAT, was the attention Jennifer paid to small additional details - little chocolates to welcome us, snacks intentionally set out for us, water bottles, and a few other things speak to how good of a host she is. 6/5 stars 5/5 stars for Jennifer and her lovely apartment, 3/5 stars for Airbnb: we didn't get a message from Airbnb until we were checking out that her messaging wasn't working, so a couple messages went unanswered. Jennifer had put her number in 3 different locations explaining this, so she was super proactive, we were just a little unobservant in seeing that.
Quick stats about vacation rentals that are pet-friendly in Williamstown
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
2.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Magic Mountain Ski Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Berkshire East Mountain Resort
- West Mountain Ski Resort
- Saratoga Race Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Naumkeag
- Beartown State Forest
- Otis Ridge
- Hooper Golf Course
- Berkshire Botanical Garden
- Butternut Ski Area and Tubing Center
- Willard Mountain