
Family-friendly vacation rentals in Williamstown
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Top-rated family-friendly rentals in Williamstown
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Williamstown family-friendly rentals
Family-friendly home rentals with a hot tub

Modern Home in Woods w/ Hot Tub 10 Miles to Hudson
The very much enjoyed our stay! We loved the uniqueness of the property and found it to be a perfect secluded place for our group trip. We loved using the hot tub and wood stove in the cold weather and the kitchen had everything we needed for preparing food for our group of 8. We’d happily stay here again!

Country Getaway Lodge / Ranch
Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.

Mt Snow Ski In/Out at Seasons
Andrew’s description and check in instructions were extremely detailed. Host was very easy to contact/communicate with and very accommodating. Clear instructions for check in/out, how to get to unit and how to ski in ski out. Unit description and photos are accurate. I would consider staying here in the future again.

Saratoga Escape
Had a great time at this beautiful home! Felt super peaceful and great for groups. Thanks so much!

Peaceful cabin close to skiing & Brattleboro
Our 4th time staying here. It is our preferred house to rent in southeastern VT. Feels like home staying here. House is warm, inviting, has a nice layout. Plenty of room to unwind. Nothing negative to say at all. Always a pleasure staying here. We will be back again.

Updated Colonial Close to Town Available All Year
Cleanly kept home. Hot tub works great (though panel can be hard to read). Little bit of road noise, not bad at all. Walkable to downtown if you cross over to Maple Ave. Basement layout is a bit quirky.

Private Apt on Farm, Hot Tub with views!
Such a great and unique stay! Beautiful area, great accommodations, and so cozy. We loved being on a large property with animals and the hot tub was wonderful. Robert is an excellent host with such a neat property! And the maple syrup fresh from their own trees was amazing!!! Highly recommend.

The Vermont Barn (Mount Snow)
We rented Brian’s home for a weekend getaway celebrate my husband’s birthday. The house is a converted barn which is cool and it was spotless. Everything was great despite the looming big snowstorm coming. It was quite the adventure for our family and so much fun. The house was perfect for our family of 8. It is way up on a mountain and right around the corner from a clubhouse with game room, gym, indoor pool and jacuzzi. I was a bit concerned about the weather coming and Brian was very responsive to my questions about the weather and any other questions I had. This weekend surely will be one the grandkids won’t soon forget about! Thank you Brian for renting your home to us!
Family- and pet-friendly home rentals

Columbia County Getaway - Raspberry Ridge Cottage
Laurence and Ilze’s cozy cottage is a hidden gem where my family of 4 and additional guests enjoyed our short stay. Their place is well stocked and has everything you need, like your home away from home. Its’s charming, comfortable clean, spacious and pet friendly with super friendly hosts. Added bonuses were their farm products which we purchased during our stay from fresh farm to table eggs, honey and maple syrup. We will definitely plan to stay in their cottage again in the future.

Cedar Wet Room w Soaking Tub
It was very peaceful, great get away from the city. Good for the dogs. The copper tub is amazing, we could not get enough of it. And the dual showers felt so good. It felt very homey. Mr. John was a a great host.

Guesthouse close to hiking, shopping and ski!
Donna's place was a wonderful weekend stay! Beautiful property and guest house. Well appointed and care for. Just a few improvements that would have made our stay even better--a small microwave for quick reheating of coffee/leftovers, a luggage rack and place to store/hang clothes, and ensuring the driveway and a walking path are cleared of snow even when out of town (with thawing and refreezing, we had to navigate two inches of solid ice, which was terrifying both on foot and in the car).

December in Peaceful Vermont (Pet Friendly)
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

Entire HOUSE Walk to ALL Dogs OK
Nancy’s place was a great option for my stay in the area. The kitchen had everything I needed, and the couch was comfortable. As was the one bed I slept in. I was visiting for a work trip. Nancy was also incredibly responsive to any questions I had, and was offering suggestions for the area I found useful. I’m glad to have found this place. While on this trip, I did not bring my dogs, I will be sure to stay here on my next one to the area. I typically stay in hotels here, but I will do my best to stay at Nancy’s anytime visiting in the future.

Apple Blossom Cottage: A Tiny House
Beautiful little place in Vermont with tons of good food close by and such a short travel to the skiing mountains. I would definitely recommend checking it out

Peaceful Getaway - 12 Mins to Saratoga Race Track
We had a lovely stay! Dan and Shannon were super professional and friendly! Serene and peaceful location! Would highly recommend!

2 blocks to Warren ST w/ a yard and parking
We had a great stay! The place was clean, spacious, and very peaceful. It’s in a great location- walkable and close to the main drag. We also really appreciated the thoughtful recommendations on things to do in the area. Overall, a wonderful experience and would recommend!
Family-friendly home rentals with a pool

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

The Creation Station
john is a fantastic host and wonderful guy- i would recommend his place to anyone.

Saratoga Springs convenient tranquil location.
We had a lovely Labor Day weekend stay at Julie’s house. There was lots of space indoors and out. The hot tub, pool, fire pit, and grill were all put to good use and made our stay so homey and comfortable. The kitchen was well stocked with all the tools and appliances needed. The location is excellent with easy access to 87, SPAC, and the race track.

Modern Barn on 12 acres w Sauna, FirePit+swimming
The house and the barn were the perfect spot to gather family scattered between Baltimore and Albany. We had planned on visiting Art Omi but the weather didn’t cooperate, but the house was such a lovely space that we had no reason to leave! We even got a little show from two adult and one juvenile bald eagles! Lovely home, would absolutely recommend!

Berkshire Lake House, gunite pool, Chef's Kitchen
Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!

Great Saratoga House with Pool Walk to Everything!
Loved staying here! It was super cozy and a lovely home away from home for the holidays. House is as described and very spacious. Fireplace makes it extra cozy when the weather got cold. Host was very proactive and responded to any question or issue almost immediately. We will definitely be staying here again!

Cozy Condo @ Jiminy Peak
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

1880s sun-bathed beauty in best downtown location
We loved this space. Very clean, convenient & very comfortable and a great value. We will be back.
Quick stats about vacation rentals that are family-friendly in Williamstown
Total rentals
80 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
3.8K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
80 properties include access to wifi
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