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Family-friendly vacation rentals in Williamstown
Find and book unique family-friendly homes on Airbnb
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
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Farm stay in Valley Falls
4.89 out of 5 average rating, 223 reviewsCountry 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.
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Condo in Dover
4.87 out of 5 average rating, 234 reviewsMt Snow Ski In/Out at Seasons
Great experience renting from Andrew. Very responsive, within minutes any time we reached out. Place was super convenient to get to the slopes. Locker outside the front door was convenient as well to keep our snowboards and skiis. Our family had a great time in Mt. Snow and hope to be back.
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Home in Saratoga Springs
4.81 out of 5 average rating, 120 reviewsSaratoga Escape
Had a great time at this beautiful home! Felt super peaceful and great for groups. Thanks so much!
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Home in Northampton
4.88 out of 5 average rating, 626 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Had a lovely quiet evening in this spot, wish I’d been able to stay longer!
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Home in Newfane
4.98 out of 5 average rating, 133 reviewsPeaceful cabin close to skiing & Brattleboro
Our group had a fantastic time here! it was secluded and private. The wood stove was particularly nice given that it snowed a little bit while we were there. Given its location, we still never felt too far away from anything we wanted. Brin was always just a message away if we needed too, fantastic host and a beautiful home. We'll keep this place in mind for future gatherings!
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Home in Saratoga Springs
4.98 out of 5 average rating, 121 reviewsUpdated Colonial Close to Town Available All Year
Great home in a great location. Highly recommend for any groups looking to visit Saratoga Springs.
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Apartment in West Townshend
4.9 out of 5 average rating, 335 reviewsPrivate Apt on Farm, Hot Tub with views!
We had a beautiful time as Roberts home is so peaceful with the incredible winter views! It was a frigid weekend so unfortunately we couldn’t really enjoy the hot tub even though we did venture in it for a quick 15 minutes . Do not recommend doing this in negative wind chill! The apartment had everything we needed for a cozy stay. Robert met us at the parking area and gave us a great recommendation for dinner - the Grafton Inn Barn Pub restaurant was so quaint in a an old barn with a fire going in their two story fireplace. What a treat also to learn what an incredible glass blowing artist Robert is. We visited his gallery workshop and watched him and his assistants create glass bowls and purchased a colorful glass pumpkin and an ornament. We loo forward to our next visit when we can see the farm and animals in full bloom!
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Home in Wilmington
4.83 out of 5 average rating, 166 reviewsThe Vermont Barn (Mount Snow)
The barn, was absolutely perfect for a ski weekend. It felt like we were living in a snow globe with the weather. The hot tub was clean and the beds were all very comfortable. The house easily accommodated our group. The driveway and surrounding roads in the community do require 4wd or awd in the winter season.
Family- and pet-friendly home rentals
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Home in Great Barrington
4.94 out of 5 average rating, 126 reviewsThe Hideaway: Berkshire Home - village of Egremont
This was the second time staying in this house with another family. Can't beat the convenient location to local mountains for skiing. House is spacious and plenty of room for two families of 4. Shiyrah is friendly and communicative.
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Cottage in Craryville
4.91 out of 5 average rating, 523 reviewsColumbia 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.
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Apartment in Northampton
4.95 out of 5 average rating, 242 reviewsCedar 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.
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Home in Ghent
4.9 out of 5 average rating, 280 reviewsRenovated guesthouse on 52 acres!
Perfect spot for a cozy winter escape. The clawfoot bathtub and wood stove (inside) + the fire pit and wood sauna (outside) make for the perfect getaway. We loved all of the beautiful design features of the guesthouse (a-frame ceiling, exposed beams, original wide-plank floors), and tons of thoughtful touches throughout (well-stocked kitchen with lots of teas and coffee, drinks available to purchase, bluetooth speaker for putting music on, games, bathroom products, etc). Great location near Bartlett House and Art Omi and a quick drive from Hudson, Kinderhook, and other neighboring towns. Donna was super helpful and welcoming. Thanks for a great stay!
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Home in Saratoga Springs
4.8 out of 5 average rating, 160 reviewsEntire HOUSE Walk to ALL Dogs OK
Nancy was a great host from the second we booked her listing. Her home was immaculate and the perfect location for our weekend away. Nancy provided us with so many recommendations on local restaurants, bars, spas etc. A home away from home. We can’t wait to visit again, thanks again.
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Tiny home in Jamaica
4.94 out of 5 average rating, 1,234 reviewsApple Blossom Cottage: A Tiny House
So close to Stratton, the perfect spot for a quick ski trip. Helpful communication and instructions from the host made everything quick and easy. Would definitely stay again!
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Apartment in Saratoga Springs
4.91 out of 5 average rating, 265 reviewsCody Farms Private Spacious Apartment - No Cln Fee
This place is a gem! Exactly like it looks in the photos and great tips from the hosts. It’s ideal for a cozy and scenic getaway and close enough to downtown to go shopping or get dinner while being far enough away to feel in nature. We’ve been here a few times over h the years and look forward to visiting again someday!
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Vacation home in Hudson
4.89 out of 5 average rating, 113 reviews2 blocks to Warren ST w/ a yard and parking
lovely, charming, tastefully appointed place. more importantly, the most caring and responsive hosts i have ever had.
Family-friendly home rentals with a pool
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Guest suite in Saratoga Springs
4.87 out of 5 average rating, 15 reviewsHome Away from Home
Devra & her daughter were great hosts. Devra entered the Suite with me, pointed out everything I needed to know. She is an interior decorator & her talents were displayed in the Suite. Newly renovated with oversized bedroom & bathroom. Living room conveniently connected to the kitchen. I’ve been renting in Saratoga for over a decade & it was the best location I’ve had. Walking distance to Track & Broadway. Easy bike ride to Saratoga Park.
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Townhouse in Dover
4.96 out of 5 average rating, 145 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Great place to stay for skiing. Very close to Mt. Snow. Matt was very quick to respond to any questions. The place was well equipped. The fireplace was great and added so much coziness.
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Bungalow in Easthampton
4.92 out of 5 average rating, 487 reviewsThe Creation Station
Unlike anything I have ever seen! My husband and I decided to go to Vermont to elope and we were looking for a unique place to stay within an hour distance. We weren’t able to arrive to the property until late, but John was very patient and let us in with a smile. The space itself was very clean and put together nicely. The sleeping arrangements were so comfortable that we overslept! We will be staying here again. Thanks John!
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Home in Saratoga Springs
4.86 out of 5 average rating, 110 reviewsSaratoga 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.
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Home in Ghent
4.88 out of 5 average rating, 310 reviewsModern 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!
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Home in Canaan
4.99 out of 5 average rating, 84 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
The house is charming but the beautiful collection of both vintage and antique pieces make it an exciting and warm home. It's fun just to walk around and look at all the pieces in the nooks and crannies. Most importantly it is warm and welcoming and was the perfect place to gather our family for my son's wedding weekend. The beautiful kitchen with it's rambling island was the anchor for many meals and conversations especially the late snack after returning from the wedding. The view of the lake from the dining room early in the morning was breaktaking. I can't say enough about the house! I was sad to leave it!! It's just a very special place! Meredith and Jason were very responsive to offer inquiries and flexible to our requests. They were perfect hosts!
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Home in Saratoga Springs
4.95 out of 5 average rating, 39 reviewsGreat 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!
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Condo in Hancock
4.85 out of 5 average rating, 146 reviewsCozy Condo @ Jiminy Peak
Wonderful condo - so easy to communicate w Dawn. She is resourceful and helpful! The condo unit is an end unit with the ability to walk to the ski resort as well as the Country Inn hotel. Husband used the hotel hot tub and said the hot tub was great. Pool was good too - outside pool in the winter is always a treat! Lots of bedding options in the condo - one of my teenagers slept on the couch and said it was amazing. Full kitchen capabilities and good coffee maker. :) Thanks again for a great weekend escape!
Quick stats about vacation rentals that are family-friendly in Williamstown
Total rentals
90 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
3.9K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Wifi availability
90 properties include access to wifi
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