Family-friendly vacation rentals in Williamstown

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Popular amenities for Williamstown family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite

Farm stay in Valley Falls

4.89 out of 5 average rating, 223 reviews

Country Getaway Lodge / Ranch

TrevorRating, 5 stars1 month ago
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.
Guest favorite

Condo in Dover

4.87 out of 5 average rating, 234 reviews

Mt Snow Ski In/Out at Seasons

TaraRating, 5 stars1 month ago
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.
Guest favorite

Home in Saratoga Springs

4.81 out of 5 average rating, 120 reviews

Saratoga Escape

KimberlyRating, 5 stars3 months ago
Had a great time at this beautiful home! Felt super peaceful and great for groups. Thanks so much!
Superhost

Home in Northampton

4.88 out of 5 average rating, 626 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

AcRating, 5 stars2 weeks ago
Had a lovely quiet evening in this spot, wish I’d been able to stay longer!
Guest favorite

Home in Newfane

4.98 out of 5 average rating, 133 reviews

Peaceful cabin close to skiing & Brattleboro

AlexanderRating, 5 stars3 weeks ago
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!
Guest favorite

Home in Saratoga Springs

4.98 out of 5 average rating, 121 reviews

Updated Colonial Close to Town Available All Year

TylerRating, 5 stars3 months ago
Great home in a great location. Highly recommend for any groups looking to visit Saratoga Springs.
Superhost

Apartment in West Townshend

4.9 out of 5 average rating, 335 reviews

Private Apt on Farm, Hot Tub with views!

Eva & PeterRating, 5 stars1 month ago
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!
Guest favorite

Home in Wilmington

4.83 out of 5 average rating, 166 reviews

The Vermont Barn (Mount Snow)

AmyRating, 5 stars1 month ago
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

Guest favorite

Home in Great Barrington

4.94 out of 5 average rating, 126 reviews

The Hideaway: Berkshire Home - village of Egremont

LeahRating, 5 stars2 weeks ago
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.
Guest favorite

Cottage in Craryville

4.91 out of 5 average rating, 523 reviews

Columbia County Getaway - Raspberry Ridge Cottage

DrewRating, 5 stars1 month ago
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.
Guest favorite

Apartment in Northampton

4.95 out of 5 average rating, 242 reviews

Cedar Wet Room w Soaking Tub

AlexRating, 5 stars2 weeks ago
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.
Guest favorite

Home in Ghent

4.9 out of 5 average rating, 280 reviews

Renovated guesthouse on 52 acres!

KatyRating, 5 stars1 month ago
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!
Guest favorite

Home in Saratoga Springs

4.8 out of 5 average rating, 160 reviews

Entire HOUSE Walk to ALL Dogs OK

EdelRating, 5 stars4 months ago
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.
Guest favorite

Tiny home in Jamaica

4.94 out of 5 average rating, 1,234 reviews

Apple Blossom Cottage: A Tiny House

RebeccaRating, 5 stars1 week ago
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!
Guest favorite

Apartment in Saratoga Springs

4.91 out of 5 average rating, 265 reviews

Cody Farms Private Spacious Apartment - No Cln Fee

CatherineRating, 5 stars2 weeks ago
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!
Guest favorite

Vacation home in Hudson

4.89 out of 5 average rating, 113 reviews

2 blocks to Warren ST w/ a yard and parking

BrianRating, 5 stars1 month ago
lovely, charming, tastefully appointed place. more importantly, the most caring and responsive hosts i have ever had.

Family-friendly home rentals with a pool

Superhost

Guest suite in Saratoga Springs

4.87 out of 5 average rating, 15 reviews

Home Away from Home

RobRating, 5 stars4 months ago
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.
Guest favorite

Townhouse in Dover

4.96 out of 5 average rating, 145 reviews

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

JulieRating, 5 stars2 weeks ago
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.
Guest favorite

Bungalow in Easthampton

4.92 out of 5 average rating, 487 reviews

The Creation Station

MarcRating, 5 stars3 weeks ago
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!
Guest favorite

Home in Saratoga Springs

4.86 out of 5 average rating, 110 reviews

Saratoga Springs convenient tranquil location.

ArickaRating, 5 stars5 months ago
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.
Guest favorite

Home in Ghent

4.88 out of 5 average rating, 310 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

TaraRating, 5 stars2 days ago
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!
Guest favorite

Home in Canaan

4.99 out of 5 average rating, 84 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

SueRating, 5 stars3 months ago
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!
Guest favorite

Home in Saratoga Springs

4.95 out of 5 average rating, 39 reviews

Great Saratoga House with Pool Walk to Everything!

CaitrinRating, 5 stars1 month ago
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!
Guest favorite

Condo in Hancock

4.85 out of 5 average rating, 146 reviews

Cozy Condo @ Jiminy Peak

SiriRating, 5 stars1 month ago
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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