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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 106 reviews

Berkshire Pontoosuc Lake- Modern and Updated

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Superhost

Home in Otis

4.94 out of 5 average rating, 142 reviews

Berkshires hideaway! Hikes & serenity near lake

Welcome to your light-filled home in the Berkshires. With a two-level wraparound deck & open floorplan, you can enjoy your time together, away from the world. Big spaces and cozy spots throughout. Perfect for families (with a swingset!) or getaways with friends. Otis Reservoir, MA's biggest lake, is nearby. Audubon preserve behind the house. Great, private home base for hiking, summer music/dance/theatre, trips to Kripalu or MassMOCA, skiing... or for going nowhere at all. Dogs OK! (note: fee)

Superhost

Home in Egremont

4.95 out of 5 average rating, 106 reviews

Bucolic Berkshires House~Hiking Heaven

UNIQUE, bright, open space with a great kitchen and thoughtfully decorated. Near MANY exciting destinations such as skiing, cultural and arts destinations, vineyards, antiquing, you name it, in both the Berkshires and Hudson Valley. Located on an unpaved road and adjacent to a beautiful park and a nearby lake. There's so much to do, but if you'd prefer to take a more relaxed approach to your get-away then shop the wonderful local food stores and farms and enjoy cooking and our lovely house.

Guest favorite

Home in Holyoke

4.97 out of 5 average rating, 322 reviews

Explore Holyoke from this charming 3 Bedroom house

This house is settled in a quiet residential neighborhood.Guests have access to the entire second floor,one flight of stairs and you're in.There are lots of windows that brighten the space,with a large dining room,office desk, and a newly renovated bathroom.The living room leads to a beautiful spacious porch over looking the park/playground.All bedrooms have comfortable matresses,lots of pillows, soft sheets,thick super soft towels. Smart TV (Netflix/hulu/sling/roku)

Guest favorite

Condo in Dover

4.87 out of 5 average rating, 228 reviews

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

Guest favorite

Rental unit in Northampton

4.92 out of 5 average rating, 592 reviews

Sunny Peaceful Home

This is a home-away-from-home! The space includes a full kitchen, laundry, wireless Internet, a queen-size bed, and more. Located in a safe, quiet, residential neighborhood, there is a river out back for swimming and many books and toys in the apartment if you're traveling with small children. You'll also have a beautiful view of the river from the 2nd-floor back deck!

Guest favorite

Home in Dover

4.87 out of 5 average rating, 237 reviews

Mt Snow retreat, ski & summer

Warm and welcoming space for relaxation and play, your home base for VT recreation. 7 min. drive to Mount Snow, convenient location. Easy access to hiking, mountain biking, x-c skiing, golf course, and more! Sleeps 5 easily. ~10 min. walk to Moover, 7-11, restaurants. INTERNET - There is a fiber optic connection and the plan speed is 50Mbps down / 30Mbps up.

Superhost

Rental unit in West Townshend

4.91 out of 5 average rating, 327 reviews

Private Apt on Farm, Hot Tub with views!

Taft Hill Farm stay in a private 2-bedroom apartment plus sleeping loft, open-plan kitchen, living space; separate entrance; best views in Vermont! A great retreat for a family, a couple or a group of friends. Apartment is attached to main farmhouse on a historic 38-acre hillside farm. Extensive gardens & orchard, heritage breed cows, chickens and sheep.

Guest favorite

Cabin in Wilmington

4.93 out of 5 average rating, 441 reviews

Picturesque Cabin near Mt Snow

Enjoy fall in Vermont! Our cabin is the perfect spot to experience cozy VT charm without missing out on modern amenities. The beautiful Green Mountains are right outside our door as well as nearby lakes and rivers. The cabin is well equipped with 3 bedrooms, 1 bath; and you'll love the screened-in porch out back. We’re also dog-friendly!

Superhost

Cabin in Otis

4.86 out of 5 average rating, 413 reviews

Cozy cabin in the Berkshires

UPDATE: We have broadband!! Cozy and peaceful Scandinavian inspired post and beam cabin. simple, unfussy. Near many wonderful Berkshires activities. Minutes from Jacobs Pillow, lakes, ponds, hiking, biking, skiing. amazing local food and farms. Perfect country retreat for a weekend, a week or the whole month. sleeps up to 4.

Guest favorite

Home in Egremont

4.98 out of 5 average rating, 125 reviews

A sunny, quiet chalet beautifully decorated.

Welcome to our modern and sunny chalet nestled in the woods. Located directly across the street from Catamount Mountain Resort for year-round fun. Numerous hiking trails nearby, and Great Barrington’s dining and shopping minutes away. Relax in style and comfort and make unforgettable memories with friends and family. l

Superhost

Rental unit in Great Barrington

4.94 out of 5 average rating, 142 reviews

GB Eclectic Victorian

First floor renovated mini victorian with back patio. Deep soaker tub and walk in glass shower. Brand new kitchen with gas stove. Sleeps 4 one queen bed one full size bed 2 Miles from Butternut Ski area and 10 to Catamount. Close to downtown Great Barrington and Tanglewood. No pets, no smokers seasonal rental option.