Family-friendly holiday 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.

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Guest favourite

Home in Saratoga Springs

4.98 out of 5 average rating, 172 reviews

5 Mins to Track, SPAC & Skidmore! Walk to Broadway

This bright & beautiful 2 bedroom home is located in Downtown Saratoga Springs near it all. A comfortably cozy home for guests of all ages! It's a 2-minute drive to Broadway (or 10-min walk) and a 5-min walk to the Beekman Arts District. You'll be within a 5-min drive to Saratoga Racetrack, SPAC, Skidmore, Universal Preservation Hall, City Center, Farmer's Markets and more. Stay here and you won't need a car to explore the best restaurants, bars, boutiques, parks and incredible nightlife!

Guest favourite

Home in Pittsfield

4.97 out of 5 average rating, 112 reviews

Berkshire Lake- Modern and Updated-close to skiing

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!

Guest favourite

Flat in Rexford

4.96 out of 5 average rating, 359 reviews

Need a Getaway??

It’s Fall foliage season! Apple picking & hiking, This ideal location is perfect for leaf peeping, visiting family, business travelers, college visits and lots of outdoor recreation. Located about 20 minutes from Saratoga’s city line. This beautiful, quiet and spacious apartment on the 2nd floor overlooks several acres of land. Also, a perfect halfway point between Canada and New York City. We offer complimentary coffee, eggs & pancake mix to cook in the full size kitchen. Pool is heated!

Guest favourite

Flat in Wilmington

4.91 out of 5 average rating, 130 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Superhost

Home in Jamaica

4.86 out of 5 average rating, 288 reviews

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a convenient setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Guest favourite

Home in Athens

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favourite

Home in Salem

4.98 out of 5 average rating, 189 reviews

Magical Farm Getaway - a must visit!

Beautifully restored 18th century farmhouse situated on 4.6 private acres within a 180 acre working farm. Five bedrooms, wood stoves, ample living space, and a cheery sun room with gorgeous views make this house one of a kind. Our backyard features an in-ground, heated, salt water swimming pool (open May to mid-Oct), fire pit (open year-round), large outdoor dining table, gas grill, and a deck with lounge seating and jacuzzi (open year-round). Parties and events are not allowed.

Guest favourite

Cabin in Hillsdale

4.89 out of 5 average rating, 103 reviews

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

Guest favourite

Flat in Northampton

4.92 out of 5 average rating, 606 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 favourite

Home in Dover

4.88 out of 5 average rating, 243 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.

Guest favourite

Home in Egremont

4.98 out of 5 average rating, 131 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. Please not that we do not allow pets.

Superhost

Cabin in Otis

4.86 out of 5 average rating, 415 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.