Family-friendly vacation rentals in Pioneer Valley

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Pioneer Valley

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

The exterior of a two-story house is displayed, featuring a wide front porch with multiple windows. A well-maintained lawn is positioned in front, bordered by shrubs. The home includes a stone accent and a double garage, all set against a backdrop of trees.

Guest suite in Granby

4.91 out of 5 average rating, 144 reviews

Whole place,staycation,3 bedrooms, spacious area

ENTIRE LIVING SPACE: Private spacious 3 bedroom lower level. Near MacDuffie Prep School & 5 prestigious colleges. Couples, solo adventurers, business travelers, families (with kids), and big groups. 14 acre. Private-golf course, pickleball, polypropylene basketball court, badminton, fishing, frisbee golf and tennis courts close by. Nature surrounds you with quiet locations to relax. 1 acre beach pond to cool off. If you are the person who likes to stay busy or relax, this is the place for you.

Top guest favorite

A bright entryway features a white wall with hooks for hanging items and a woven basket atop a built-in bench. Light enters through a nearby window, illuminating the space. A simple blue area rug adds a touch of color, and a door leads outside.

Home in Pittsfield

4.97 out of 5 average rating, 115 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!

Superhost

A backyard playset is situated on lush green grass, featuring a swing set with two swings and a slide. A small playhouse with a sloped roof can be seen nearby, surrounded by trees providing a natural and shaded environment.

Home in Otis

4.94 out of 5 average rating, 144 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)

Top guest favorite

A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.

Apartment in Wilmington

4.91 out of 5 average rating, 134 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.

Guest favorite

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favorite

A cozy living area is highlighted by hardwood floors and large clerestory windows. A wooden entertainment console with a television sits beside a lamp with a soft glow. Decorative shelves display books and art, creating an inviting corner next to a wicker chair.

Cottage in Amherst

4.93 out of 5 average rating, 161 reviews

Beautifully Restored Cottage Studio

Originally built as an artist's studio, our Private Cottage is a fully-restored, light-filled, wonderfully serene space - with plush and thoughtful designer-appointed furnishings, cathedral ceilings, hardwood floors, a renovated en-suite bath, and a complete kitchen. Freshly laundered 450+ thread count Egyptian cotton beddings, linens, and towels are provided on-site as are complimentary amenities. * Fully Private, Quiet & Serene, Family-Friendly * An easy 3-minute drive to town

Top guest favorite

A play area located in a grassy yard features a wooden playset with a slide and climbing wall, accompanied by a trampoline nearby. Lush trees provide a natural backdrop, creating a recreational space suitable for children.

Home in Holyoke

4.97 out of 5 average rating, 328 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)

Top guest favorite

Home in Brimfield

4.94 out of 5 average rating, 164 reviews

Brimfield Lakeside Home Away from Home

Renovated Brimfield Lakeside Home: minutes to downtown Brimfield & Sturbridge offers two bedrooms plus additional upstairs loft sleeping area, one bath & sleeps six. We are a year round property located in a quiet cove on beautiful Little Alum Pond in Brimfield, Massachusetts. Extremely tranquil setting, yet plenty of great restaurants and shopping are just minutes away.

Top guest favorite

A bright corner of the studio features a white table surrounded by plants on shelves and window sills. Natural light filters through curtains, illuminating an array of children's toys and books on nearby shelves. A simple chair complements the workspace.

Apartment in Northampton

4.92 out of 5 average rating, 620 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!

Superhost

The cabin's exterior is surrounded by lush greenery, showcasing wooden siding and a well-maintained deck. Outdoor seating is provided on raised steps, while a patio area features a small table and chairs. An umbrella offers shade for relaxation during sunny days.

Cabin in Otis

4.86 out of 5 average rating, 416 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

A bright living area features a white sectional sofa facing a brick fireplace, complemented by a green wall decoration. Large windows allow natural light to illuminate the space, with soft green plants providing a touch of nature. A small wooden table sits nearby.

Home in Sunderland

4.96 out of 5 average rating, 121 reviews

Iconic New England Home

This is a spacious arts and crafts style home. 5 bedrooms, 3 baths, 3 living rooms, modern kitchen, huge screened-in front porch couples with beautiful woodwork, fireplace and outdoor area. Walking distance to award winning Blue Heron Restaurant and more. May graduation weekends are a four night minimum stay.

Guest favorite

A chalet-style cabin is surrounded by trees, featuring a large wooden deck with several colorful adirondack chairs. Bright yellow double doors stand out against the green exterior, while large windows provide views of nature.

Cabin in Wilmington

4.93 out of 5 average rating, 448 reviews

Picturesque Cabin near Mt Snow

Enjoy winter in Vermont! Our cabin is the perfect spot to experience cozy VT charm without missing out on modern amenities. Only 15 minutes from Mount Snow ski resort. 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!