Family-friendly vacation rentals in Southwick

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Southwick

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

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Guest favorite

Bungalow in Easthampton

4.92 out of 5 average rating, 476 reviews

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Guest favorite

Chalet in Otis

4.95 out of 5 average rating, 382 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Guest favorite

Home in Granby

4.95 out of 5 average rating, 242 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

Clean refreshing three-bedroom , one floor living, centrally located, walk to town for fantastic dining ! Mexican, Sushi and Thai, Mediterranean, Italian, Continental, and Vegan ! 8 minutes to rt 91 and Bradley, minutes to Mass line! Downstairs living space with a gameroom and comfortable seating, and extra sofa bed and airbeds, if needed. Other than clothes, you will need nothing else...I provide everything from razors to coffee , tea and a HUGE snack basket ! Even have a heating pad .

Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 504 reviews

Separate apt, 1 mile from downtown, 1 guest only

This is a private, clean, comfortable apartment with New pillow top mattress for 1 person with separate entrance in our new home. You will have the space to yourself. We are a mile from downtown near the bike path, the mill river, and Smith college. Private bathroom with a shower; kitchen basics: fridge, microwave, toaster, teapot, pour over coffee. Wifi and smart tv. Sunny with central air in the summer warm and cozy in the winter. Walk or ride a bike to town. We’re located in Village Hill.

Guest favorite

Cabin in Cummington

4.98 out of 5 average rating, 196 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Guest favorite

Home in Chester

4.96 out of 5 average rating, 337 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Guest favorite

Guesthouse in Northampton

4.93 out of 5 average rating, 262 reviews

Large Studio – Walk to Town

IMPORTANT: Please read the full description about the eco-friendly policy and click the "CONTACT HOST" button, rather than making a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

Guest favorite

Home in Feeding Hills

4.89 out of 5 average rating, 931 reviews

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, good for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Guest favorite

Rental unit in Amherst

4.9 out of 5 average rating, 247 reviews

Amherst, Quiet, Private, Cozy Studio Apartment

This cozy studio is ideally located for exploring nearby colleges: UMass, Hampshire, Amherst, Mount Holyoke, and Smith. Nestled in the scenic Pioneer Valley, enjoy stunning landscapes, forests, and rivers, as well as cultural highlights like the Eric Carle Museum, Yiddish Book Center, and Emily Dickinson Museum. Just minutes from hiking trails, art galleries, gourmet dining, and music venues, our studio offers the perfect base for your Pioneer Valley adventure.

Guest favorite

Home in Russell

4.96 out of 5 average rating, 244 reviews

South Quarter House

Built in the early 1800s, our renovated farm house can accommodate families and friends comfortably. This 1600 square foot home can keep everyone together: three large bedrooms upstairs and an optional fourth downstairs. Large backyard and deck made for outside fun. Two full bathrooms, laundry, large farm table with seating for 10, and a full kitchen. Plenty of options for hiking at or near the house. (Sorry, we are not able to host weddings.)

Guest favorite

Guesthouse in Granby

4.89 out of 5 average rating, 228 reviews

The Loft @ Lost Acres ~ A Peaceful Rural Escape!

The Loft @ Lost Acres Vineyard is a wonderfully private, rural getaway! This bright and comfortable space is located on the upper floor of a Lost Acres Vineyard barn. Originally intended for the caretaker, the owners are now offering it to the public to enjoy the beauty of the vines & the stunning rural scenery of North Granby. Oh, and stop by the tasting barn, the wine is AMAZING!

Guest favorite

Rental unit in Winchester

4.91 out of 5 average rating, 369 reviews

Gateway to the Berkshires

Remodeled apartment on 2nd floor of a 1910 Victorian house near the center of Winsted, CT. The apartment is unique and cozy, with large windows, some stained glass, tin ceilings, hand painted kitchen cabinets, and plants. Close proximity to all Litchfield County and the Berkshires have to offer, in all seasons. It's an easy drive from NYC or Boston. Great weekend get-away.