Family-friendly vacation rentals in Hampshire County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Hampshire County

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

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Guest favorite

Guest suite in Granby

4.91 out of 5 average rating, 137 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.

Guest favorite

Guest suite in Northampton

4.86 out of 5 average rating, 490 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

Rental unit in Northampton

4.93 out of 5 average rating, 195 reviews

Light-bathed 3br w porch in best downtown location

Sun-drenched 2nd fl apt in 2-family Victorian home, steps from Northampton's vibrant downtown. Three spacious bedrooms: 2 with queen beds & a third with a double. Central eat-in kitchen with dining table, gas range and small dishwasher. Expansive south-facing living room with two couches and 42" smart HDTV. Private porch overlooking quaint tree-lined street. Wood floors throughout apartment. Hi-speed Internet. Laundry room in basement with free washer/dryer (shared with downstairs apt).

Guest favorite

Home in Williamsburg

4.99 out of 5 average rating, 177 reviews

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

Guest favorite

Rental unit in Pelham

4.99 out of 5 average rating, 138 reviews

Pelham 2nd floor Apartment

Second floor newly finished apartment that accommodates 2 guest. Well water and septic. Green by recycling and using salvage materials. Environmentally benign materials used where possible. Solar. Utilities and internet included. Raspberries and blueberries in season. 3.9 miles from UMASS and Amherst Colleges. 5.3 miles from Hampshire College. 11 miles from Mt. Holyoke and 12 miles from Smith College. NO PETS ACCEPTED! Allergy free. Don't hesitate to contact us with questions!

Guest favorite

Rental unit in Amherst

4.9 out of 5 average rating, 240 reviews

Amherst, Quiet, Private, Spacious Studio apartment

This airy, bright studio apartment is a short drive to the University of Massachusetts, Hampshire College, Amherst College, and Mt. Holyoke College in South Hadley and Smith College in Northampton. We are in the Pioneer Valley, a treasure trove of amazing views, forests and waterways as well as gourmet dining and music venues. We are about 2 miles to the Eric Carle Museum, the Yiddish Book Center, Emily Dickinson Museum, art museums and galleries as well as hiking trails.

Guest favorite

Guesthouse in Northampton

4.93 out of 5 average rating, 259 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

Rental unit in Plainfield

4.97 out of 5 average rating, 251 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Guest favorite

Rental unit in Williamsburg

4.88 out of 5 average rating, 196 reviews

Studio apartment on route 9, "Inn the Valley"

A bright and cozy studio apartment on PVTA bus line just outside of Northampton, MA. Skylight, wood floors, kitchen, and full bathroom as well as heat and air conditioning, oriental rugs and unique furnishings. 10 minutes from Northampton center and 20 minutes from Amherst center. Very convenient for all 5 colleges. Five minutes from Snow Farm Art Institute. Two minutes from Valley View Farm. We are meticulous in our cleaning and disinfecting in the face of Covid-19.

Guest favorite

Rental unit in Easthampton

4.91 out of 5 average rating, 177 reviews

Private Farm 1 BR Apartment, Close to Everything

Our farm is a quiet, 5+ acre haven one mile from the center of Easthampton and 8-12 minutes to Smith College/Northampton. It's a great base from which to explore all the restaurants, cultural and outdoor activities offered in the beautiful Pioneer Valley. The private apartment is on the first level of our rustic farmhouse and offers a kitchenette, living room, queen bedroom and bathroom. (An additional bedroom is also available-see separate listing for 2BR).

Guest favorite

Cottage in Ashfield

4.96 out of 5 average rating, 325 reviews

hope house

Sunny and open writing studio with over 150 years of literary history. Built in 1870, this lovely little house was where George Curtis edited Harper's magazine, wrote essays on transcendentalism , and argued for women's suffrage ( A recent guest informs me that George Curtis helped Thoreau build his cabin on Walden Pond ) The house has since sheltered painters, librarians, and poets.

Guest favorite

Rental unit in Northampton

4.92 out of 5 average rating, 579 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!