Family-friendly holiday rentals in Northampton

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Top-rated family-friendly rentals in Northampton

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

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Guest favourite

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.

Guest favourite

Home in Pittsfield

4.97 out of 5 average rating, 110 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

Farm stay in Marlboro

4.88 out of 5 average rating, 616 reviews

Carriage Barn - Marlboro

Our place is within easy reach of Mt Snow, Carinthia, Marlboro Music Festival, and the super sweet town of Brattleboro. The 2-level apartment is entirely private and self-contained. Bonus offerings include an abundance of fresh country air and proximity to miles of woods trails. It's ideal for couples, solo travelers, and it's pet-friendly too. A short walk through the woods brings you to a spring-fed lake that is quiet and pristine. Winter, spring, summer, fall. Each season has its own magic.

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)

Guest favourite

Home in West Brattleboro

4.88 out of 5 average rating, 146 reviews

Cozy Home for 2-5 People in Vermont

Comfortable house for 2 to 4 people (two queen-sized beds) and a pull-out couch for a 5th person and a self-inflatable bed. Located in a quiet neighborhood. There are two main bedrooms with queen beds in each. There is also a pull-out couch in the room with the fireplace though it is not as comfortable as the self-inflatable bed (and deflatable) in the house. Fast Wi-Fi from Xfinity. Easy to get into Brattleboro Center and an excellent location for exploring Southern Vermont.

Guest favourite

Guest suite in Charlemont

4.9 out of 5 average rating, 200 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Superhost

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

December in Peaceful Vermont (Pet Friendly)

Country Home, nestled in the Green mountains, panoramic views, with access to the road. A babbling brook to lull you asleep from the master bedroom, a clawfoot soaking tub, stocked house. Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Enjoy Vermont! Scenic roads, nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires. Bennington Wilmington. PEACEFUL & PERFECT Vermont getaway! ☺

Guest favourite

Home in Holyoke

4.97 out of 5 average rating, 323 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 favourite

Apartment in Northampton

4.92 out of 5 average rating, 600 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

Cabin in Otis

4.86 out of 5 average rating, 414 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 favourite

Home in Sunderland

4.96 out of 5 average rating, 122 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.