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Kid-friendly holiday rentals in The Berkshires

Find and book unique family-friendly rentals on Airbnb

Top-rated family-friendly rentals in The Berkshires

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

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Cottage in Greenwood Lake

4.85 out of 5 average rating, 191 reviews

Cozy Cottage | HotTub & Family Rm | 1H fr NYC

Just a little more than an hour away from NYC and a 4-min drive to the lake, this pet-friendly private retreat offers a hot tub, family room, spacious yard with fire pit, and a deck with a grill and comfy seating. The renovated interior has all the comforts of home including a full kitchen & streaming capabilities. Incredible perks include complimentary lake access at nearby beach, family board games, children's books, toys & a mini game table for ping-pong, air hockey, football & billiards!

Guest favourite

Home in Greenwood Lake

5 out of 5 average rating, 115 reviews

Time to escape to the lake!Hot-tub/1 hour from NYC

Lakefront, fully renovated and ready for guests to experience lake living at its best from the inside out. The modern gas fireplace and cozy sectional sofa make the living room the perfect place to perch over crisp autumn evenings. Or take a steaming soak in the backyard hot tub after a day of hiking or exploring all of neighboring Warwick’s wineries, breweries and local farms.With direct access to the lake from the property our location is ideal for kayaking. All within a 1 hour drive from NYC!

Home in Cornwall

4.82 out of 5 average rating, 93 reviews

State Forest Getaway

Enjoy our Mountain getaway for year round fun! There are lots of activities close by-Mohawk Ski Mountain, Indian Lake and historic Covered Bridges! Hike in the backyard, cool off in the creek or relax in front of the Wood-burning fireplace or get the whole family together for a fun BBQ on the outdoor deck. We have 4 comfortable bedrooms plus daybed room and 3 bathrooms and a fully equipped Chefs Kitchen. The living room is great for lounging and perfect a movie night watched on the projector

Guest favourite

Home in Lake Katrine

4.95 out of 5 average rating, 110 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favourite

Cabin in Kerhonkson

4.99 out of 5 average rating, 147 reviews

Lovely Catskill Cabin w/Piano and free firewood

When you truly want to get away from it all, come experience the wilderness of the Catskills. We're nestled next to 30k acres of the Sundown Wild Forest inside the 300k acres Catskill Park, 2 hrs from NYC. Enjoy any of the 3 fireplaces located in and around the cabin after your choice of 8 hiking trails you can take from our doorstep including the cascading pools of the secluded Vernooy Kill Falls. We are the closest Airbnb to the historic Vernooy Kills Falls and its 300-year-old ruins.

Serviced apartment in Beacon

4.84 out of 5 average rating, 102 reviews

Lovely 2 bed, 2 full bath. & private yard getaway

Bring the whole family to this super clean place with lots of room for fun. Private Yard ! kitchen/ dining room, living room, main bedroom w/king size bed & private bathroom, kid’s bedroom w/queen size bed & full bathroom across the room. This beautiful Airbnb has prime location. Across the street you will find the beautiful Madam Brett park w/waterfall and walking trail. Close to main street, train station, MT. Beacon also 8 min drive to Bannerman Castle and Dia Beacon Museum.

Home in Monticello

4.9 out of 5 average rating, 10 reviews

Luxurious & Newly Renovated Catskills Lakehouse

Come enjoy some winter fun in the Catskill Mountains! Grab your coat & gloves and head to the Catskills. Take the kids skiing or just make a snowman in the yard. Warm up with some hot cocoa or enjoy a winter BBQ on the deck. Try your luck at the casino or spend a day at the indoor water park. Your entire group will feel right at home in this renovated & comfortable house. Located right across from beautiful Sackett Lake, this is a great place for four season recreation.

Home in Middletown

4.89 out of 5 average rating, 122 reviews

Riverfront! Swim, Fish, Hot Tub & Game Barn.

Fish, Tube, Hot tub and Game room! All in one property! This exquisite riverfront home has 3 bedrooms and a sleeping loft. This magical property is 7 acres on the River. Bellayre beach 15 mins and Windham mountain biking 30 mins. Hike, s’mores by the fire, hang out in the 3 season game barn equipped with a pool table and darts, have a drink in the riverside hot tub. 5 mins to retro bowling and restaurants. NO FIRST TIME RENTERS ID VERIFIED/REVIEWED RENTERS ONLY.

Guest favourite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Guest favourite

Cabin in Accord

4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Just opened availability for Christmas and New Years Week! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” (ha!) and super chic Inness.

Guest favourite

Home in Bristol

4.92 out of 5 average rating, 160 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Guest favourite

Flat in Northampton

5 out of 5 average rating, 31 reviews

Downtown 2 BR 1.5 Bath Townhouse Retreat 3 beds

Conveniently located townhouse that is a short walk to restaurants and shops. Easy access to public transportation with a bus stop by the end of the street. Wi-Fi, a full kitchen, living room, 1/2 bath and laundry, on the first floor. The second floor has a shower, bedroom #1 has a queen bed and bedroom #2 has a queen and a twin. A/C units during summer months. Off street parking and self check in. Pack n play and toddler bed available upon request.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for The Berkshires family-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Guest favourite

Home in Saugerties

4.94 out of 5 average rating, 66 reviews

Perfect Family Winter Retreat•Close to Ski•Firepit

Guest favourite

Home in Athens

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Guest favourite

Home in Keene

4.96 out of 5 average rating, 49 reviews

Ultimate Family Vacation Home

Guest favourite

Home in Canajoharie

4.92 out of 5 average rating, 153 reviews

2 homes on large private mountain views getaway

Guest favourite

Home in Cohoes

5 out of 5 average rating, 117 reviews

Cheerful, quiet 3 bedroom home

Guest favourite

Home in Pine Plains

5 out of 5 average rating, 12 reviews

Stony Hill Haus in Pine Plains

Home in Putnam Valley

4.73 out of 5 average rating, 37 reviews

The Blue Lake House!

Guest favourite

Home in Northampton

5 out of 5 average rating, 34 reviews

Child-Friendly Northampton/Florence House!

Family-friendly apartment rentals

Flat in Hartford

4.8 out of 5 average rating, 114 reviews

Nice 2nd floor apt

Flat in West Brattleboro

4.76 out of 5 average rating, 131 reviews

Cute, Convenient with Big Backyard

Flat in Town of Rockingham

4.82 out of 5 average rating, 174 reviews

Apartment on Main Street

Guest favourite

Flat in Hudson

4.9 out of 5 average rating, 165 reviews

Private 1BR Apartment 1 Block from Warren St.

Guest favourite

Flat in Northampton

4.85 out of 5 average rating, 532 reviews

Parkside downtown cozy apartment

Flat in Newburgh

4.82 out of 5 average rating, 288 reviews

Unwind in a Bespoke Downtown Studio W Laundry

Flat in Middletown

4.88 out of 5 average rating, 290 reviews

3 bedroom near Wesleyan, downtown

Flat in Saratoga Springs

4.8 out of 5 average rating, 472 reviews

Fabulous apt downtown Saratoga N.Y.

Family-friendly apartment rentals

Guest favourite

Apartment in Windham

4.89 out of 5 average rating, 176 reviews

Cozy Mountain hideaway Windham, Hunter

Guest favourite

Apartment in Dover

4.82 out of 5 average rating, 102 reviews

Mount Snow Ski Chalet

Guest favourite

Apartment in Dover

4.99 out of 5 average rating, 112 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Guest favourite

Apartment in Dover

4.87 out of 5 average rating, 234 reviews

Mt Snow Ski In/Out at Seasons

Apartment in New Britain

4.82 out of 5 average rating, 120 reviews

New Britain "Joy of Small Space" Condo

Guest favourite

Apartment in Stratton

4.93 out of 5 average rating, 153 reviews

Updated Ski in/Ski out Stratton Condo!

Guest favourite

Apartment in Stratton

4.93 out of 5 average rating, 91 reviews

Great 2 bedroom condo at Stratton Mountain

Guest favourite

Apartment in Lanesville

4.97 out of 5 average rating, 608 reviews

Ski on/ Ski off Stylish Condo Hunter Mountain

Destinations to explore