
Family-friendly holiday rentals in Pittsfield
Find and book unique family-friendly homes on Airbnb
Quick stats about holiday rentals that are family-friendly in Pittsfield

Total holiday rentals
Explore 120 holiday rentals in Pittsfield

Nightly prices starting at
Pittsfield holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 5,610 verified reviews to help you choose

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
120 of Pittsfield holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pittsfield rentals

4.9 Average rating
Pittsfield stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated family-friendly rentals in Pittsfield
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Downtown Apartment A
Centrally located in the Berkshires. Enjoy a beautiful day at Tanglewood, view the amazing art at Mass Moca or discover nature on one of the many hiking/biking trails the Berkshires has to offer. Located 5 mins from Bousquet and close to Jimmy Peak as well for anyone enjoying the snow! There are a variety of delicious restaurants to suit any appetite. Located in a quiet neighborhood, if your out & about all day or just looking to get away from the hustle & bustle of the city it's a perfect spot.
KitchenIndoor spacesCleanliness
4.93 out of 5 average rating, 117 reviews
Net Zero home with rustic Berkshire charm
Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!
FamilyIndoor spacesAccess
4.93 out of 5 average rating, 136 reviews
Fall Foliage Luxury Cabin & View Autumn Adventures
Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!
KitchenFamilyCheckout
4.97 out of 5 average rating, 109 reviews
Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!
FamilyKitchenSkiing
4.95 out of 5 average rating, 277 reviews
Berkshires Cottage by Lake. Year Round Adventures.
THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.
Indoor spacesFamilyGrill
4.95 out of 5 average rating, 320 reviews
Dancing Horse Lodge
Dancing Horse Lodge is located in the heart of the Berkshire Mountains in Pittsfield, MA, minutes from Tanglewood, Barrington Stage, Jacobs Pillow Ballet, Kripalu Yoga, Shakespeare and Co. and skiing at Bosquet and Jiminy Peak. It is a light and bright residence located on a 20-acre horse farm with nature views out of each window. It is surrounded by miles of woods, great for hiking and cross country skiing. Close to all amenities yet affords beautiful, quiet country living. Come and enjoy!
FamilyIndoor spacesLong stay
4.87 out of 5 average rating, 331 reviews
Berkshire 4 season home
The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.
FamilyIndoor spacesAccess
4.98 out of 5 average rating, 253 reviews
Brooksong, the perfect Berkshires getaway
Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!
FamilyKitchenTV
4.93 out of 5 average rating, 212 reviews
Cantabile life in the Berkshires
Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!
KitchenFamilyAir conditioning
4.95 out of 5 average rating, 240 reviews
Hidden Oasis in the Mountains by Evergreen Home
Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!
KitchenIndoor spacesCheck-in
4.97 out of 5 average rating, 157 reviews
The Hobbit House at June Farms
Watch June Farms on Amazon Prime Video! Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Highland cows, spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!
KitchenIndoor spacesRiver
4.97 out of 5 average rating, 256 reviews
Newly Renovated Red Door Annex
Private keypad entrance with parking. Large bedroom with a new Queen bed, full bathroom. There is a small table for dining and working, a small fridge, microwave, toaster oven, and pour-over coffee and tea in a nook (not a kitchen) outside the bedroom. Small outdoor sitting area. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas. 20 minutes to Lenox. The Annex is attached to the main house but is completely private.
Indoor spacesFamilyComfort
4.92 out of 5 average rating, 145 reviewsPopular amenities for Pittsfield family-friendly rentals
Family-friendly home rentals with a hot tub

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1
FamilyIndoor spacesHospitality
4.93 out of 5 average rating, 103 reviews
HOT TUB! Dog & Family Friendly in the Berkshires!
Indoor spacesKitchenGrill
4.94 out of 5 average rating, 135 reviews
Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna
FamilyKitchenDecor
4.97 out of 5 average rating, 185 reviews
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
FamilyKitchenAmenities
4.93 out of 5 average rating, 137 reviews
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
FamilyIndoor spacesTV
4.88 out of 5 average rating, 108 reviews
Jaw dropping mountain & lake views
Indoor spacesFamilyLayout
4.96 out of 5 average rating, 310 reviews
Berkshire family getaway at Jiminy Peak!
FamilyIndoor spacesView
4.92 out of 5 average rating, 115 reviews
Berkshire Mountain Top Chalet
FamilyIndoor spacesTV
4.93 out of 5 average rating, 193 reviewsFamily- and pet-friendly home rentals

King Bed | Stylish | Wi-Fi | *2m Ski Resort*
KitchenFamilyBathroom
4.91 out of 5 average rating, 178 reviews
Wildlife Lakeside Cottage; views/wildlife
KitchenFamilyBack garden
4.85 out of 5 average rating, 300 reviews
The old sawmill from 1771
Indoor spacesFamilyLayout
4.99 out of 5 average rating, 387 reviews
19th c. Barn in The Berkshires
KitchenIndoor spacesWifi
4.85 out of 5 average rating, 229 reviews
Netherwood - North Adams Guest House with Views
Indoor spacesFamilyCondition
5.0 out of 5 average rating, 337 reviews
The Beer Diviner Brewery Apartment
Indoor spacesKitchenHospitality
4.9 out of 5 average rating, 235 reviews
Cozy lakehouse
FamilyKitchenBathroom
5.0 out of 5 average rating, 119 reviews
Sweet Victorian in Housatonic
KitchenFamilyGetting around
4.95 out of 5 average rating, 177 reviewsFamily-friendly home rentals with a pool

Cozy cottage with pool, walking distance to lake
KitchenFamilyParks
4.95 out of 5 average rating, 171 reviews
Beautiful Jiminy Peak Townhome Family Friendly
KitchenFamilyHeating
4.83 out of 5 average rating, 109 reviews
Berkshire Vacation Home in Lee
Indoor spacesFamilyGrill
4.93 out of 5 average rating, 106 reviews
Luxe Retreat+Sauna+HotTub & Swimming on 12 acres
Indoor spacesKitchenGetting around
4.98 out of 5 average rating, 135 reviews
Lake House close to Skiing & Indoor Hot Tub
Indoor spacesKitchenAccuracy
4.96 out of 5 average rating, 113 reviews
Hollywood Bungalow in the Berkshires #C0191633410
FamilyKitchenAir conditioning
4.9 out of 5 average rating, 242 reviews
Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse
KitchenIndoor spacesHiking
4.91 out of 5 average rating, 184 reviews
Hudson getaway w/ hot tub+ plunge pool on 20 acres
KitchenFamilyHospitality
4.94 out of 5 average rating, 198 reviewsWhen is the best time to visit Pittsfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $278 SGD | $254 SGD | $245 SGD | $290 SGD | $310 SGD | $306 SGD | $328 SGD | $315 SGD | $287 SGD | $299 SGD | $278 SGD | $251 SGD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Destinations to explore
- New York Holiday rentals
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- Rentals with pools Pittsfield
- Waterfront rentals Pittsfield
- House rentals Pittsfield
- Rentals with a hot tub Pittsfield
- Rentals with lake access Pittsfield
- Flat rentals Pittsfield
- Pet-friendly rentals Pittsfield
- Family-friendly rentals Berkshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Stratton Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Taconic State Park
- Thacher State Park
- Kent Falls State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Hildene, The Lincoln Family Home
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Ski Sundown
- Rensselaer Polytechnic Institute
- Naumkeag
- University of Massachusetts Amherst
- MVP Arena
- Poets' Walk Park
- New York State Museum





