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Family friendly Hotels in The Berkshires, Massachusetts

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Check availability on The Berkshires Family friendly Hotels

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for The Berkshires family-friendly hotels

A room with multiple arcade games, including 'American Idol' and 'Toy Taxi'.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
P10,066
P11,243 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A room with a foosball table, arcade games, and a large dartboard.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
P7,331
P9,413 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Club Vacations Oak 'n Spruce Resort
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.

3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
P6,203
P6,929 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A dining area with large windows, wooden furniture, and a view of a lake.
A lakeside dock with kayaks and a covered boat ramp.

4. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
  • Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
P7,243
P8,090 total
includes taxes & fees
Nov 1 - Nov 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
An outdoor seating area with Adirondack chairs and a fire feature.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

5. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
P9,461
P10,568 total
includes taxes & fees
Nov 1 - Nov 2
Element by Marriott Lenox Berkshires
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

6. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
  • Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
P5,857
P6,542 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Berkshire Hills Inn & Suites
A wooden cabin with a porch and steps leading to a door, surrounded by snow.
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.
A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.
A hotel lobby with a reception desk, seating area with sofas and armchairs, a stone fireplace, and a television mounted on the wall.

7. Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
  • Family-friendly mountain resort with pools and skiing thrills for all ages in Jiminy Peak.
P9,336
P10,428 total
includes taxes & fees
Oct 18 - Oct 19
Jiminy Peak Mountain Resort
A garden with a decorative archway featuring large, smiling pumpkin sculptures.
A breakfast buffet setup with cereal, milk, juice, and pastries.
A house with a porch, snow-covered ground, and a Christmas tree with lights.
A garden with a swing set, a blue chair, and a flower bed.

8. Maple Terrace Motel

Maple Terrace Motel
Williamstown
P6,203
P6,929 total
includes taxes & fees
Nov 1 - Nov 2
Maple Terrace Motel
An outdoor patio area with multiple chairs and tables, surrounded by lush greenery and trees.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A covered porch with beige siding, white railings, and a row of wooden benches.
A hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.

9. Cozy Corner Motel

Cozy Corner Motel
Williamstown
P6,196
P7,263 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Corner Motel
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
A living room with a patterned carpet, two sofas, a dining table, and chairs.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.
A modern bathroom with a white sink, a toilet, and a bathtub.

10. Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
  • Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms.
P4,944
P5,522 total
includes taxes & fees
Oct 18 - Oct 19
Travelodge by Wyndham Great Barrington Berkshires
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Choose what matters most at family-friendly hotels in The Berkshires

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Family-friendly hotels with free breakfast in The Berkshires

An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A snack bar with shelves of snacks and a refrigerated display.

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
P6,203
P6,929 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A lakeside lodge with a dock, fishing rods, and outdoor seating.
A dining area with large windows, wooden furniture, and a view of a lake.
A lakeside dock with kayaks and a covered boat ramp.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
P7,243
P8,090 total
includes taxes & fees
Nov 1 - Nov 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
P7,331
P9,413 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Club Vacations Oak 'n Spruce Resort
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
An outdoor seating area with Adirondack chairs and a fire feature.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
P9,461
P10,568 total
includes taxes & fees
Nov 1 - Nov 2
Element by Marriott Lenox Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
P10,066
P11,243 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.
A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.
A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.
A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
P5,857
P6,542 total
includes taxes & fees
Nov 1 - Nov 2
Best Western Plus Berkshire Hills Inn & Suites
A hotel room with a large bed, a desk with a coffee maker, a chair, a TV, and a window with curtains.
A motel with a two-story structure, multiple rooms with red doors, and a central staircase.
A living room with a patterned carpet, two sofas, a dining table, and chairs.
A hotel room with a sofa, a wooden table, a lamp, a telephone, and a painting on the wall.

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
Great Barrington
P4,944
P5,522 total
includes taxes & fees
Oct 18 - Oct 19
Travelodge by Wyndham Great Barrington Berkshires
An outdoor seating area with Adirondack chairs and potted plants.
A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

Cozy Corner Motel

Cozy Corner Motel
Williamstown
P6,196
P7,263 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Corner Motel
A small, single-story building with a green roof and a white exterior. There are two large trees in front of the building, each with a flower pot on top. The surrounding area has grass, a few pumpkins, and a small garden with red flowers.
A kitchen with a fireplace, dining area, and a large window with curtains.
A living room with a sofa, chairs, a coffee table, and a rug. There is a kitchen area with a refrigerator and a water dispenser.
A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

Williamstown Motel

Williamstown Motel
Williamstown
P5,019
P5,606 total
includes taxes & fees
Nov 1 - Nov 2
Williamstown Motel
A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.
Front of property
A small kitchenette with a coffee maker, toaster, and cabinets. There is a red and green patterned floor and a plant on the left.
Balcony view

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
P4,101
P4,581 total
includes taxes & fees
Oct 22 - Oct 23
Econo Lodge Lee - Great Barrington
View all properties

Family-friendly hotels with pools in The Berkshires

A building with a porch and multiple windows, surrounded by purple flowers.
A café with a display case, a frozen food section, and a marketplace sign.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
P7,331
P9,413 total
includes taxes & fees
Oct 18 - Oct 19
Holiday Inn Club Vacations Oak 'n Spruce Resort
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A snack bar with shelves of snacks and a refrigerated display.

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
P6,203
P6,929 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.
An outdoor seating area with Adirondack chairs and a fire feature.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
P9,461
P10,568 total
includes taxes & fees
Nov 1 - Nov 2
Element by Marriott Lenox Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
P10,066
P11,243 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An outdoor seating area with Adirondack chairs and potted plants.
A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

Cozy Corner Motel

Cozy Corner Motel
Williamstown
P6,196
P7,263 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Corner Motel
A garden with a swing set, a blue chair, and a flower bed.
A breakfast buffet setup with cereal, milk, juice, and pastries.
A garden with a wooden pergola, potted plants, and a lawn with chairs.
A house with a porch, snow-covered ground, and a Christmas tree with lights.

Maple Terrace Motel

Maple Terrace Motel
Williamstown
P6,203
P6,929 total
includes taxes & fees
Nov 1 - Nov 2
Maple Terrace Motel
A resort with multiple buildings, a parking area, and a mountainous backdrop.
A wooden cabin with a porch and steps leading to a door, surrounded by snow.
A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.
A restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
P9,336
P10,428 total
includes taxes & fees
Oct 18 - Oct 19
Jiminy Peak Mountain Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place great price!"
James 1-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

8/10 Good
"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"
Theresa 2-night trip
Posted 3 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"So glad we stayed here! Our room was decorated like a 1940s Norman Rockwell painting, but had every modern comfort. We were in Stevens House, a half-block from the main inn - the shared living areas were like a home and our en-suite room was super nice. We had one dinner in the inn that was fancy, but we usually ate at other good restaurants & the patisserie within 1 block. Many fun shops, and a good laundromat also within 1 block."
Ruth 3-night trip
Posted 7 hours ago
The Red Lion Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"My impression s? It’s a quiet rural area, but I am impressed how quiet the motel was. Not all the time, but occasionally it get noisy. I also liked the area."
Casey A 4-night trip
Posted 22 hours ago
Best Western Plus Berkshire Hills Inn & Suites
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

8/10 Good
"Staff very pleasant and helpful. On site restaurant was good and reasonably priced. Room was large with a nice view. Breakfast, which is continental, seemed a bit skimpy. Plenty of parking and in a great central area with many restaurants."
Francesca 1-night trip
Posted 1 day ago
Hotel Downstreet, an Ascend Collection Hotel
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 3 days ago
Quality Inn Great Barrington

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