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Check availability on The Berkshires Family-Friendly Hotels

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

Our top choices for The Berkshires family-friendly hotels

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

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 cosy rooms—all nestled near Ski Butternut.
₹15,395
₹17,196 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
A room with a foosball table, arcade games, and a large dartboard.
A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
₹11,212
₹14,397 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Club Vacations Oak 'n Spruce Resort
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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 Centre.
₹9,487
₹10,597 total
includes taxes & fees
1 Nov - 2 Nov
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 lodge with a large building and a dock by a lake, surrounded by forest.
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.
₹11,078
₹12,374 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
An outdoor seating area with Adirondack chairs and a fire feature.

5. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
₹14,470
₹16,163 total
includes taxes & fees
1 Nov - 2 Nov
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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
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 reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

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.
₹8,958
₹10,006 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel lobby with a reception desk, seating area with sofas and armchairs, a stone fireplace, and a television mounted on the wall.
A cozy living room with a stone fireplace, comfortable seating, and a welcoming sign.

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.
₹14,278
₹15,949 total
includes taxes & fees
18 Oct - 19 Oct
Jiminy Peak Mountain Resort
A garden with a decorative archway featuring large, smiling pumpkin sculptures.
A swimming pool with lounge chairs and a fence.
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
₹9,487
₹10,597 total
includes taxes & fees
1 Nov - 2 Nov
Maple Terrace 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.

9. 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 cots in immaculately clean rooms.
₹7,570
₹8,456 total
includes taxes & fees
18 Oct - 19 Oct
Travelodge by Wyndham Great Barrington Berkshires
An outdoor patio area with multiple chairs and tables, surrounded by lush greenery and trees.
A hotel room with a bed, a nightstand, a lamp, a window with curtains, and a painting on the wall.
A covered porch with beige siding, white railings, and a row of wooden benches.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

10. Cozy Corner Motel

Cozy Corner Motel
Williamstown
₹9,487
₹11,121 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Corner Motel
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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 snack bar with shelves of snacks and a refrigerated display.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
₹9,487
₹10,597 total
includes taxes & fees
1 Nov - 2 Nov
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 lodge with a large building and a dock by a lake, surrounded by forest.
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
₹11,078
₹12,374 total
includes taxes & fees
1 Nov - 2 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
₹11,212
₹14,397 total
includes taxes & fees
18 Oct - 19 Oct
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 hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
An outdoor seating area with Adirondack chairs and a fire feature.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
₹14,470
₹16,163 total
includes taxes & fees
1 Nov - 2 Nov
Element by Marriott Lenox Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
₹15,395
₹17,196 total
includes taxes & fees
1 Nov - 2 Nov
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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.
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 reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
Pittsfield
₹8,958
₹10,006 total
includes taxes & fees
1 Nov - 2 Nov
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
₹7,570
₹8,456 total
includes taxes & fees
18 Oct - 19 Oct
Travelodge by Wyndham Great Barrington Berkshires
An outdoor seating area with Adirondack chairs and potted plants.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

Cozy Corner Motel

Cozy Corner Motel
Williamstown
₹9,487
₹11,121 total
includes taxes & fees
7 Oct - 8 Oct
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 blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.
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.

Williamstown Motel

Williamstown Motel
Williamstown
₹7,215
₹8,059 total
includes taxes & fees
1 Nov - 2 Nov
Williamstown Motel
A hotel room with a bed, a desk, and two wall-mounted lamps.
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
₹6,272
₹7,006 total
includes taxes & fees
21 Oct - 22 Oct
Econo Lodge Lee - Great Barrington
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Family-friendly hotels with pools in The Berkshires

A building with a porch and multiple windows, surrounded by purple flowers.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A living room with a sofa, armchair, coffee table, and a patterned rug.

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
₹11,212
₹14,397 total
includes taxes & fees
18 Oct - 19 Oct
Holiday Inn Club Vacations Oak 'n Spruce Resort
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A snack bar with shelves of snacks and a refrigerated display.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
₹9,487
₹10,597 total
includes taxes & fees
1 Nov - 2 Nov
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 hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a wooden table and chairs.
An outdoor seating area with Adirondack chairs and a fire feature.

Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
₹14,470
₹16,163 total
includes taxes & fees
1 Nov - 2 Nov
Element by Marriott Lenox Berkshires
A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.
A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.
An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.
A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
₹15,395
₹17,196 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
An outdoor seating area with Adirondack chairs and potted plants.
A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.
A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.
A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

Cozy Corner Motel

Cozy Corner Motel
Williamstown
₹9,487
₹11,121 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Corner Motel
A garden with a swing set, a blue chair, and a flower bed.
A swimming pool with lounge chairs and a fence.
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
₹9,487
₹10,597 total
includes taxes & fees
1 Nov - 2 Nov
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 restaurant interior with wooden tables and chairs, hanging light fixtures, and large windows allowing natural light.
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
Hancock
₹14,278
₹15,949 total
includes taxes & fees
18 Oct - 19 Oct
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
Hotel On North

Hotel On North

10/10 Excellent
"A delightful find! Great room and staff. Excellent steak house next door."
molly 1-night trip
Posted 4 hours ago
Hotel On North
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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