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Find Family Hotels in Monterey, MA

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Check availability on Monterey Family Hotels

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Top Monterey Family Hotels

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
8.0 out of 10, Very Good, (962)
Spacious suites accommodate families with comfort, while children splash in the heated indoor pool year-round. Located steps from Berkshire Museum, this hotel offers complimentary cribs and rollaway beds, alongside a restaurant serving delicious meals for hungry explorers.
The price is AED 328
AED 366 total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
  • Cribs/infant beds
8.6 out of 10, Excellent, (1001)
Family memories await at this thoughtful property, featuring spacious suites with premium TV channels and blackout drapes for restful evenings. Complimentary breakfast fuels adventures before heading to nearby Bousquet Ski Area, just a quick 5-minute drive away.
The price is AED 343
AED 384 total
includes taxes & fees
25 Nov - 26 Nov
Best Western Plus Berkshire Hills Inn & Suites
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
9.2 out of 10, Wonderful, (1006)
Splash into family fun at this hotel with dual pools, kid-friendly supervised swimming, and microwaves for quick snacks. Just a 3-minute drive from Bousquet Ski Area, the property combines mountain scenery with cozy rooms featuring cable TV and essential comforts.
The price is AED 273
AED 304 total
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
  • Cribs/infant beds provided
7.6 out of 10, Good, (560)
Family vacations shine at this peaceful Berkshire retreat offering complimentary cribs and rollaway beds for little ones. The refreshing pool delights with sunny and shaded areas, while the spotless accommodations and helpful staff ensure carefree comfort for travelers of all ages.
The price is AED 275
AED 308 total
includes taxes & fees
23 Nov - 24 Nov
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.8 out of 10, Exceptional, (11)
The price is AED 481
AED 537 total
includes taxes & fees
11 Dec - 12 Dec
Element Lenox Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
  • Cribs/infant beds provided
9.0 out of 10, Wonderful, (1001)
Playtime paradise awaits with free cribs, kayaking on the sparkling lake, and motor boating adventures. Children delight in fishing excursions, premium TV entertainment, and beachside fun while parents appreciate the lakefront setting and complimentary breakfast each morning.
The price is AED 390
AED 436 total
includes taxes & fees
12 Dec - 13 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
  • Cribs/infant beds provided
  • Indoor pool
9.4 out of 10, Exceptional, (60)
Vacation-ready accommodations feature premium TV channels and complimentary cribs for little travelers. Mornings begin with a free breakfast buffet, fueling adventures to nearby attractions. Spotlessly clean facilities and cheerful staff ensure a relaxing family retreat.
The price is AED 364
AED 407 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property amenity
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
  • Cribs/infant beds provided
  • Indoor pool
9.2 out of 10, Wonderful, (586)
Splash into adventure at this welcoming retreat, where the indoor swimming pool provides year-round fun while Netflix and premium channels entertain after outdoor explorations. Located just 6 minutes from Bousquet Ski Area, families enjoy complimentary cribs and parking.
The price is AED 433
AED 484 total
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Lenox Berkshires
Property amenity
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
  • Cribs/infant beds provided
  • Arcade/game room
9.4 out of 10, Exceptional, (755)
Vibrant game room captivates young adventurers while parents unwind in the soundproof accommodations or hot tub. After complimentary breakfast, families explore nearby skiing or Housatonic River Walk, returning to swim sessions in the pristine indoor pool.
The price is AED 555
AED 619 total
includes taxes & fees
26 Nov - 27 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Arcade
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
  • Cribs/infant beds provided
  • 2 outdoor pools
  • Arcade/game room
9.0 out of 10, Wonderful, (788)
The price is AED 391
AED 488 total
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.
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Top Monterey Hotel Reviews

Monument Mountain Motel

Monument Mountain Motel

10/10 Excellent
"This hotel was perfect for our one night stay. The room was very clean, bed was comfortable and the shower had good water pressure. The owners were very friendly. They had kuerig coffee available in the lobby, which was perfect to grab a cup of coffee to go."
Jeanne 1-night trip
Posted 19 hours ago
Monument Mountain Motel

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Frequently asked questions

What's Monterey like for family-friendly vacations?
The destination of Monterey is a great choice if you've been thinking about a vacation with your kids. The boating, parks, and swimming spots are just some of the things that make this the perfect spot for family trips. Arrange a flight into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 17.5 mi (28.1 km) from the city center.
When's the best time to book a family-friendly vacation in Monterey?
The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Monterey are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do with your family in Monterey?
While you are visiting Monterey, you might want to round up the kiddos and make time to see interesting attractions such as Bidwell House Museum and Ski Butternut. Make sure you have lots of time for activities like Otis Ridge and Jacob's Pillow.