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Check availability on Monterey Family Hotels

Our top choices for Monterey family-friendly hotels

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
"We have a dog traveling with us. It is really pet friendly. Love it!"
United States
Yan
The price is ¥17,858
¥19,948 total
includes taxes & fees
May 28 - May 29
Best Western Plus Berkshire Hills Inn & Suites

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (578 reviews)
  • cleanliness
    Escape with the kids to this quiet, comfortable motel where family stays come with free beds and cribs in immaculately clean rooms.
"Really nice little family business. Ty! "
United States
Raymond
The price is ¥11,751
¥13,125 total
includes taxes & fees
May 20 - May 21
Travelodge by Wyndham Great Barrington Berkshires

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"My family and I had a wonderful stay at Nicole's A-Frame."
United States
Loralee C.
The price is ¥22,844
¥58,769 total
includes taxes & fees
May 20 - May 21
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (93 reviews)
  • cleanliness
    Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is ¥18,472
¥20,633 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,010 reviews)
  • cleanliness
    Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
"We wojld considrr returning in warmer weather with the kids/ grandkids as the environment is family friendly."
United States
Melody
The price is ¥20,010
¥22,352 total
includes taxes & fees
May 17 - May 18
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (663 reviews)
  • cleanliness
    Family-friendly budget escape with free miniature golf and breakfast, minutes from Berkshire Botanical Garden.
"The room was a good value and provided a nice place for our family of 5 plus a small dog to lay our heads at night."
United States
Danny
The price is ¥9,988
¥11,156 total
includes taxes & fees
May 25 - May 26
Econo Lodge Lee - Great Barrington

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
9.2 out of 10, Wonderful, (892 reviews)
"I wish I had known about this place when my kids were young."
United States
JoAnn
The price is ¥20,089
¥25,513 total
includes taxes & fees
May 18 - May 19
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"I highly recommend for a group or family."
United States
deborah d.
The price is ¥62,876
¥110,440 total
includes taxes & fees
May 14 - May 15
Guesthouse Cabin vacation rentals in Berkshire County

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is ¥42,163
¥74,923 total
includes taxes & fees
May 20 - May 21
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (780 reviews)
  • cleanliness
    Families splash into fun at this Berkshires hotel with indoor pool, game arcade, and cozy rooms—all nestled near Ski Butternut.
"Staff are so friendly "
United States
Mary Cay
The price is ¥27,925
¥31,192 total
includes taxes & fees
May 17 - May 18
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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.

Choose what matters most at family-friendly hotels in Monterey

Top Monterey Hotel Reviews

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.

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