Find Family Hotels in West Stockbridge, MA

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Check availability on West Stockbridge Family Hotels

Our top choices for West Stockbridge family-friendly hotels

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk
Best Western Plus Berkshire Hills Inn & Suites

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, (1001)
"Very friendly and good Breakfast."
United States
Jesse
The price is NT$2,382
NT$2,661 total
includes taxes & fees
Jan 4 - 2026/1/5
Best Western Plus Berkshire Hills Inn & Suites
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (12)
"New hotel very nice"
United States
joel
The price is NT$4,086
NT$4,565 total
includes taxes & fees
Dec 21 - Dec 22
Element Lenox Berkshires
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (988)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NT$2,932
NT$3,275 total
includes taxes & fees
Dec 19 - Dec 20
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
The price is NT$3,129
NT$3,495 total
includes taxes & fees
Jan 4 - 2026/1/5
The Black Swan Lee - Lenox, an Ascend Collection Hotel
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is NT$2,340
NT$2,613 total
includes taxes & fees
Dec 16 - Dec 17
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is NT$7,861
NT$9,826 total
includes taxes & fees
Dec 16 - Dec 17
Prospect Berkshires
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is NT$3,823
NT$4,270 total
includes taxes & fees
Jan 2 - 2026/1/3
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (804)
"Convenient location, very roomy, well equipped kitchen. "
United States
Carolyn
The price is NT$3,762
NT$4,812 total
includes taxes & fees
Dec 17 - Dec 18
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (758)
"Clean room, very courteous staff "
United States
Thomas
The price is NT$4,211
NT$4,704 total
includes taxes & fees
Dec 21 - Dec 22
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.
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Top West Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Your staff is very courteous and yes my room was spotless. "
FELICA 3-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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Frequently asked questions

What's West Stockbridge like for family-friendly vacations?
The budget-friendly destination of West Stockbridge is a good choice if you've been thinking about a trip with your kids. The lake views, wildlife, and forests are just a few things that make this an attractive family vacation spot. Take to the air and fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest airport, or Hudson, NY (HCC-Columbia County), which is located 17.8 mi (28.7 km) from the city center.
When's the best time to book a family-friendly vacation in West Stockbridge?
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 27°F. The snowiest months in West Stockbridge 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 West Stockbridge?
While you and your family are vacationing in West Stockbridge, you might want to visit some family-friendly attractions such as Charles H. Baldwin & Sons and Hotchkiss Mobile Studio. Make sure you have lots of time for activities like Ebenezer II Gifts and Antiques and Hoffman's Pottery.