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Recommended hotels in Spencertown

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1001)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
The price is AED 343
AED 384 total
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus Berkshire Hills Inn & Suites

Bed & Breakfast in West Stockbridge

2.5 star property
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is AED 396
AED 435 total
includes taxes & fees
10 Dec - 11 Dec
Shaker Mill Inn

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1008)
"Great stay!"
United States
Ann
The price is AED 328
AED 366 total
includes taxes & fees
17 Dec - 18 Dec
The Yankee, Trademark Collection by Wyndham

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 337
AED 377 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pocketbook Hotel and Bath

2.0 star property
8.4 out of 10, Very Good, (10)
"The room was very nice, and the staff was great"
United States
Kienan
The price is AED 859
AED 1,137 total
includes taxes & fees
29 Dec - 30 Dec
Pocketbook Hotel and Bath

Element Lenox Berkshires

3.0 star property
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is AED 481
AED 537 total
includes taxes & fees
15 Dec - 16 Dec
Element Lenox Berkshires

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is AED 356
AED 398 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Motel in Great Barrington

2.5 star property
9.0 out of 10, Wonderful, (804)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel

Motel in Lenox

2.0 star property
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is AED 290
AED 324 total
includes taxes & fees
10 Dec - 11 Dec
Howard Johnson by Wyndham Lenox

Motel in Great Barrington

2.0 star property
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is AED 275
AED 308 total
includes taxes & fees
10 Dec - 11 Dec
Travelodge by Wyndham Great Barrington Berkshires

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1006)
"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 AED 372
AED 415 total
includes taxes & fees
18 Dec - 19 Dec
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Great Barrington

2.5 star property
8.4 out of 10, Very Good, (1000)
"Clean room, nice location "
United States
Devron
The price is AED 278
AED 310 total
includes taxes & fees
22 Dec - 23 Dec
Quality Inn Great Barrington

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is AED 379
AED 423 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Berkshires-Lenox

Lodge in Pittsfield

3.0 star property
9.0 out of 10, Wonderful, (784)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge

Guesthouse in Pittsfield

4.0 star property
8.6 out of 10, Excellent, (346)
"Very helpful staff, clean and spacious rooms. Has everything you need - well equipped."
United States
Lynn
The price is AED 328
AED 366 total
includes taxes & fees
10 Dec - 11 Dec
The Central Downtown Inn & Suites

Prospect Berkshires

3.0 star property
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 AED 955
AED 1,190 total
includes taxes & fees
10 Dec - 11 Dec
Prospect Berkshires

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
8.8 out of 10, Excellent, (706)
"Great hospitality "
United States
regina maria
The price is AED 375
AED 418 total
includes taxes & fees
15 Dec - 16 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Motel in Pittsfield

2.0 star property
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is AED 297
AED 332 total
includes taxes & fees
18 Dec - 19 Dec
Berkshire Inn

Spark by Hilton West Coxsackie

2.5 star property
7.6 out of 10, Good, (76)
"Great staff "
United States
John
The price is AED 320
AED 346 total
includes taxes & fees
21 Dec - 22 Dec
Spark by Hilton West Coxsackie

Motel in West Stockbridge

2.0 star property
6.8 out of 10, (1002)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is AED 193
AED 212 total
includes taxes & fees
1 Jan - 2 January 2026
Pleasant Valley Motel West Stockbridge
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 Spencertown Hotel Reviews