Photo by Photo courtesy of Berkshire Visitors Bureau
Best Boutique Hotels in The Berkshires
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Boutique Hotels
Our top choices for The Berkshires boutique hotels
1. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
9.4 out of 10, Exceptional, (819 reviews)
"Nice view and location for fall color."
Md
The price is RM652
RM728 total
includes taxes & fees
8 Nov - 9 Nov
2. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
8.8 out of 10, Excellent, (852 reviews)
"Always a pleasurable stay. The rooms are clean, the amenities are appreciated, and the staff very attentive. Great location and as a single traveler I always feel safe staying here."
Cynthia
The price is RM337
RM376 total
includes taxes & fees
30 Nov - 1 Dec
3. Monument Mountain Motel
Monument Mountain MotelGreat Barrington
8.8 out of 10, Excellent, (937 reviews)
"Super clean and cozy and safe"
Andrea
The price is RM243
RM271 total
includes taxes & fees
3 Nov - 4 Nov
4. Quality Inn Great Barrington
Quality Inn Great BarringtonDowntown Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
"Our room was spotless and the staff was helpful and welcoming!"
Lynne
The price is RM307
RM343 total
includes taxes & fees
25 Nov - 26 Nov
5. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.2 out of 10, Wonderful, (1,004 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
Gustavo
The price is RM441
RM493 total
includes taxes & fees
2 Dec - 3 Dec
6. Berkshire Lake Lodge
Berkshire Lake LodgeLee
9.8 out of 10, Exceptional, (27 reviews)
"excellent lakeside view"
mike
The price is RM443
RM494 total
includes taxes & fees
6 Nov - 7 Nov
7. Wilder House Berkshires
Wilder House BerkshiresSheffield
9.8 out of 10, Exceptional, (72 reviews)
"Clean, cozy, and charming. The breakfast is delicious and all went smoothly."
Liliana
The price is RM665
RM743 total
includes taxes & fees
16 Nov - 17 Nov
8. East Rock Inn
East Rock InnGreat Barrington
9.6 out of 10, Exceptional, (58 reviews)
"East Rock was a nice, clean, and comfortable place to stay. Everything was great, and I enjoyed my stay."
Sharon
The price is RM493
RM551 total
includes taxes & fees
3 Dec - 4 Dec
9. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
Holiday Inn Club Vacations Oak n' Spruce Resort in the BerkshiresSouth Lee
9.2 out of 10, Wonderful, (1,001 reviews)
"Nice place to stay"
Michael
The price is RM475
RM610 total
includes taxes & fees
5 Nov - 6 Nov
10. The Yankee Inn
The Yankee InnLenox
9.2 out of 10, Wonderful, (1,008 reviews)
"The location was good for our trip."
Basil
The price is RM467
RM521 total
includes taxes & fees
20 Nov - 21 Nov
11. The Little Lion
The Little LionGreat Barrington
8.6 out of 10, Excellent, (637 reviews)
"A fine place for a quick overnight trip to the Berkshires."
David
The price is RM336
RM375 total
includes taxes & fees
9 Nov - 10 Nov
12. Courtyard by Marriott Lenox Berkshires
Courtyard by Marriott Lenox BerkshiresLenox
9.2 out of 10, Wonderful, (683 reviews)
"Great stay!"
Vandhana
The price is RM462
RM516 total
includes taxes & fees
29 Nov - 30 Nov
13. Prospect Berkshires
Prospect BerkshiresEgremont
10.0 out of 10, Exceptional, (51 reviews)
"Great experience!"
Sunny
The price is RM968
RM1,217 total
includes taxes & fees
30 Nov - 1 Dec
14. Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox SouthLee
8.6 out of 10, Excellent, (1,000 reviews)
"Perfect for a travel stop-over."
James
The price is RM334
RM373 total
includes taxes & fees
2 Dec - 3 Dec
15. Element by Marriott Lenox Berkshires
Element by Marriott Lenox BerkshiresLenox
9.6 out of 10, Exceptional, (51 reviews)
"Clean, spacious room
Accommodating staff especially Shawn and Jennifer at the front desk.
Very nice pool and gym
Definitely coming back"
Francis
The price is RM548
RM612 total
includes taxes & fees
8 Nov - 9 Nov
16. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
9.2 out of 10, Wonderful, (253 reviews)
"This a much better Holiday Inn than the one at Saugerties that we went one day before."
Yuguo
The price is RM418
RM467 total
includes taxes & fees
30 Nov - 1 Dec
17. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,252 reviews)
"Comfortable stay, well stocked kitchen and room."
Charline
The price is RM336
RM466 total
includes taxes & fees
8 Nov - 9 Nov
18. Hotel On North
Hotel On NorthPittsfield
9.6 out of 10, Exceptional, (975 reviews)
"Very nice hotel"
Philip
The price is RM471
RM526 total
includes taxes & fees
29 Nov - 30 Nov
19. Berkshires Untold
Berkshires UntoldLenox
9.0 out of 10, Wonderful, (1,060 reviews)
"A very good place to stay"
Madhavi R
The price is RM495
RM553 total
includes taxes & fees
29 Nov - 30 Nov
20. Shaker Mill Inn
Shaker Mill InnWest Stockbridge
9.6 out of 10, Exceptional, (483 reviews)
"Loved the location, fireplace and vibe"
Mahadeva
The price is RM454
RM499 total
includes taxes & fees
3 Nov - 4 Nov
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.
Top The Berkshires Hotel Reviews
Explore a world of travel with Expedia
- Apartments in Agawam
- Amherst Hotels
- Athol Hotels
- Belchertown Hotels
- Cabin Rentals in Berkshire County
- Caravan Parks in Berkshire County
- Castles in Berkshire County
- Bernardston Hotels
- Brimfield Hotels
- Charlemont Hotels
- Chicopee Hotels
- Easthampton Hotels
- Feeding Hills Hotels
- Greenfield Hotels
- Motels in Greenfield
- Hadley Hotels
- Lodges in Hampden County
- Hotels near Hancock Shaker Village
- Lee Hotels
- Longmeadow Hotels
- Monson Hotels
- Hotels near Mount Holyoke College
- Boutique Hotels in North Adams
- Northampton Hotels
- Northfield Hotels
- Palmer Hotels
- Rowe Hotels
- Savoy Hotels
- Sheffield Hotels
- Hotels near Six Flags New England
- Southwick Hotels
- Romantic Hotels in Springfield
- Springfield Hotels
- Sturbridge Hotels
- Hotels near Tanglewood Music Center
- Hotels with indoor pool in The Berkshires
- Luxury Hotels in The Berkshires
- Pet friendly Hotels in The Berkshires
- Relais & Chateaux Hotels in The Berkshires
- Budget Hotels in West Springfield
- Hotels with smoking rooms in West Springfield
- West Springfield Hotels
- Boutique Hotels in Western Massachusetts
- Westfield Hotels
- Flights to Amherst
- Flights to Belchertown
- Flights to Lee
- Flights to Northampton
- Flights to Sturbridge
- Flights to Western Massachusetts
- Flights from Westover Metropolitan
- Flights from Pittsfield Municipal
- Flights from Ludlow
- Flights from Shelburne Falls
- Flights from Lee
- Flights from Albuquerque (ABQ) to Pittsfield (PSF)
- Flights from Berlin (BER) to Westfield (BAF)
- Flights from Nashville (BNA) to Westfield (BAF)
- Flights from Buffalo (BUF) to Springfield (CEF)
- Flights from Charlotte (CLT) to Westfield (BAF)
- Flights from Columbus (CMH) to Springfield (CEF)
- Flights from Detroit (DTW) to Westfield (BAF)
- Flights from Freeport (FPO) to Westfield (BAF)
- Flights from Manta (MEC) to Westfield (BAF)
- Flights from New Orleans (MSY) to Springfield (CEF)
- Flights from Sanford (SFM) to Great Barrington (GBR)
- Visit Brimfield
- Charles H. Baldwin & Sons
- G. William Pitt House and Collection
- Green Acres Equestrian Center
- Visit Hampshire County
- Visit Hancock
- Housatonic River Walk
- Jacob's Pillow
- Kushi Institute
- Lee Premium Outlets
- Visit Lee
- Lenox Library
- Visit Monson
- Montague Bookmill
- Mount Greylock
- National Shrine of the Divine Mercy
- Otis Holidays
- Petersham Holidays
- Pittsfield Holidays
- Visit Pittsfield
- Pyramid Lake
- Springfield Holidays
- Stockbridge Holidays
- Studio 21 South
- Tanglewood Music Center
- Visit The Berkshires
- Visit Whately
- Visit Williamstown