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Featured The Berkshires Luxury Hotels

See all 150 Hotels in The Berkshires
1862 Seasons on Main Bed and Breakfast

1862 Seasons on Main Bed and Breakfast

47 Main Street, Stockbridge
4.5 out of 5.0
5.0 out of 5 (19 reviews)
The best B & B we have ever stayed in!We have done B&B's for many years, but this experience beats them all. From the communication ahead of time by the lovely innkeeper Amanda, every detail was tended to. Small things like reading glasses in the dining room, umbrellas for loan at every door, use of the kitchen including silverware, ...
  Aug 21, 2017
Stockbridge Country Inn

Stockbridge Country Inn

26 Glendale Road, Stockbridge
5.0 out of 5.0
4.5 out of 5 (37 reviews)
Beautiful country homePersonal and warm welcome from our host. Comfortable and beautifully appointed room. Absolutely marvelous and sumptuous breakfast served on an elegantly set table. We will surely find an excuse to stay here again.
  Sep 11, 2017

$209

$209
The Orchards Hotel

The Orchards Hotel

222 Adams Rd, Williamstown
4.0 out of 5.0
4.4 out of 5 (285 reviews)
Pleasantly surprisedI took my teenage daughter to visit Williams College and there were not many upscale options. We chose Orchards based on good reviews and we were not disappointed! The room, bathroom and dressing area were palatial. The bed was super-comfortable and the linens were luxurious. We simply loved the ...
 Kathleen Mar 5, 2017

$139

$139
Federal House Inn

Federal House Inn

1560 Pleasant Street, South Lee
4.0 out of 5.0
4.8 out of 5 (119 reviews)
Best B&B in the BerkshiresFrom the moment we arrived to the day that we left, our stay at the Federal House Inn was truly exceptional. The attentiveness to detail, the delicious made-to-order breakfasts, the complimentary wine and social hour, the cleanliness of the rooms, and the tastefully decorated (yet comfortable) common ...
  Aug 23, 2017

$145

$145
Lantern House Motel

Lantern House Motel

256 Stockbridge Road, Great Barrington
3.0 out of 5.0
3.9 out of 5 (138 reviews)
Simple, safe stop along the way.Warm and friendly reception and beds were super comfy. Only thing was, I am a light sleeper and the heat/ac goes on and off all night, otherwise a nice experience!
  Dec 11, 2017

$60

$60
Wagon Wheel Inn

Wagon Wheel Inn

484 Pittsfield Rd, Lenox
2.0 out of 5.0
3.6 out of 5 (205 reviews)
Nothing fancy - good value - clean and comfortableStayed one night - was cheap, clean, and comfortable.
  Oct 18, 2014

$50

$50
Hotel On North

Hotel On North

297 North Street, Pittsfield
3.5 out of 5.0
4.8 out of 5 (129 reviews)
Amazing find in the BerkshiresThe Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than ...
 Steve Feb 28, 2016

$159

$159
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox
3.0 out of 5.0
3.8 out of 5 (487 reviews)
Nice place, nothing fancyGood experience, did not spend much time there. Clean well kept place, but not much to do if you are seeking activities
 les Jul 19, 2014

$80

$80
Sunset Inn

Sunset Inn

150 Housatonic Street, Lee
2.0 out of 5.0
3.1 out of 5 (149 reviews)
Nothing fancy--clean and comfortableFor a one-night stay, it was perfectly fine. Staff was courteous and let us check in a couple of hours early. If I had to stay in the area again, I'd go back there if it remains as inexpensive at the same quality of comfort and cleanliness.
 Susan Sep 8, 2015

$55

$55
Maple Terrace Motel

Maple Terrace Motel

555 Main St., Williamstown
3.0 out of 5.0
4.6 out of 5 (38 reviews)
Quiet and delightful, even on a very chilly weekend! The room was warm and cozy, the space just what we needed, and the staff friendly and helpful.
  Jan 2, 2018

$64

$64
Howard Johnson Express Inn - Lenox

Howard Johnson Express Inn - Lenox

462 Pittsfield Rd, Lenox
2.5 out of 5.0
3.5 out of 5 (567 reviews)
Decent; does the jobThis hotel is in a great location; nothing fancy but clean
 Robyn Jul 1, 2017

$55

$55
Travelodge Great Barrington Berkshires

Travelodge Great Barrington Berkshires

400 Stockbridge Rd, Great Barrington
2.5 out of 5.0
3.2 out of 5 (297 reviews)
Convenient to Butternut ski resortCheap and cheerful. Two comfortable beds, adequate bathroom, big TV, not noisy at night, AC/heater, can park right outside the room. Better breakfast than I had expected - with pastries, waffles, fruit, cereal, juice, coffee.
 Barry Jan 26, 2015

$63

$63
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

980 Pleasant Street, Lee
2.5 out of 5.0
3.2 out of 5 (169 reviews)
Not the Ritz, but great choice for value hotelIf you're like me and you're looking for a cheap place to sleep so you can hit the slopes early at nearby Catamount or Butternut, you've found a great place. It's not much of a hotel to look at, by any means, but the rate was hard to beat. We just wanted a clean room with a shower, which is what ...
  Feb 3, 2015

$44

$44
Chambery Inn

Chambery Inn

199 Main St, Lee
3.5 out of 5.0
4.7 out of 5 (141 reviews)
Exceeded my expectations"Exceeding expectations" is a cliche in customer service, but in this case it really happened. My room was spotless and featured an incredibly comfortable bed and a gas fireplace. I was greeted by a very friendly and helpful staff member who explained all the features of the room and gave me a hot-from-the-oven ...
 Brendan Mar 22, 2016

$121

$121
Black Swan Inn, an Ascend Collection Hotel

Black Swan Inn, an Ascend Collection Hotel

435 Laurel St, Lee
3.5 out of 5.0
4.1 out of 5 (377 reviews)
Fabulous view of Laurel LakeExtremely pleasant. Staff very helpful. Rooms are very comfortable, if not fancy. Breakfast is in need of major improvement--quantity does not insure quality.
  Aug 27, 2016

$76

$76
Super 8 Lee/Berkshires/Outlet Area

Super 8 Lee/Berkshires/Outlet Area

170 Housatonic Street, Lee
2.0 out of 5.0
3.6 out of 5 (278 reviews)
Convenient locationRoom was spacious and comfortable. Heating system was noisy, but when we turned it off, the room got too cold. The fridge was also noisy, and so we did turn it off since we didn't need it. Bath towels were very thin. Staff obligingly gave us extra ones. Room rate was good especially since we basically ...
 Ruth Dec 1, 2015

$63

$63
Lenox Inn

Lenox Inn

525 Pittsfield Rd, Lenox
2.0 out of 5.0
3.4 out of 5 (419 reviews)
Nothing FancyClean place, nothing fancy to talk about, and a cheap place to stay. A little dated.
  Jun 8, 2015

$43

$43
Monument Mountain Motel

Monument Mountain Motel

247 Stockbridge Rd, Great Barrington
3.0 out of 5.0
4.4 out of 5 (77 reviews)
It’s great hotel. Clean and quite.
  Jan 11, 2018

$60

$60
Crowne Plaza Pittsfield-Berkshires

Crowne Plaza Pittsfield-Berkshires

1 West St, Pittsfield
4.0 out of 5.0
3.6 out of 5 (449 reviews)
Perfect for a quick overnight trip. In the heart of downtown. Free parking
  Dec 29, 2017

$88

$88
The Porches Inn

The Porches Inn

231 River Street, North Adams
4.0 out of 5.0
4.6 out of 5 (95 reviews)
Luxury-like for low rateAesthetically pleasing. Night staff (Kim) exceptionally welcoming Loud generator noise but we treated it like white noise. Pack swim suit for pool and hot tub! Breakfast disappointing - busboy practically ran us down multiple times. We drove to Lenox for a proper breakfast!
 city girl Apr 12, 2015

$149

$149
Map

Recently booked Luxury Hotels in The Berkshires

Hotel On North
3.5 out of 5.0
Last booking: 32 minutes ago
Super 8 Lee/Berkshires/Outlet Area
2.0 out of 5.0
Last booking: 54 minutes ago
Vacation Village in the Berkshires
3.5 out of 5.0
Last booking: 3 hours ago
Berkshire Valley Inn
3.0 out of 5.0
Last booking: 3 hours ago
Garden Gables Inn
4.5 out of 5.0
Last booking: 8 hours ago
The Cornell Inn, Lenox
3.5 out of 5.0
Last booking: 10 hours ago
Monument Mountain Motel
3.0 out of 5.0
Last booking: 11 hours ago
The Egremont Village Inn
3.5 out of 5.0
Last booking: 11 hours ago
The Briarcliff Motel
2.5 out of 5.0
Last booking: 12 hours ago

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Luxury The Berkshires Hotels

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