Find Luxury Hotels in The Berkshires, MA

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Top The Berkshires Luxury Hotels

1862 Seasons on Main Bed and Breakfast
4.5 out of 5
47 Main Street, Stockbridge, MA
Treat yourself to a luxury stay at 1862 Seasons on Main Bed and Breakfast, where you'll find flat-screen TVs, plush bedding, and more. Deluxe amenities at this ...
5/5 Exceptional! (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, ..."

Reviewed on Aug 21, 2017

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1862 Seasons on Main Bed and Breakfast
33 Main
4 out of 5
33 Main Street, Lenox, MA
The price is $279 per night from Nov 8 to Nov 8
Be treated to luxurious lodging at 33 Main, where you'll find flat-screen TVs, plush bedding, and more.
5/5 Exceptional! (43 reviews)
"Great place to stay! Everyone is very friendly and the rooms are very clean and unique."

Reviewed on Sep 8, 2021

33 Main
Devonfield Inn B&B
4 out of 5
85 Stockbridge Rd., Lee, MA
The price is $309 per night from Nov 1 to Nov 1
Treat yourself to a luxury stay at Devonfield Inn B&B, where you'll find jetted bathtubs and a champagne service. Popular amenities include an outdoor pool, ...
4.9/5 Exceptional! (92 reviews)
"They thought of everything to make our stay comfortable - from plenty of places to charge our devices, luxury bathrobes, and many other amenities."

Reviewed on Oct 16, 2021

Devonfield Inn B&B
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The Barrington
4 out of 5
281 Main St., Level 3, Great Barrington, MA
Treat yourself to a luxury stay at The Barrington, where you'll find flat-screen TVs, a champagne service, and more. The lounge bar and snack bar are just some ...
4.8/5 Exceptional! (72 reviews)
"Delightfully welcoming"

Reviewed on Jun 15, 2021

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The Barrington
Lakehouse Inn
4 out of 5
615 Laurel St., Lee, MA
The price is $302 per night from Oct 21 to Oct 21
Discover some luxurious lodging at Lakehouse Inn, where you'll find flat-screen TVs, plush bedding, and more. Deluxe amenities at this bed & breakfast include ...
4.8/5 Exceptional! (64 reviews)
"What a lovely place! There were so many positives - great location on the lake and beautiful property with numerous places to sit outside, breakfast service was wonderful, the room was clean and had all the necessary amenities. The only downsides were that we could hear our neighbors walking around ..."

Reviewed on Aug 31, 2021

Lakehouse Inn
The Inn at Stockbridge
4 out of 5
30 East Street, Stockbridge, MA
Discover some luxurious lodging at The Inn at Stockbridge, where you'll find jetted bathtubs and premium bedding. Deluxe amenities at this bed & breakfast include ...
4.8/5 Exceptional! (84 reviews)
"Typical secondary large private house turned into an Inn with well preserved atmosphere. Spacious public rooms. Wonderful breakfast and friendly breakfast staff. Wine and cheese hour available early evening to relax after a busy day.Conveniently located ."

Reviewed on Jul 6, 2021

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The Inn at Stockbridge
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is $169 per night from Nov 2 to Nov 2
Indulge in a luxury vacation at The Williams Inn. Popular amenities include a restaurant, a fitness center, and a bar.
4.8/5 Exceptional! (123 reviews)
"Very comfortable and convenient!"

Reviewed on Oct 12, 2021

The Williams Inn
Stockbridge Country Inn
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
Pamper yourself with a luxury stay at Stockbridge Country Inn, where you'll find fireplaces, plush bedding, and more. Popular amenities include an outdoor pool, ...
4.6/5 Wonderful! (64 reviews)
"Our room was small, and filled with beautiful antiques. The breakfasts were awesome, Diane, our innkeeper, is a wonderful cook and full of information about Stockbridge history and things to do in the area. Greeting us in the morning helping us with our plans for the day, snd asking us how the day ..."

Reviewed on Sep 29, 2021

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Stockbridge Country Inn
Garden Gables Inn
4 out of 5
135 Main St, Lenox, MA
Be treated to luxurious lodging at Garden Gables Inn, where you'll find pillowtop beds, flat-screen TVs, and more. The outdoor pool, pool loungers, and terrace ...
4.6/5 Wonderful! (54 reviews)
"The Inn is in a prime location in Lenox. The breakfast is great! Lots of choices, and each breakfast is cooked to order. Nice area set up with beverages and snacks available 24/7. The arts season had concluded when we were there, and we plan to come back a little earlier to take advantage of that. ..."

Reviewed on Sep 27, 2021

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Garden Gables Inn
The Old Inn On The Green
4 out of 5
134 Hartsville-New Marlborough Rd, New Marlborough, Great Barrington, MA
The price is $260 per night from Nov 1 to Nov 1
Pamper yourself with a luxury stay at The Old Inn On The Green, where you'll find premium bedding and more. The outdoor pool, restaurant, and lounge bar are ...
4.4/5 Wonderful! (52 reviews)
"Back in time in facility, awesomely relaxing environment amd area."

Reviewed on Oct 18, 2021

The Old Inn On The Green
Hampton Terrace Inn
4 out of 5
91 Walker Street, Lenox, MA
The price is $319 per night from Oct 24 to Oct 24
Be treated to luxurious lodging at Hampton Terrace Inn, where you'll find flat-screen TVs, plush bedding, and more. Popular amenities include an outdoor tennis ...
4.4/5 Excellent! (41 reviews)
"My husband and I stayed at the Hampton Terrace Inn for 2 nights this September. We were looking for safe place to stay during these unfortunate COVID-19 pandemic times, with the option of separate lodging. We therefore stayed in one of the cottage suites which we found to be large, comfortable, quiet, ..."

Reviewed on Oct 3, 2021

Hampton Terrace Inn
Yankee Suites Extended Stay
4 out of 5
20 W Housatonic St., Pittsfield, MA
Enjoy a luxury stay at Yankee Suites Extended Stay, where you'll find premium channels and more.
4.4/5 Excellent! (163 reviews)
"Room was clean, roomy and comfortable. Full kitchen appliances and utensils made staying here convenient. Hotel is convenient to walking downtown. Briefly met the staff who was very friendly."

Reviewed on Oct 4, 2021

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Yankee Suites Extended Stay
Seven Hills Inn
4 out of 5
40 Plunkett Street, Lenox, MA
The price is $113 per night from Oct 28 to Oct 28
Treat yourself to a luxury vacation at Seven Hills Inn. Popular amenities include an outdoor pool, pool loungers, and a terrace.
3.9/5 Good! (215 reviews)
"Beautiful garden and common areas in the old house. Edith Wharton’s house with its beautiful garden is next door."

Reviewed on Oct 20, 2021

Seven Hills Inn
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Wheatleigh
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