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Browse for The Berkshires Luxury Hotels from $50

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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
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5/5Exceptional! (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

1862 Seasons on Main Bed and Breakfast
Federal House Inn
3.5 out of 5
1560 Pleasant Street, Route 102, South Lee, MA
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4.8/5Exceptional! (178 reviews)

"Beautiful old house. Personable, helpful and accommodating staff. Wonderful homemade breakfast, wine hour and snacks. We had a great stay."…"

Reviewed on Dec 8, 2019

Federal House Inn
Hotel On North
3.5 out of 5
297 North Street, Pittsfield, MA
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4.7/5Exceptional! (266 reviews)

"Loved the unique decor of each room and nice touches not found elsewhere"…"

Reviewed on Feb 17, 2020

Hotel On North
Chambery Inn
3 out of 5
199 Main St, Lee, MA
Free CancellationReserve now, pay when you stay
The price is $90 per night
4.7/5Exceptional! (285 reviews)
Highly recommend

"Lovely getaway. Olga and Bob are the perfect host and hostess. Incredible history to this former school house.."…"

Reviewed on Feb 15, 2020

Chambery Inn
Maple Terrace Motel
2.5 out of 5
555 Main St., Williamstown, MA
Free CancellationReserve now, pay when you stay
The price is $84 per night
4.6/5Exceptional! (205 reviews)

"Had a terrific stay at the Maple Terrace - very tidy, clean room, bright, immaculate bath, and lovely chat with owners at complimentary breakfast. An excellent value! Thank you Ashwan and Ritu, I really hope to be back soon!"…"

Reviewed on Mar 17, 2020

Maple Terrace Motel
Stockbridge Country Inn
4.5 out of 5
26 Glendale Road, RR 183, Stockbridge, MA
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4.6/5Wonderful! (60 reviews)

"The house and grounds are lovely, well maintained and just a short drive away from Shakespeare and Co. Breakfast is delicious. A menu of items to choose from. The omelets are cooked to perfection! Diane is the perfect host. Very sweet and full of information and suggestions on what to do and where ..."…"

Reviewed on Jan 20, 2020

Stockbridge Country Inn
The Orchards Hotel
3.5 out of 5
222 Adams Rd, Williamstown, MA
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4.2/5Excellent! (447 reviews)

"A little dated. Restaurant shut down for renovations, disappointing"…"

Reviewed on Mar 9, 2020

The Orchards Hotel
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
Free Cancellation
The price is $85 per night
4.2/5Excellent! (641 reviews)

"Beautiful inn in a beautiful peaceful location. I highly recommend this place and it has a beautiful lake where you can rent a canoe for fun."…"

Reviewed on Jun 1, 2020

The Black Swan Lee - Lenox, Ascend Hotel Collection
Lantern House Motel
2.5 out of 5
256 Stockbridge Road, Great Barrington, MA
The price is $65 per night
4.2/5Very Good! (385 reviews)
Business Trip

"Room was nice and clean. No hair dryer or ironing board, but otherwise a very pleasant stay. Bathroom was clean, and the location was a 5-minute drive to downtown. I'd stay here again."…"

Reviewed on Mar 5, 2020

Lantern House Motel
Yankee Inn
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Free CancellationReserve now, pay when you stay
The price is $89 per night
4.1/5Very Good! (849 reviews)

"Well we enjoyed the pool we had it all to ourselves we also had a room with a Jacuzzi tub that was beautiful and clean and a fireplace and it was truly relaxing and romantic. Just what we needed"…"

Reviewed on Mar 23, 2020

Yankee Inn
Howard Johnson by Wyndham Lenox
2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Free CancellationReserve now, pay when you stay
The price is $57 per night
3.8/5Good! (270 reviews)

"It was very convenient, clean,so many light inside, warm room with quiet heating system and hot water was excellent ( I was there in January). I used microwave and it saved me money big time. But be aware no dishes and utilities there. Bring yours. Big food store across the road."…"

Reviewed on Jan 16, 2020

Howard Johnson by Wyndham Lenox
Travelodge by Wyndham Great Barrington Berkshires
2 out of 5
400 Stockbridge Rd, Great Barrington, MA
Free CancellationReserve now, pay when you stay
The price is $66 per night
3.8/5Good! (219 reviews)

"As good as it gets for a cheap, clean place to sleep."…"

Reviewed on Mar 3, 2020

Travelodge by Wyndham Great Barrington Berkshires
Super 8 by Wyndham Lee/Berkshires/Outlet Area
2 out of 5
170 Housatonic Street, Lee, MA
Free CancellationReserve now, pay when you stay
The price is $84 per night
3.7/5Good! (510 reviews)

"The staff was really nice. It’s an older property in a great location. The was clean the Dunkin’ Doughnuts is two door down and the dispensary is right next to that. It was quiet a good place to catch a good nights sleep."…"

Reviewed on Mar 12, 2020

Super 8 by Wyndham Lee/Berkshires/Outlet Area
Wagon Wheel Inn
2 out of 5
484 Pittsfield Rd, PO Box 808, Lenox, MA
The price is $69 per night
3.7/5Good! (344 reviews)

"This was in a good location. Cute old time feel to the property."…"

Reviewed on Jan 15, 2020

Wagon Wheel Inn
Lenox Inn
2 out of 5
525 Pittsfield Rd, Lenox, MA
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3.4/5Good! (530 reviews)

"Room was very hot, the people were very nice."…"

Reviewed on Jan 4, 2020

Lenox Inn
1896 House Country Inn
2.5 out of 5
910 Cold Spring Road, Williamstown, MA
The price is $89 per night
3.3/5 (143 reviews)

"Really enjoyed our night here. Everyone was friendly and the service was excellent. The rooms were spacious and lovely. The breakfast was the best! Such a quaint and beautiful place. We will be back!"…"

Reviewed on Mar 17, 2020

1896 House Country Inn
Sunset Inn
1.5 out of 5
150 Housatonic Street, Lee, MA
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3.3/5 (185 reviews)

"Location was good but room was old and small. It was very clean."…"

Reviewed on Oct 20, 2019

Sunset Inn
Econo Lodge Lee - Great Barrington
2 out of 5
980 Pleasant Street, Lee, MA
Free Cancellation
The price is $50 per night
3.1/5 (279 reviews)

"Really enjoyed balconies great price nice location"…"

Reviewed on Jan 17, 2020

Econo Lodge Lee - Great Barrington
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A weekend away keeps your worries at bay, so plan a vacation in The Berkshires and prepare to unwind. Intriguing monuments, delicious eats, and chances to take phenomenal pictures: these are just a few of the benefits of visiting The Berkshires. You'll treat yourself to decadent cuisine, get in line to see the coolest attractions, and snag seats to the most sought-after shows. Where else would you stay but in a luxury accommodation? Extravagant experiences are right up your alley, so book your elegant hotel in The Berkshires on Expedia.com right now and start your trip off on the right (well-dressed) foot.

5-Star Vacations in The Berkshires

It turns out plenty of folks love The Berkshires enough to call it home -- how is that for proof that The Berkshires is full of marvelous things to do? Whether you’re looking to spend your vacation dining on fine seasonal food or exploring museums in The Berkshires, you'll never be disappointed. The Berkshires is full of comfy hotels in addition to friendly locals, so it's no surprise that travelers come back. Book well in advance to ensure you snag a room!

Your luxury vacation begs for you to explore day spas, art, and local museums. When you're smart enough to book travel on Expedia.com, it's all at your fingertips. Thanks to our impressive room rates, your bucket list budget will always be intact. After a day of sightseeing, your luxury hotel is waiting with fine dining and incredible amenities. Before you drift off to dreamland, order a glass of wine to your room and revel in your successful day. The luxury accommodations in The Berkshires will lull you into a state of relaxation before you know it.

Luxury The Berkshires Hotels

It's that time; you're ready to get swept away in The Berkshires, and Expedia.com is here to make the process painless. Browse the wealth of real traveler reviews on dozens of hotels until you spot the perfect place to stay. 5-Star hotels treat you right, offering things like high end bath amenities and private kitchens. Some of the city's deluxe accommodations even feature upscale penthouses, while others have tennis courts or salt water pools. Use our mobile booking app to find and book a fabulous 5-star hotel in The Berkshires, and soon you'll be soaking up luxury in style!

Frequently asked questions

Are you looking for a luxury hotel for your The Berkshires vacation?
Travel to Albany, NY (ALB-Albany Intl.) Airport or Hartford, CT (BDL-Bradley Intl.) Airport, and then treat yourself to a stay at one of 46 The Berkshires luxury hotels. Known for its theater and skiing, The Berkshires also has some interesting things to see and do including Tanglewood Music Center and Jiminy Peak Mountain Resort, so you may want to take in the local sights during your visit.
What's the best luxury place to stay in The Berkshires?
1862 Seasons on Main Bed and Breakfast is a 4.5-star B&B with a restaurant and spa services, and it’s a popular choice for Expedia travelers looking for an elegant place to stay.
What's the seasonal weather like in The Berkshires?
The hottest months are usually July and August with an average temp of 77°F, while the coldest months are January and February with an average of 14°F. Average annual rainfall for The Berkshires is 45.38 inches.
What's there to see and do in The Berkshires?
Experience The Berkshires with a stop at Tanglewood Music Center, Jiminy Peak Mountain Resort, and Ski Butternut. If you have some spare time during your trip, you might want to check out Mass MoCA and October Mountain State Forest.
What's the best way to get around The Berkshires?
Take advantage of local transportation options that make it easy to see The Berkshires. To explore the surrounding area, hop aboard a train at Pittsfield Station or Pittsfield Intermodal Transportation Center.

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