Explore 46 Luxury Hotels in The Berkshires

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Best Luxury Hotels in The Berkshires

Hotel On North

297 North Street Pittsfield MA

Fully refundableReserve now, pay when you stay

$133 nightly

$149 total

Dec 22 - Dec 23

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. There's ...

9.4/10 Exceptional! (798 reviews)

The room was very clean and spacious ! The staff were very friendly and helpful - the hotel itself had a great vibe complete with hardcover books in a little coffee nook - just perfect and fun !

Reviewed on Nov 10, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

26 Glendale Road, RR 183 Stockbridge MA

$414 nightly

$462 total

Dec 7 - Dec 8

Total with taxes and fees

A seasonal outdoor pool, free self parking, and laundry facilities are featured at this bed & breakfast. Guests will appreciate free perks like continental breakfast ...

9.2/10 Wonderful! (85 reviews)

It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

$64 nightly

$72 total

Dec 7 - Dec 8

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool ...

9/10 Wonderful! (1,007 reviews)

Room was clean and smelled nice, staff were friendly and helpful, hot tub was clean and not crowded!

Reviewed on Nov 16, 2025

Sunset Inn

150 Housatonic Street Lee MA

$86 nightly

$97 total

Dec 2 - Dec 3

Total with taxes and fees

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area and express check-out are also ...

7.4/10 Good! (410 reviews)

Very efficient

Reviewed on Sep 28, 2025

Wagon Wheel Inn

484 Pittsfield Rd Lenox MA

$69 nightly

$77 total

Nov 25 - Nov 26

Total with taxes and fees

A hot tub is featured at this motel, along with free self parking. WiFi in public areas is free. Express check-out is also provided.

7/10 Good! (641 reviews)

Good overall.

Reviewed on Oct 26, 2025

1896 House Country Inn & Motels

910 Cold Spring Road Williamstown MA

$113 nightly

$127 total

Dec 23 - Dec 24

Total with taxes and fees

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, ...

6.4/10 (364 reviews)

Vintage feel!

Reviewed on Oct 20, 2025

The Orchards Hotel

222 Adams Rd Williamstown MA

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the seasonal ...

A little dated. Restaurant shut down for renovations, disappointing

Reviewed on Mar 9, 2020

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Lantern House Motel

256 Stockbridge Road Great Barrington MA

A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and a picnic area are also provided.

Avoid staying here if you can.

The fact that they require a vaccine card should be mentioned in their Hotels.com profile. Luckily for me I had it in my car. I don't mind if some hotel owners want to require it, but it should be pretty clearly stated. The owner told me that I didn't need to use the air conditioner, that I should ...

Reviewed on Nov 22, 2021

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More 4 star hotels in The Berkshires

The Inn at Stockbridge

30 East Street Lee MA

$263 nightly

$294 total

Nov 25 - Nov 26

Total with taxes and fees

9.6/10 Exceptional! (98 reviews)

The Berkshires Luxury Hotels

Do you want to stay at an elegant 5 star hotel for your next getaway? Do you want to be pampered like royalty? When you're ready, the The Berkshires luxury hotels are the plush oasis you’ve been looking for.

Choose from the best luxury hotels in The Berkshires to make your stay as comfortable and memorable as possible. Deluxe amenities await you upon check-in—perks like a heated pool, luxurious spa, and 24-hour reception service will cater to your every need, no matter the hour. If you’re tired from the day’s activities and don’t feel like wandering around to look for a meal, sit down to dinner at one of the high-end restaurants on property or contact room service for a sophisticated dining experience in the comfort of your own suite. Getting to and from the airport will be an easy task as well because most of these fancy hotels offer a free shuttle service for easy transportation.

We want you to enjoy your next vacation in style and the top luxury resorts in The Berkshires will help you do just that. Browse Travelocity right now to find amazing deals on the best luxury hotels and 4 star hotels in The Berkshires, and plan your next opulent escape.

The Berkshires hotels essential information

Accommodation	1,091 hotels
Lowest Price	$72
Highest Price	$462
Popular hotels	The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Orchards Hotel, Lantern House Motel, Wagon Wheel Inn, Hotel On North, 1896 House Country Inn & Motels, The Yankee, Trademark Collection by Wyndham, Sunset Inn

Popular Luxury Stays in The Berkshires

Recent The Berkshires Hotel Reviews By Fellow Wanderers

Hotel Downstreet, an Ascend Collection Hotel

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"All the design elements are wonderful! I enjoyed the room and the beautiful view of the town and the mountains. So clean and so spacious!! The staff - not so much, but everything else great."

A verified traveler stayed at Hotel Downstreet, an Ascend Collection Hotel