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

$189 nightly

$211 total

Jul 27 - Jul 28

Total includes 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! (745 reviews)

"Staff were excellent and welcoming."

Reviewed on Jul 21, 2025

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd, Lenox, MA

Fully refundableReserve now, pay when you stay

$135 nightly

$151 total

Jul 30 - Jul 31

Total includes taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...

9/10 Wonderful! (1,003 reviews)

"Loved the outdoor flowers, friendly staff, balconies and water in lobby. Disliked weak shower and very noisy air conditioning. Also entrance to property needs better lighting, more than just the overhead sign."

Reviewed on Jul 22, 2025

Sunset Inn

150 Housatonic Street, Lee, MA

$108 nightly

$121 total

Aug 18 - Aug 19

Total includes 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! (392 reviews)

"I liked the convenience the safety of the hotel and the owner always asking if you needed anything and everything OK they did a good job"

Reviewed on Jul 13, 2025

Wagon Wheel Inn

484 Pittsfield Rd, PO Box 808, Lenox, MA

$69 nightly

$77 total

Jul 27 - Jul 28

Total includes 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! (611 reviews)

"Convenient location for my trip"

Reviewed on Jul 6, 2025

1896 House Country Inn & Motels

910 Cold Spring Road, Williamstown, MA

$99 nightly

$111 total

Jul 28 - Jul 29

Total includes 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 (345 reviews)

"Stayed here to hike around the area, and this motel was exactly what i wanted - pet friendly, affordable, simple, 10minutes from trailheads, and nice staff."

Reviewed on Jul 21, 2025

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

26 Glendale Road, RR 183, Stockbridge, MA

$468 nightly

$523 total

Jul 28 - Jul 29

Total includes 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 ...

"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer ..."

Reviewed on Jul 27, 2024

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

General Williams Estate House Lenox/Stockbridge

Stockbridge

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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	1,114 hotels
Lowest Price	$77
Highest Price	$523
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

5 out of 5

Posted 2 days ago

Travelocity Verified Review

"I like this place a lot and have stayed here many times over the years. Comfortable stay at a reasonable price at a convenient location in Pittsfield. "

A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG

Best Western Plus Berkshire Hills Inn & Suites

5 out of 5

Posted 6 days ago

Travelocity Verified Review

"Very friendly girl at the check-in who moved us (essentially upgraded us) to a suite after our initial room smelled of lingering cigarette smoke. She was very patient about my paranoia over the pilot light/flame in the room's fireplace. Great experience."

A verified traveler stayed at Best Western Plus Berkshire Hills Inn & Suites

The Yankee, Trademark Collection by Wyndham

5 out of 5

Posted 6 days ago

Travelocity Verified Review

" The friendliness and excellent service received from the staff. While we stayed at the Yankee, we expected a delivery from UPS and the staff at the registration ensured that we would be informed as soon as it arrived at the Yankee. There was a delay from UPS and it caused us some stress. The Yankee staff made sure we were kept informed of the delivery. Their concern was greatly appreciated. Thank you."

A verified traveler stayed at The Yankee, Trademark Collection by Wyndham