Explore 46 Luxury Hotels in The Berkshires

Name: 1896 House Country Inn & Motels
Price range: $117 total

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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

$149 nightly

$166 total

Mar 17 - Mar 18

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 ...

9.6/10 Exceptional! (832 reviews)

Great hotel. Great location. Rooms are very spacious. Staff is always friendly and helpful, especially Andrew at the front desk. A breakfast venue on premises would be a nice addition.

Reviewed on Mar 13, 2026

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

26 Glendale Road, RR 183 Stockbridge MA

$335 nightly

$374 total

Mar 29 - Mar 30

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! (110 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

$93 nightly

$103 total

Mar 23 - Mar 24

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 ...

9.2/10 Wonderful! (1,004 reviews)

Easy check-in; accommodating staff; clean room. Convenient but also quiet location.

Reviewed on Mar 12, 2026

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.

8.2/10 Very Good! (455 reviews)

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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Sunset Inn

150 Housatonic Street Lee MA

$95 nightly

$106 total

Mar 17 - Mar 18

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 ...

7.6/10 Good! (411 reviews)

Very comfortable bed and good hot shower. A good value for your money. Nice staff at front desk.

Reviewed on Jan 1, 2026

Wagon Wheel Inn

484 Pittsfield Rd Lenox MA

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)

We've been in worse, but not by much. It kept the wind out of our hair and the shower had plenty of hot water. That's about it

Reviewed on Oct 26, 2025

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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 ...

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1896 House Country Inn & Motels

910 Cold Spring Road Williamstown MA

$104 nightly

$117 total

Mar 18 - Mar 19

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, ...

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

More 4 star hotels in The Berkshires

Garden Gables Inn

135 Main St Lenox MA

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9.2/10 Wonderful! (57 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	1,113 hotels
Lowest Price	$103
Highest Price	$374
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 3 hours ago

Travelocity Verified Review

"yes"

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

Hotel Downstreet, an Ascend Collection Hotel

4 out of 5

Posted 10 days ago

Travelocity Verified Review

"For the price, is a good property. Convenient for our purposes. While not up to more modern standards, it is reasonably furnished. Location is a bit noisy due to traffic and trains. Limited decent food options."

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