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

$249 nightly

$278 total

Jul 15 - Jul 16

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! (873 reviews)

"The stay was wonderful! Great staff! We were heading to Tanglewood and they provided directions that were excellent. The room was beautiful, clean, and quiet."

Reviewed on Jul 5, 2026

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

26 Glendale Road, RR 183 Stockbridge MA

$358 nightly

$399 total

Jul 27 - Jul 28

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! (112 reviews)

"Our stay at The Inn was wonderful. Diane and staff could not have been more welcoming or helpful with great suggestions. Shopping and picnic supplies were spot on! Breakfast was delicious and more than plentiful. The pool was not available at this time, but what a beautiful setting. We’ll stay here ..."

Reviewed on Jun 30, 2026

The Yankee Inn

461 Pittsfield Rd Lenox MA

Fully refundableReserve now, pay when you stay

$151 nightly

$169 total

Jul 16 - Jul 17

Total with taxes and fees

This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...

9.2/10 Wonderful! (1,014 reviews)

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Reviewed on Jul 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

$110 nightly

$123 total

Jul 20 - Jul 21

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! (424 reviews)

"It was the only hotel that still had availability and I guess I know why. The only nice part was the pool. The room was from the 60s/70s complete with nonworking microwave and fridge. However, the real bad part was the poison. We saw a placed around in the bathroom and the subsequent dead mouse in ..."

Reviewed on Jul 12, 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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1896 House Country Inn & Motels

910 Cold Spring Road Williamstown MA

$110 nightly

$123 total

Jul 27 - Jul 28

Total with taxes and fees

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

6.6/10 (452 reviews)

"We were disappointed that this "Inn" is really an older motel, run together with another older motel across the highway and a converted barn/restaurant. We should have read the descriptions and reviews more carefully. On return, after checking the listing, it was perfectly clear. Note: If you want ..."

Reviewed on Jul 8, 2026

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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More 4 star hotels in The Berkshires

Hampton Terrace Inn

91 Walker Street Lenox MA

$315 nightly

$351 total

Jul 20 - Jul 21

Total with taxes and fees

9/10 Wonderful! (44 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	$123
Highest Price	$399
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 Inn, Sunset Inn