Explore 46 Luxury Hotels in The Berkshires

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Best Luxury Hotels in The Berkshires

Hotel On North

Hotel On North

297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Nov 29 to Nov 30
$125 total
Nov 29 - Nov 30
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self ...
9.6/10 Exceptional! (983 reviews)
"Staff very pleasant and accommodating."

Reviewed on Nov 10, 2026

Opens in a new windowHotel On North
Lantern House Motel

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

Opens in a new windowLantern House Motel
Sunset Inn

Sunset Inn

150 Housatonic Street Lee MA
$80 nightly
The price is $89 total per night from Nov 13 to Nov 14
$89 total
Nov 13 - Nov 14
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! (447 reviews)
"In town for a wedding. Perfect for this budget range. Room clean. Room temperature very adjustable. Shower pressure good. Starbucks right across the street."

Reviewed on Oct 21, 2026

Opens in a new windowSunset Inn
1896 House Country Inn & Motels

1896 House Country Inn & Motels

910 Cold Spring Road Williamstown MA
$99 nightly
The price is $111 total per night from Nov 12 to Nov 13
$111 total
Nov 12 - Nov 13
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, ...
6.8/10 (460 reviews)
"Checking in was a puzzle as no one was ever in the office. The key was in an envelope attached to the door. All of the 8 cars/guests were housed in rooms adjacent to each other which meant sounds could be heard through the walls! This was a problem re: sleeping!"

Reviewed on Nov 9, 2026

Opens in a new window1896 House Country Inn & Motels
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

26 Glendale Road, RR 183 Stockbridge MA
$389 nightly
The price is $434 total per night from Dec 12 to Dec 13
$434 total
Dec 12 - Dec 13
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 ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Orchards Hotel

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 ...
Opens in a new windowThe Orchards Hotel
The Yankee Inn

The Yankee Inn

461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Nov 15 to Nov 16
$126 total
Nov 15 - Nov 16
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. ...
Opens in a new windowThe Yankee Inn
Maple Terrace Motel

Maple Terrace Motel

555 Main St. Williamstown MA
$99 nightly
The price is $111 total per night from Nov 12 to Nov 13
$111 total
Nov 12 - Nov 13
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
Opens in a new windowMaple Terrace Motel
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More 4 star hotels in The Berkshires

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
1,073 hotels
Lowest Price
$89
Highest Price
$434
Popular hotels
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, The Orchards Hotel, Lantern House Motel, Hotel On North, 1896 House Country Inn & Motels, The Yankee Inn, Sunset Inn, Maple Terrace Motel

Popular Luxury Stays in The Berkshires

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