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
The price is $211 total per night from Jul 21 to Jul 22
$211 total
Jul 21 - Jul 22
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! (742 reviews)
"The Hotel is lovely, clean, and has a minimal but thoughtful aesthetic. The bathroom and bedroom are huge, and the restaurant connected to the hotel is charming. The only drawback is the location. The town center is dilapidated and rundown, with many closed storefronts. I hope the town of Pittsfield ..."
Reviewed on Jun 28, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $179 total per night from Jul 13 to Jul 14
$179 total
Jul 13 - Jul 14
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! (1,002 reviews)
"Helpful staff. Restful adirondack chairs scattered around the property. Good breakfast options."
Reviewed on Jul 4, 2025
Sunset Inn
150 Housatonic Street, Lee, MA
$86 nightly
The price is $97 total per night from Jul 10 to Jul 11
$97 total
Jul 10 - Jul 11
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! (385 reviews)
Dated
"Dated but clean"
Reviewed on Jul 2, 2025
Wagon Wheel Inn
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night from Jul 6 to Jul 7
$77 total
Jul 6 - Jul 7
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! (606 reviews)
"Great location. Pleasant staff."
Reviewed on Oct 13, 2024
1896 House Country Inn & Motels
910 Cold Spring Road, Williamstown, MA
$99 nightly
The price is $111 total per night from Jul 7 to Jul 8
$111 total
Jul 7 - Jul 8
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 (337 reviews)
"We arrived after 7 pm and it turned out had reserved the room for Wednesday night instead of Monday night. A person associated with the restaurant which was closed on Monday, helped us. He called in to the staff and checked us into a room. Everything went so smoothly and it could have been last minute ..."
Reviewed on Jun 29, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
$497 nightly
The price is $555 total per night from Jul 14 to Jul 15
$555 total
Jul 14 - Jul 15
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
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
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
Hampton Terrace Inn
91 Walker Street, Lenox, MA
$351 nightly
The price is $392 total per night from Jul 7 to Jul 8
$392 total
Jul 7 - Jul 8
Total includes taxes and fees
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 | 1,097 hotels |
|---|---|
Lowest Price | $77 |
Highest Price | $555 |
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
The Yankee, Trademark Collection by Wyndham
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Helpful staff.
Restful adirondack chairs scattered around the property.
Good breakfast options. "
A verified traveler from barrington stayed at The Yankee, Trademark Collection by Wyndham
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