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
$127 nightly
The price is $142 total per night from Nov 3 to Nov 4
$142 total
Nov 3 - Nov 4
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 ...
9.4/10 Exceptional! (775 reviews)
"Absolutely loved every part of my stay at Hotel North. Parking was so easy and safe. The Hotel is decorated so tastefully, the staff was so welcoming. When I stepped into my room, I felt I had walked into a soothing refuge. Your decorators knew just how to balance the aesthetics with furnishings, ..."
Reviewed on Sep 26, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $144 total per night from Oct 5 to Oct 6
$144 total
Oct 5 - Oct 6
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 ...
9/10 Wonderful! (1,014 reviews)
"I honestly just spent the night as part of a longer road-trip, but I found it quiet and comfortable, and the room was very clean when I arrived. Slept well, but unfortunately had to leave before breakfast."
Reviewed on Sep 30, 2025
Sunset Inn
150 Housatonic Street, Lee, MA
$100 nightly
The price is $112 total per night from Oct 6 to Oct 7
$112 total
Oct 6 - Oct 7
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 ...
7.4/10 Good! (407 reviews)
"Very efficient"
Reviewed on Sep 28, 2025
Wagon Wheel Inn
484 Pittsfield Rd, PO Box 808, Lenox, MA
$79 nightly
The price is $88 total per night from Oct 5 to Oct 6
$88 total
Oct 5 - Oct 6
Total with 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! (627 reviews)
"And I mean the David Lynch as a compliment."
Reviewed on Aug 14, 2025
1896 House Country Inn & Motels
910 Cold Spring Road, Williamstown, MA
$113 nightly
The price is $127 total per night from Oct 8 to Oct 9
$127 total
Oct 8 - Oct 9
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, ...
6.4/10 (361 reviews)
"Interesting cosy room, lovely seats on verandah, easy walk across bridge to Inn, easy tea and coffee maker."
Reviewed on Sep 27, 2025
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
$335 nightly
The price is $374 total per night from Oct 20 to Oct 21
$374 total
Oct 20 - Oct 21
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 ...
"Very expensive for a small room. My son and I could barely sleep in this remote quiet place. Staffs were very friendly."
Reviewed on Nov 2, 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
The Inn at Stockbridge
30 East Street, Lee, MA
$388 nightly
The price is $434 total per night from Nov 2 to Nov 3
$434 total
Nov 2 - Nov 3
Total with taxes and fees
9.6/10 Exceptional! (98 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 | 1,118 hotels |
|---|---|
Lowest Price | $88 |
Highest Price | $434 |
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 3 days ago
Travelocity Verified Review
"I honestly just spent the night as part of a longer road-trip, but I found it quiet and comfortable, and the room was very clean when I arrived. Slept well, but unfortunately had to leave before breakfast."
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
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