Compare Luxury Hotels in The Berkshires

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Featured The Berkshires Luxury Hotels

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

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
The price is NZ$803 per night from 5 Jan to 6 Jan
NZ$803
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this luxury B&B in Stockbridge. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Chesterwood and Norman Rockwell Museum are located ...
Opens in a new windowThe Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Orchards Hotel

The Orchards Hotel

2.5 out of 5
222 Adams Rd Williamstown MA
Stay at this business-friendly hotel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Colonial Plaza and Linear Park are ...
Opens in a new windowThe Orchards Hotel
Lantern House Motel

Lantern House Motel

2.5 out of 5
256 Stockbridge Road Great Barrington MA
Stay at this motel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Opens in a new windowLantern House Motel
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Wagon Wheel Inn

Wagon Wheel Inn

2 out of 5
484 Pittsfield Rd Lenox MA
Stay at this motel in Lenox. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowWagon Wheel Inn
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$287 per night from 21 Jan to 22 Jan
NZ$287
21 Jan - 22 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowHotel On North
1896 House Country Inn & Motels

1896 House Country Inn & Motels

2.5 out of 5
910 Cold Spring Road Williamstown MA
Stay at this inn in Williamstown. Enjoy free parking, a business centre and a garden. Popular attractions Sheep Hill and Bullock Ledge Wildlife Management Area ...
Opens in a new window1896 House Country Inn & Motels
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$147 per night from 4 Jan to 5 Jan
NZ$147
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Sunset Inn

Sunset Inn

2 out of 5
150 Housatonic Street Lee MA
The price is NZ$175 per night from 24 Dec to 25 Dec
NZ$175
24 Dec - 25 Dec
includes taxes & fees
Stay at this motel in Lee. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular attractions Lee ...
Opens in a new windowSunset Inn
Maple Terrace Motel

Maple Terrace Motel

2.5 out of 5
555 Main St. Williamstown MA
Fully refundableReserve now, pay when you stay
The price is NZ$191 per night from 22 Jan to 23 Jan
NZ$191
22 Jan - 23 Jan 2026
includes taxes & fees
Stay at this business-friendly motel in Williamstown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowMaple Terrace Motel
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Luxury Hotels & Resorts in The Berkshires

What’s a holiday without a few upgrades here and there? Your busy life calls for an especially luxurious escape—even if you did just start thinking about it, and your annual leave starts tomorrow. But you don’t have to sacrifice A-list amenities and top-shelf touches just because you need to make a break for it; find luxury hotels in The Berkshires on lastminute.co.nz that’ll have you sinking into soft down pillows before Janice in accounting can catch up with you.

You may not be a celebrity, but there’s no reason you can’t be treated like one. Whether you require 2,000-thread-count sheets, perfectly veined Italian marble or down pillows made from the golden goose itself, luxury hotels near The Berkshires can deliver all that and more. Many of your accommodation options will offer oenophiles the chance to sip (or swill) prime wines, while fromage fanatics can chow down on fancy brie and camembert to their heart’s content. Need some sustenance to really soak up that wine? Now’s your chance to splurge on room service—it’s almost like having your own personal butler…almost.

Treat yo’self. Finding and booking our The Berkshires luxury hotels is a piece of cake. And speaking of cake—it should be delicious at your lavish lodging. So listen to your inner Paris Hilton and indulge yourself with the best of the best dining, service and comfort. With our discounts, you don’t have to be a regular at Tiffany & Co. to book the getaway of your dreams.

The Berkshires hotels essential information

Accommodation
1,084 hotels
Lowest Price
NZ$147
Highest Price
NZ$803
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, Maple Terrace Motel

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