Compare Winery Hotels in The Berkshires

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Check hotel availability in The Berkshires

23 Dec - 24 Dec
Tonight
Check prices in The Berkshires for tonight, 23 Dec - 24 Dec
24 Dec - 25 Dec
Tomorrow night
Check prices in The Berkshires for tomorrow night, 24 Dec - 25 Dec

Featured The Berkshires Winery Hotels

The Old Inn On The Green

The Old Inn On The Green

4 out of 5
134 Hartsville-New Marlborough Rd Great Barrington MA
The price is NZ$635 per night from 22 Jan to 23 Jan
NZ$635
22 Jan - 23 Jan 2026
includes taxes & fees
Stay at this inn in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Questing and New Marlborough Town Library are located ...
Opens in a new windowThe Old Inn On The Green
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
The price is NZ$221 per night from 5 Jan to 6 Jan
NZ$221
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking and daily housekeeping. Popular attractions Ebenezer II Gifts and Antiques and Hotchkiss ...
Opens in a new windowShaker Mill Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St Pittsfield MA
Fully refundable
The price is NZ$147 per night from 22 Jan to 23 Jan
NZ$147
22 Jan - 23 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowBest Western Plus Berkshire Hills Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

2 out of 5
42 Stockbridge Rd West Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is NZ$99 per night from 1 Jan to 2 Jan
NZ$99
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this motel in West Stockbridge. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the clean rooms in their reviews. Popular attractions ...
Opens in a new windowPleasant Valley Motel West Stockbridge
Chesapeake Inn of Lenox

Chesapeake Inn of Lenox

3 out of 5
210 West Street Lenox MA
Stay at this golf B&B in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen Morris House ...
Get rates
Opens in a new windowChesapeake Inn of Lenox
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
Stay at this motel in Great Barrington. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the helpful staff and the clean rooms in their ...
Get rates
Opens in a new windowMonument Mountain Motel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is NZ$260 per night from 7 Jan to 8 Jan
NZ$260
7 Jan - 8 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowFairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundableReserve now, pay when you stay
The price is NZ$146 per night from 19 Jan to 20 Jan
NZ$146
19 Jan - 20 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
Opens in a new windowQuality Inn
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 ...
Get rates
Opens in a new windowLantern House Motel
Don't see what you're looking for?
See all available properties in The Berkshires
View all properties
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.

Wineries with Accommodation

Search for hotels in The Berkshires on lastminute.com.au. You can easily find your hotels in The Berkshires using one of the methods below:

  • View our selection of featured hotels in The Berkshires
  • Use the map to find hotels in the The Berkshires neighbourhood you prefer
  • Use the filters to see hotels in a specific area of The Berkshires, select a specific theme, brand, or hotel class from basic (1 Star) to luxury hotels (5 Stars) in The Berkshires
  • Enter your travel dates to view the best deals on hotels in The Berkshires - while they last

The Berkshires hotels essential information

Accommodation
1,084 hotels
Lowest Price
NZ$99
Highest Price
NZ$635
Popular hotels
The Old Inn On The Green, Shaker Mill Inn, Best Western Plus Berkshire Hills Inn & Suites, Pleasant Valley Motel West Stockbridge, Chesapeake Inn of Lenox, Monument Mountain Motel, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Quality Inn, Lantern House Motel

Most recent The Berkshires hotel reviews

Vacation Village in the Berkshires
lastminute.co.nz Verified Review
5 / 5
My stay was great with no problems.
A verified traveller stayed at Vacation Village in the Berkshires
Posted 3 days ago
Vacation Village in the Berkshires

More ways to explore The Berkshires