Compare Winery Hotels in The Berkshires

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

24 Feb - 25 Feb
Tonight
Check prices in The Berkshires for tonight, 24 Feb - 25 Feb
25 Feb - 26 Feb
Tomorrow night
Check prices in The Berkshires for tomorrow night, 25 Feb - 26 Feb

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, New Marlborough, Great Barrington, MA
The price is NZ$557 per night from 9 Mar to 10 Mar
NZ$557
includes taxes & fees
9 Mar - 10 Mar
Stay at this 4-star inn in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Questing and New Marlborough Town Library ...
The 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$201 per night from 26 Feb to 27 Feb
NZ$201
includes taxes & fees
26 Feb - 27 Feb
Stay at this B&B in West Stockbridge. Enjoy free breakfast, free parking, and daily housekeeping. Popular attractions Tanglewood Music Center and Ebenezer II ...
Shaker 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 refundableReserve now, pay when you stay
The price is NZ$195 per night from 25 Feb to 26 Feb
NZ$195
includes taxes & fees
25 Feb - 26 Feb
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best 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$116 per night from 28 Feb to 1 Mar
NZ$116
includes taxes & fees
28 Feb - 1 Mar
Stay at this motel in West Stockbridge. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the clean rooms in our reviews. Popular attractions ...
Pleasant Valley Motel West Stockbridge
Chesapeake Inn of Lenox

Chesapeake Inn of Lenox

3 out of 5
210 West Street, P.O. Box 1920, Lenox, MA
Stay at this 3-star golf B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Frelinghuysen Morris ...
Get rates
Chesapeake 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
The price is NZ$129 per night from 26 Feb to 27 Feb
NZ$129
includes taxes & fees
26 Feb - 27 Feb
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Monument 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$296 per night from 26 Feb to 27 Feb
NZ$296
includes taxes & fees
26 Feb - 27 Feb
Book a stay at this spa hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is NZ$147 per night from 9 Mar to 10 Mar
NZ$147
includes taxes & fees
9 Mar - 10 Mar
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Quality 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 WiFi, and free parking. Popular attractions Housatonic River and Lake Mansfield Park are located ...
Get rates
Lantern 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
1,038 hotels
Lowest Price
NZ$116
Highest Price
NZ$557
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
What a hidden gem! Very reasonably priced and much more comfortable than a typical hotel. Would highly recommend staying here!
A verified traveller stayed at Vacation Village in the Berkshires
Posted 1 day ago
Vacation Village in the Berkshires

More ways to explore The Berkshires