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Hotels in The Berkshires

Choose from 987 The Berkshires Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
  • 28 min drive from Jiminy Peak Mountain Resort
The price is $121 per night from Nov 6 to Nov 7
$121
includes taxes & fees
Nov 6 - Nov 7
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (431 reviews)
"Cool people here. I mean they treat you with kindness."

Reviewed on Nov 2, 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
  • 46 min drive from Jiminy Peak Mountain Resort
The price is $200 per night from Dec 2 to Dec 3
$200
includes taxes & fees
Dec 2 - Dec 3
Stay at this 3.5-star spa hotel in Stockbridge. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
"The Autumn display, the charming setting The seating arrangement in the lobby Lended itself to conversation."

Reviewed on Oct 29, 2024

The Red Lion Inn
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
  • 25 min drive from Jiminy Peak Mountain Resort
The price is $94 per night from Nov 11 to Nov 12
$94
includes taxes & fees
Nov 11 - Nov 12
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,010 reviews)
Great Hotel! Would highly recommend!
"Great hotel at a good value."

Reviewed on Nov 1, 2024

The Yankee, Trademark Collection by Wyndham
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Black Swan Lee - Lenox, Ascend Hotel Collection
3 out of 5
435 Laurel St, Lee, MA
  • 39 min drive from Jiminy Peak Mountain Resort
The price is $115 per night from Nov 18 to Nov 19
$115
includes taxes & fees
Nov 18 - Nov 19
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
8.8/10 Excellent! (1,005 reviews)
"A wonderful visit. Beautiful site. Very clean. Just for a FYI. The restaurant on property Only serves Indian food. It looked very nice but we didn’t care for the menu options."

Reviewed on Oct 29, 2024

The Black Swan Lee - Lenox, Ascend Hotel Collection
Quality Inn
Quality Inn
2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
  • 1 hour drive from Jiminy Peak Mountain Resort
The price is $80 per night from Nov 18 to Nov 19
$80
includes taxes & fees
Nov 18 - Nov 19
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 ...
8/10 Very Good! (1,007 reviews)
"Great location, within a short walk to Greater Barrington. Room is clean and breakfast was good. A few areas could use some upkeep."

Reviewed on Oct 28, 2024

Quality Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 out of 5
190 Meadow Street, South Lee, MA
  • 47 min drive from Jiminy Peak Mountain Resort
The price is $166 per night from Nov 6 to Nov 7
$166
includes taxes & fees
Nov 6 - Nov 7
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (559 reviews)
"We had a one bedroom, and were surprised by how much room there was. Full kitchen, and a half bath downstairs. Close to a lot of the Berkshire's best attraction."

Reviewed on Oct 26, 2024

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
  • 13 min walk from Jiminy Peak Mountain Resort
The price is $195 per night from Nov 6 to Nov 7
$195
includes taxes & fees
Nov 6 - Nov 7
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a health club, and in-room massages. Our guests praise the helpful staff in our ...
8.6/10 Excellent! (1,738 reviews)
"Great price for a weekend gateway"

Reviewed on Nov 1, 2024

Vacation Village in the Berkshires
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
  • 25 min drive from Jiminy Peak Mountain Resort
The price is $144 per night from Nov 6 to Nov 7
$144
includes taxes & fees
Nov 6 - Nov 7
Stay at this hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our ...
8.6/10 Excellent! (1,006 reviews)
"Nice place to stay."

Reviewed on Oct 27, 2024

Hotel Downstreet
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3 out of 5
One West Street, Pittsfield, MA
  • 18 min drive from Jiminy Peak Mountain Resort
The price is $105 per night from Nov 15 to Nov 16
$105
includes taxes & fees
Nov 15 - Nov 16
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (666 reviews)
Nice stay
"Nice stay"

Reviewed on Oct 27, 2024

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Constance, The Whitlock, & The Dewey By The Lenox Collection
3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
  • 33 min drive from Jiminy Peak Mountain Resort
The price is $109 per night from Nov 7 to Nov 8
$109
includes taxes & fees
Nov 7 - Nov 8
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.4/10 Very Good! (338 reviews)
"This was a nice experience while traveling through the Berkshires. I would gladly stay here again."

Reviewed on Oct 28, 2024

The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
  • 26 min drive from Jiminy Peak Mountain Resort
The price is $245 per night from Dec 1 to Dec 2
$245
includes taxes & fees
Dec 1 - Dec 2
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ...
9.6/10 Exceptional! (363 reviews)
"Best location for stay in Williamstown. Was charged for full day upon arrival, although payment was already done through Expedia. Not clear why, took several conversations with staff to clear the charge."

Reviewed on Oct 29, 2024

The Williams Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
  • 57 min drive from Jiminy Peak Mountain Resort
The price is $132 per night from Nov 20 to Nov 21
$132
includes taxes & fees
Nov 20 - Nov 21
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (558 reviews)
"The holiday inn express was very clean and comfortable"

Reviewed on Nov 1, 2024

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in The Berkshires

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For you, intrepid voyager, Hotwire has a large selection of the best hotels in The Berkshires.

Choosing the right hotel in Massachusetts has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of The Berkshires’s 987 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $80. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% The Berkshires hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in The Berkshires. No matter your reason for visiting The Berkshires, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About The Berkshires hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in The Berkshires for as low as $80.

How many hotels are there in The Berkshires?

With over 987 hotels in The Berkshires, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $80.

How to find cheap car rentals in The Berkshires?

Finding a cheap car rental deal in The Berkshires is as easy as scoring cheap hotels in The Berkshires. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to The Berkshires now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to The Berkshires right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.