The Berkshires Luxury Hotels
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured The Berkshires Luxury Hotels

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183, Stockbridge, MA
$425 nightly
The price is $475 total per night
$475 total
Aug 11 - Aug 12
Total includes taxes and fees
Guests of The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood enjoy access to free WiFi in public areas, conference space, and a seasonal outdoor pool. Free parking is included with your stay. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this luxury bed & breakfast include coffee/tea in a common area, a computer station, and a library.
Pool
Breakfast included

The Orchards Hotel
222 Adams Rd, Williamstown, MA
Guests of The Orchards Hotel enjoy a gym, free WiFi in public areas, and meeting rooms. You can put free parking to good use if you drive. The 24-hour front desk has staff standing by to help with concierge services, luggage storage, and securing valuables. Additional amenities include conference space, a business center, and a seasonal outdoor pool.
Pool
Breakfast included

Lantern House Motel
256 Stockbridge Road, Great Barrington, MA
Guests of Lantern House Motel enjoy free WiFi in public areas, a seasonal outdoor pool, and a picnic area. If you decide to drive, there's free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. This motel also has a garden.
Pool
Breakfast included

Wagon Wheel Inn
484 Pittsfield Rd, PO Box 808, Lenox, MA
$69 nightly
The price is $77 total per night
$77 total
Jul 30 - Jul 31
Total includes taxes and fees
Guests of Wagon Wheel Inn enjoy free WiFi in public areas, a hot tub, and coffee in a common area. Free parking is available if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours. This motel also has express check-out.
Hot Tub
Parking included

Hotel On North
297 North Street, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$189 nightly
The price is $211 total per night
$211 total
Aug 3 - Aug 4
Total includes taxes and fees
Hotel On North features free WiFi in public areas, meeting rooms, and a business center. There's free parking if you drive. Front-desk staff can answer questions 24/7, and assist with concierge services, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include coffee/tea in a common area, an ATM, and a banquet hall.
Pet friendly
Parking included

1896 House Country Inn & Motels
910 Cold Spring Road, Williamstown, MA
$119 nightly
The price is $133 total per night
$133 total
Jul 30 - Jul 31
Total includes taxes and fees
1896 House Country Inn & Motels features free WiFi in public areas, conference space, and a business center. Free parking is included with your stay. Staff members are on hand to provide tour or ticket assistance and luggage storage. Additional amenities include a computer station, a terrace, and a garden.
Pet friendly
Parking included

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $178 total per night
$178 total
Jul 30 - Jul 31
Total includes taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub

Sunset Inn
150 Housatonic Street, Lee, MA
$110 nightly
The price is $123 total per night
$123 total
Aug 18 - Aug 19
Total includes taxes and fees
Guests of Sunset Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and express check-out. If you drive, take advantage of free parking. Front-desk staff are standing by 24/7 to assist with any requests. This motel also has a picnic area.
Pool
Parking included

Maple Terrace Motel
555 Main St., Williamstown, MA
$125 nightly
The price is $140 total per night
$140 total
Aug 17 - Aug 18
Total includes taxes and fees
Maple Terrace Motel features free WiFi in public areas, a seasonal outdoor pool, and coffee in a common area. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with concierge services, and offer advice about sights and eateries nearby. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a microwave in a common area, express check-out, and free newspapers.
Pool
Breakfast included

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $111 total per night
$111 total
Jul 30 - Jul 31
Total includes taxes and fees
Howard Johnson by Wyndham Lenox features an outdoor pool, free WiFi in public areas, and coffee in a common area. There's free parking if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include express check-out, a vending machine, and a garden.
Pool
Parking included

Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $99 total per night
$99 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests staying at Travelodge by Wyndham Great Barrington Berkshires enjoy free WiFi in public areas, laundry facilities, and a garden. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with dry cleaning/laundry and securing valuables. Additional amenities include a picnic area, a vending machine, and barbecue grills.
Pet friendly
Parking included

Econo Lodge Lee - Great Barrington
980 Pleasant Street, Lee, MA
Free Cancellation
Reserve now, pay when you stay
$64 nightly
The price is $71 total per night
$71 total
Aug 11 - Aug 12
Total includes taxes and fees
Econo Lodge Lee - Great Barrington features free WiFi in public areas and a vending machine. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area.
Breakfast included
Pet friendly

Chambery Inn
199 Main St, Lee, MA
$250 nightly
The price is $279 total per night
$279 total
Jul 30 - Jul 31
Total includes taxes and fees
Guests of Chambery Inn enjoy free WiFi in public areas, a hot tub, and spa services. A stay here includes free parking. Front-desk staff can assist with securing valuables and luggage storage. Additional amenities include express check-in, express check-out, and free newspapers.
Hot Tub
Spa

The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
$195 nightly
The price is $217 total per night
$217 total
Aug 6 - Aug 7
Total includes taxes and fees
Guests of The Black Swan Lee - Lenox, Ascend Hotel Collection enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly

Quality Inn
170 Housatonic Street, Lee, MA
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $139 total per night
$139 total
Aug 26 - Aug 27
Total includes taxes and fees
At Quality Inn, guests have access to free WiFi in public areas, express check-in, and express check-out. Onsite parking is offered for a fee. The front desk is staffed 24/7 to help with tours or tickets, and answer any questions about the accommodations. This hotel also has free newspapers.
Breakfast included
Free WiFi
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.
The Berkshires hotels essential information
Accommodation | 1,113 hotels |
---|---|
Lowest Price | $71 |
Highest Price | $475 |
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, Howard Johnson by Wyndham Lenox, Travelodge by Wyndham Great Barrington Berkshires, Econo Lodge Lee - Great Barrington, Chambery Inn, The Black Swan Lee - Lenox, Ascend Hotel Collection, Quality Inn |
Recent Luxury Hotels Reviews

Hotel Downstreet, Ascend Hotel Collection
5/5 Excellent
"Loved the staff and art centric area. "
A verified traveler stayed at Hotel Downstreet, Ascend Hotel Collection
Posted 2 days ago
Other Luxury Hotels
Areas Of The Berkshires
Hotels Near
Hotel Themes
Flights To
Other Popular Accommodations
Top Trending
Hotels
- Cape Cod Romantic Getaways & Hotels
- Central Massachusetts Luxury Hotels
- Cape Cod Pet Friendly Hotels
- North Shore Hotels with Hot Tubs
- Martha's Vineyard Hotel Deals
- Cape Cod Oceanfront Hotels
- Cape Cod Kid Friendly Hotels
- Cape Cod Hotels with an Indoor Pool
- Cape Cod Hotels with Balconies
- Nantucket Island Hotel Deals
- Cape Cod Beach Resorts & Hotels
- Cape Cod All Inclusive Resorts & Hotels
- Cape Cod Spa Resorts & Hotels
- Western Massachusetts Romantic Getaways & Hotels
- Cape Cod Hotel Deals
- Cape Cod Cheap Hotels
- Cape Cod Hotels with Hot Tubs
- Western Massachusetts Hotels with Hot Tubs
- Cape Cod Casino Resorts & Hotels
- Cape Cod Hotels with Kitchenettes
- Cape Cod Waterpark Hotels & Resorts
Flights