Deals on vacations and trips to Berkshire County
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Williamstown
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Berkshire County flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Schenectady Downtown
Seward Place
Save 100% on your flight
per person
Jul 9 - Jul 16
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
This hotel features an indoor pool, a gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A 24-hour business center, a terrace, and a garden are also on offer.
Hotel Brookmere & Arbor Spa
Save 100% on your flight
per person
Jul 9 - Jul 16
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Lodges At Cresthaven
Save 100% on your flight
per person
Jul 9 - Jul 16
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
A private beach, a 24-hour gym, and a restaurant are all featured at this smoke-free lodge. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.
Surfside On The Lake
per person
Jul 9 - Jul 16
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Albany (ALB)
This hotel features a private beach and 2 restaurants. Dine at the beachfront restaurant and relax with sun loungers. Enjoy the a rooftop terrace and perks like free self parking.
Top Berkshire County hotels deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
$136 nightly
The price is $152 total per night
$152 total
Jun 19 - Jun 20
Total includes taxes and fees
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $134 total per night
$134 total
Jun 17 - Jun 18
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $104 total per night
$104 total
Jun 22 - Jun 23
Total includes taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
$142 nightly
The price is $158 total per night
$158 total
Jun 10 - Jun 11
Total includes taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $113 total per night
$113 total
Jun 15 - Jun 16
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $133 total per night
$133 total
Jun 10 - Jun 11
Total includes taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. Express check-in is provided and the front desk is staffed around-the-clock.
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View all propertiesLowest 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.
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Where to stay in Berkshire County: Best areas for travelers
- Williamstown: This destination is heaven for art lovers, with no shortage of exciting places to see. Make a beeline for Sterling and Francine Clark Art Institute or at Williamstown Theatre Festival. If you're hungry for even more creativity, swing by The Clark Art Institute too. Consider comfortable stays like The Williams Inn, the Maple Terrace Motel and the Northside Motel.
- Lenox: Make sure to plan ahead so you can see all of this bustling destination. Tanglewood Music Center, Cranwell Golf Club and Shakespeare and Company ought to be first on your must-see list. If fantastic service and a cozy bed are your priorities, the Gateways Inn & Restaurant, the A Small Oasis in the Heart of Lenox and the Hampton Terrace Inn certainly won't disappoint.
- Great Barrington: Great Barrington is the perfect blend of urban life and nature. When it's time to escape the concrete jungle, make your way to Housatonic River Walk and Lake Buel. Questing is another great place to unplug and soak up some nature. Top-rated hotels here include the Country Cottage On Quiet Street!!, the Private, New Home on 10 Acres and the Days Inn by Wyndham Great Barrington.
- Pittsfield: With so many exciting things to see and do here, you'll have earned a relaxing night's sleep by the time the sun sets. The Holiday Inn & Suites Pittsfield-Berkshires, the Hotel On North or the Berkshire Inn are some of the best places to kick back and unwind after exploring Bousquet Ski Area and Hancock Shaker Village. Don't forget to make your way to Pittsfield State Forest, Colonial Theater, Berkshire Museum and Canoe Meadows Wildlife Sanctuary too.
- Lee: This excellent location combines the excitement of the city with the peacefulness of nature. Take a break from the busy streets at Wood's Pond or McLennan Reservation. Ashintully Gardens is one more favorite nature-based attraction. Welcoming hotels here include the Sunset Inn, the Pilgrim Inn and the Super 8 by Wyndham Lee/Berkshires/Outlet Area.
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