Cheap Vacations in The Berkshires
Flight deals to The Berkshires
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Aug 20 - Thu, Sep 5
ATL
Atlanta
BDL
Hartford
$68 Roundtrip, found 17 hours ago
$68
Roundtrip
found 17 hours ago
Thu, Oct 31 - Sun, Nov 3
TPA
Tampa
BDL
Hartford
$88 Roundtrip, found 2 days ago
$88
Roundtrip
found 2 days ago
Wed, Aug 21 - Wed, Aug 21
MCO
Orlando
BDL
Hartford
$91 Roundtrip, found 4 days ago
$91
Roundtrip
found 4 days ago
Top rated hotels for your The Berkshires vacation
Hotel Downstreet
40 Main St, North Adams, MA
Free Cancellation
Reserve now, pay when you stay
36.81 mi from city center
The price is $149 per night
$149
per night
Jun 23 - Jun 24
With a stay at Hotel Downstreet, you'll be centrally located in North Adams, within a 10-minute drive of Williams College and Western Gateway Heritage State Park.
Pool
Hot Tub
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
16.41 mi from city center
The price is $132 per night
$132
per night
Jun 24 - Jun 25
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Pet friendly
Parking included
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
17.41 mi from city center
The price is $125 per night
$125
per night
Jun 26 - Jun 27
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and Company.
Pool
Hot Tub
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.
Top Picks
Hotels
Hotels around Gillette StadiumHotels around Water WizzHotels in Downtown BostonWatertown Hotels with RestaurantsHotels around Wingaersheek BeachHotels around Salisbury Beach State ReservationHotels around West Dennis BeachCheap Hotels in MauiCheap Hotels in Cape CodHotels around Encore Boston HarborCheap Hotels in EverettCheap Hotels in WatertownCheap Hotels in NewtonHotels around Foxborough Country ClubHotels around MarketStreet LynnfieldCheap Hotels in LynnCheap Hotels in Martha's VineyardHotels around Salem HarborHotels around Tufts University
Flights
Recommended vacation destinations for you
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations
- Montreal Vacations
- Portland Vacations
- Houston Vacations
- St. Petersburg - Clearwater Vacations
- Savannah Vacations
- Fort Myers Vacations
- Tahoe City Vacations
- Reno Vacations
- Charleston Vacations
- Monterey Vacations
- Daytona Beach Vacations
- Charlotte Vacations
- Key West Vacations
- Naples Vacations
- Sedona Vacations
- Ocean City Vacations
- Sarasota Vacations
- Grand Canyon Vacations
^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.