Cheap Vacations in The Berkshires
- The Berkshires vacations
- 3-night The Berkshires vacations
- 4-night The Berkshires vacations
- 5-night The Berkshires vacations
- 6-7 night The Berkshires vacations
4-night The Berkshires vacations
Price found within the past 48 hours. Click for updated prices.
6-7 night The Berkshires vacations
Price found within the past 48 hours. Click for updated prices.
Flight deals to The Berkshires
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
MCO
Orlando
BDL
Hartford
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
SJU
San Juan
BDL
Hartford
$128 Roundtrip, found 10 hours ago
$128
Roundtrip
found 10 hours ago
ATL
Atlanta
BDL
Hartford
$169 Roundtrip, found 2 days ago
$169
Roundtrip
found 2 days ago
Top rated hotels for your The Berkshires vacation
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
28.42 mi from city center
$110 nightly
The price is $123 total per night
$123 total
Apr 20 - Apr 21
Total with taxes and fees
Located in Williamstown, Vacation Village in the Berkshires is a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Pool
Parking included
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Free Cancellation
36.78 mi from city center
$133 nightly
The price is $149 total per night
$149 total
May 14 - May 15
Total with taxes and fees
A stay at Hotel Downstreet, an Ascend Collection Hotel places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Pool
Hot Tub
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
17.93 mi from city center
$108 nightly
The price is $120 total per night
$120 total
May 19 - May 20
Total with taxes and fees
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's Marketplace.
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
- Motels in Great Barrington
- Lenox Hotels
- Romantic Getaways & Hotels in The Berkshires
- Hotels with Suites in Lee
- Hotels with a Gym in Lee
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- Hotels with Tennis Courts in Lee
- Business Hotels in Lenox
- Hotels with Childcare in Lenox
- Business Hotels in Stockbridge
- Hotels with Childcare in Lee
- 5 Star Hotels in The Berkshires
- Spa Resorts & in Lenox
- 3 Star Hotels in Sandisfield
- Lee Hotels
- Hotels with Free Parking in Great Barrington
- Hotels with Pools in Lee
- Extended Stay Hotels in Berkshire County
- Hotels with Airport Transfers in Stockbridge
- Spa Resorts & in Stockbridge
- Hotels near Pittsfield Municipal
- Hotels with Room Service in The Berkshires
- Sheffield Hotels
- Historic Hotels in The Berkshires
- 4 Star Hotels in Stockbridge
- Kid Friendly Hotels in Great Barrington
- Kid Friendly Hotels in The Berkshires
- 3 Star Hotels in The Berkshires
- Business Hotels in Lee
- Arcade Hotels in Great Barrington
- 4 Star Hotels in Great Barrington
- Romantic Getaways & Hotels in Lenox
- Cabin Rentals in Lee
- Spa Resorts & in Lee
- Hotels with Room Service in Stockbridge
- 5 Star Hotels in Lenox
- Hotels near National Shrine of the Divine Mercy
- Hotels with Balconies in Great Barrington
- Farmstay in Stockbridge
- Kid Friendly Hotels in Lenox
- Hotels on the Lake in Great Barrington
- Hotels with a Wedding Venue in Lenox
- Historic Hotels in Lee
- Pet Friendly Hotels in Great Barrington
- 5 Star Hotels in Lee
- Pittsfield Hotels
- Hotels with Tennis Courts in The Berkshires
- Green Hotels in The Berkshires
- Resorts in Lenox
- Hotels with Free Breakfast in The Berkshires
- Hotels with Air Conditioning in Stockbridge
- Hotels with Pools in Stockbridge
- 4 Star Hotels in The Berkshires
- Hotels with a Wedding Venue in The Berkshires
- Casino Resorts & in The Berkshires
- Hotels with Air Conditioning in Great Barrington
- Golf Resorts & in Lenox
- 4 Star Hotels in Lenox
- Pet Friendly Hotels in Lee
- 5 Star Hotels in Stockbridge
- Hotels with Shopping in Lee
- Romantic Getaways & Hotels in Lee
- Hotels with Room Service in Lenox
- Sherwood Forest Hotels
- Hotels with Bars in Great Barrington
- Beach Resorts & in Stockbridge
- Flights to The Berkshires
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- Flights to Great Barrington
^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 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.
