Cheap Vacations in The Berkshires

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3-night The Berkshires vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
Price was $449, price is now $376 per person
$376
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,061, price is now $669 per person
$669
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Gedney Farm

Gedney Farm

3.5 out of 5
Price was $682, price is now $474 per person
$474
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $771, price is now $558 per person
$558
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater Sunny Pond

3 out of 5
Save 100% on your flight
Price was $5,467, price is now $4,050 per person
$4,050
per person
Jan 30 - Feb 2
found 12 hours ago
Roundtrip flight included
Harlingen (HRL) to Albany (ALB)
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Price was $818, price is now $624 per person
$624
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $557, price is now $445 per person
$445
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
Price was $685, price is now $568 per person
$568
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $474, price is now $397 per person
$397
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)
Secluded Lux Mansion Pool Home With Amazing Views

Secluded Lux Mansion Pool Home With Amazing Views

2 out of 5
Save 100% on your flight
Price was $2,121, price is now $1,789 per person
$1,789
per person
Jan 30 - Feb 2
found 12 hours ago
Roundtrip flight included
Harlingen (HRL) to Albany (ALB)
Secluded Berkshires Estate + Private Pond/pool,theater, Gym Sunny Pond

Secluded Berkshires Estate + Private Pond/pool,theater, Gym Sunny Pond

3 out of 5
Save 100% on your flight
Price was $5,031, price is now $4,259 per person
$4,259
per person
Jan 30 - Feb 2
found 12 hours ago
Roundtrip flight included
Harlingen (HRL) to Albany (ALB)
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
Price was $793, price is now $675 per person
$675
per person
Jan 15 - Jan 18
found 21 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Albany (ALB)

4-night The Berkshires vacations

Price found within the past 48 hours. Click for updated prices.
Gedney Farm

Gedney Farm

3.5 out of 5
Save 100% on your flight
Price was $705, price is now $441 per person
$441
per person
Jan 23 - Jan 27
found 19 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Price was $914, price is now $686 per person
$686
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Lafayette (LFT) to Albany (ALB)
South Shire

South Shire

4 out of 5
Price was $817, price is now $640 per person
$640
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Lafayette (LFT) to Albany (ALB)
The White House Inn

The White House Inn

3.5 out of 5
Price was $796, price is now $638 per person
$638
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Lafayette (LFT) to Albany (ALB)
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
Price was $759, price is now $638 per person
$638
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Lafayette (LFT) to Albany (ALB)
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
Price was $742, price is now $630 per person
$630
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Lafayette (LFT) to Albany (ALB)
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $912, price is now $816 per person
$816
per person
Jan 15 - Jan 19
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
Price was $1,085, price is now $980 per person
$980
per person
Jan 15 - Jan 19
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
The Four Chimneys Inn

The Four Chimneys Inn

4 out of 5
Price was $787, price is now $762 per person
$762
per person
Jan 15 - Jan 19
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
The Williams Inn

The Williams Inn

4 out of 5
Price was $889, price is now $874 per person
$874
per person
Jan 15 - Jan 19
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)

5-night The Berkshires vacations

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Latham Albany Airport

Baymont by Wyndham Latham Albany Airport

2.5 out of 5
Price was $507, price is now $455 per person
$455
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was $660, price is now $556 per person
$556
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
The Century House, an Ascend Collection Hotel

The Century House, an Ascend Collection Hotel

3 out of 5
Price was $684, price is now $585 per person
$585
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
Price was $648, price is now $561 per person
$561
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
Price was $603, price is now $524 per person
$524
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Tru By Hilton Albany Airport, NY

Tru By Hilton Albany Airport, NY

2.5 out of 5
Price was $667, price is now $583 per person
$583
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Microtel Inn by Wyndham Albany Airport

Microtel Inn by Wyndham Albany Airport

2 out of 5
Price was $565, price is now $498 per person
$498
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Super 8 by Wyndham Latham/Albany Airport

Super 8 by Wyndham Latham/Albany Airport

2 out of 5
Price was $522, price is now $466 per person
$466
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Super 8 by Wyndham Schenectady/Albany Area

Super 8 by Wyndham Schenectady/Albany Area

2 out of 5
Price was $510, price is now $457 per person
$457
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Price was $649, price is now $584 per person
$584
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Hilton Garden Inn Clifton Park

Hilton Garden Inn Clifton Park

3 out of 5
Price was $698, price is now $632 per person
$632
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)
Hilton Garden Inn Albany Medical Center

Hilton Garden Inn Albany Medical Center

3 out of 5
Price was $702, price is now $637 per person
$637
per person
Jan 14 - Jan 19
found 15 hours ago
Roundtrip non-stop flight included
Wilmington (ILM) to Albany (ALB)

6-7 night The Berkshires vacations

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn Albany Airport

Red Roof Inn Albany Airport

2 out of 5
Price was $426, price is now $346 per person
$346
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $672, price is now $508 per person
$508
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Marriott Albany

Marriott Albany

3.5 out of 5
Price was $780, price is now $593 per person
$593
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Price was $798, price is now $634 per person
$634
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $801, price is now $649 per person
$649
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
The Century House, an Ascend Collection Hotel

The Century House, an Ascend Collection Hotel

3 out of 5
Price was $711, price is now $580 per person
$580
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
Price was $680, price is now $555 per person
$555
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was $879, price is now $717 per person
$717
per person
Jan 5 - Jan 12
found 17 hours ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
Homewood Suites by Hilton Albany

Homewood Suites by Hilton Albany

3 out of 5
Price was $803, price is now $657 per person
$657
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Hilton Garden Inn Troy

Hilton Garden Inn Troy

3 out of 5
Price was $773, price is now $633 per person
$633
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Homewood Suites by Hilton Albany Crossgates Mall, NY

Homewood Suites by Hilton Albany Crossgates Mall, NY

3 out of 5
Price was $739, price is now $608 per person
$608
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

3 out of 5
Price was $660, price is now $546 per person
$546
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)

Flight deals to The Berkshires

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Jan 16 - Sun, Jan 18
MCO
Orlando
BDL
Hartford
$69 Roundtrip, found 5 days ago
$69
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Jan 16 from Orlando to Hartford, returning Sun, Jan 18, priced at $69 found 5 days ago
Thu, Feb 26 - Sun, Mar 1
ATL
Atlanta
BDL
Hartford
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Atlanta to Hartford, returning Sun, Mar 1, priced at $118 found 4 days ago
Wed, Jan 21 - Sun, Jan 25
ORD
Chicago
BDL
Hartford
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jan 21 from Chicago to Hartford, returning Sun, Jan 25, priced at $124 found 1 day ago

Top rated hotels for your The Berkshires vacation

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Free Cancellation
Reserve now, pay when you stay
28.42 mi from city center
$101 nightly
The price is $113 total per night
$113 total
Dec 7 - Dec 8
Total with taxes and fees
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.
Pool
Parking included
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
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
Jan 4 - Jan 5, 2026
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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Free Cancellation
Reserve now, pay when you stay
37.59 mi from city center
$197 nightly
The price is $220 total per night
$220 total
Dec 8 - Dec 9
Total with taxes and fees
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
Pet friendly
Parking included
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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.

^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.