Cheap Vacations in Berkshire County

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Berkshire County vacations

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $595, price is now $478 per person
$478
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $1,215, price is now $891 per person
$891
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $762, price is now $614 per person
$614
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Stockade District
Price was $687, price is now $570 per person
$570
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
Price was $891, price is now $782 per person
$782
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $603, price is now $532 per person
$532
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $701, price is now $621 per person
$621
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
Price was $808, price is now $723 per person
$723
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)
Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $956, price is now $872 per person
$872
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Kingston Carriage House

Kingston Carriage House

4 out of 5
Rondout
Price was $827, price is now $759 per person
$759
per person
Aug 21 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

3-night Berkshire County vacations

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

3 out of 5
Price was $447, price is now $398 per person
$398
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Hudson (HCC)
The Perch Hotel

The Perch Hotel

2 out of 5
Price was $636, price is now $458 per person
$458
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $1,215, price is now $891 per person
$891
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $639, price is now $511 per person
$511
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $770, price is now $621 per person
$621
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)
Hotel Kinsley

Hotel Kinsley

3.5 out of 5
Price was $687, price is now $570 per person
$570
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
The Haüs Windham

The Haüs Windham

2 out of 5
Price was $584, price is now $492 per person
$492
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Hudson (HCC)
Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

3.5 out of 5
Price was $724, price is now $620 per person
$620
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
The Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $524, price is now $454 per person
$454
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Albany (ALB)
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
Price was $891, price is now $782 per person
$782
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)
Eastwind Windham

Eastwind Windham

3.5 out of 5
Price was $605, price is now $535 per person
$535
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Washington (WAS) to Hudson (HCC)
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
Price was $808, price is now $723 per person
$723
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Orange County (SNA) to Albany (ALB)

4-night Berkshire County vacations

Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $595, price is now $478 per person
$478
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $762, price is now $614 per person
$614
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Yankee Inn

The Yankee Inn

2.5 out of 5
Price was $701, price is now $621 per person
$621
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
Price was $601, price is now $559 per person
$559
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
Price was $760, price is now $726 per person
$726
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)

5-night Berkshire County vacations

Price found within the past 48 hours. Click for updated prices.
Albany Plaza Hotel

Albany Plaza Hotel

2 out of 5
Price was $408, price is now $368 per person
$368
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) 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 $681, price is now $572 per person
$572
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Albany Airport Inn

Albany Airport Inn

2.5 out of 5
Price was $550, price is now $467 per person
$467
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Super 8 by Wyndham Latham/Albany Airport

Super 8 by Wyndham Latham/Albany Airport

2 out of 5
Price was $477, price is now $413 per person
$413
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Price was $818, price is now $710 per person
$710
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Hilton Albany

Hilton Albany

3.5 out of 5
Price was $632, price is now $550 per person
$550
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Travelodge Inn & Suites by Wyndham Albany

Travelodge Inn & Suites by Wyndham Albany

2.5 out of 5
Price was $453, price is now $395 per person
$395
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Howard Johnson by Wyndham Albany

Howard Johnson by Wyndham Albany

2 out of 5
Price was $442, price is now $386 per person
$386
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Baymont by Wyndham Latham Albany Airport

Baymont by Wyndham Latham Albany Airport

2.5 out of 5
Price was $429, price is now $376 per person
$376
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

2.5 out of 5
Price was $574, price is now $505 per person
$505
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Fairfield Inn & Suites by Marriott Albany Downtown

Fairfield Inn & Suites by Marriott Albany Downtown

3 out of 5
Price was $840, price is now $740 per person
$740
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)
Tru By Hilton Albany Airport, NY

Tru By Hilton Albany Airport, NY

2.5 out of 5
Price was $572, price is now $515 per person
$515
per person
Sep 3 - Sep 8
found 17 hours ago
Roundtrip non-stop flight included
Orlando (ORL) to Albany (ALB)

Top places to visit in Berkshire County

A town hall with a central dome and columns, surrounded by trees and people.
FlightsFlightsHotelsHotels

Lenox

Lenox

Flight deals to Berkshire County

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

Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale
ALB
Albany
$98 Roundtrip, found 3 days ago
$98
Roundtrip
found 3 days ago
Select Allegiant Air flight, departing Thu, Sep 3 from Fort Lauderdale to Albany, returning Sun, Sep 6, priced at $98 found 3 days ago
Sat, Aug 29 - Mon, Aug 31
MCO
Orlando
BDL
Hartford
$140 Roundtrip, found 4 days ago
$140
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando to Hartford, returning Mon, Aug 31, priced at $140 found 4 days ago
Fri, Aug 28 - Tue, Sep 1
SJU
San Juan
BDL
Hartford
$156 Roundtrip, found 1 day ago
$156
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 28 from San Juan to Hartford, returning Tue, Sep 1, priced at $156 found 1 day ago

Top rated hotels for your Berkshire County 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
8 mi from city center
$151 nightly
The price is $169 total per night
$169 total
Jul 21 - Jul 22
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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Free Cancellation
18.65 mi from city center
$161 nightly
The price is $179 total per night
$179 total
Aug 16 - Aug 17
Total with taxes and fees
With a stay at Hotel Downstreet, an Ascend Collection Hotel, you'll be centrally located in North Adams, a 1-minute drive from Massachusetts Museum of Contemporary Art and 10 minutes from Williams College.
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free Cancellation
18.67 mi from city center
$118 nightly
The price is $132 total per night
$132 total
Aug 9 - Aug 10
Total with taxes and fees
With a stay at Quality Inn Great Barrington in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 8 minutes by foot from Housatonic River.
Breakfast included
Parking included
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See all available properties in Berkshire County
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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.

Top Picks

^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.