Vacations in The Berkshires

Vacations in The Berkshires

2 travelers

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$434 - $658$658 - $883$883 - $1,107$1,107 - $1,332$1,332+ per night

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Most popular The Berkshires flight and hotel deals

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Hotel on North - Pittsfield
Hotel on North - Pittsfield
Hotel on North
9.2 Wonderful
Parking
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$613
9 Academy - Salisbury - Living room
9 Academy - Salisbury - Living room
9 Academy
9.8 Wonderful
Parking
Free Wi-Fi
New York LaGuardia
Meals not included
3 nights + flight
$1,332
Hampton Inn & Suites Berkshires-Lenox - Lenox - Building
Hampton Inn & Suites Berkshires-Lenox - Lenox - Building
Hampton Inn & Suites Berkshires-Lenox
8.3 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$498
Best Western Plus Berkshire Hills Inn & Suites - Pittsfield - Bedroom
Best Western Plus Berkshire Hills Inn & Suites - Pittsfield - Bedroom
Best Western Plus Berkshire Hills Inn & Suites
7.5 Good
Parking
Free Wi-Fi
Pet friendly
New York LaGuardia
Breakfast
3 nights + flight
$465
Berkshires Untold - Lenox - Building
Berkshires Untold - Lenox - Building
Berkshires Untold
8.3 Very good
Parking
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$647
The Cornell Inn, Lenox & The Berkshires - Lenox - Bedroom
The Cornell Inn, Lenox & The Berkshires - Lenox - Bedroom
The Cornell Inn, Lenox & The Berkshires
8.6 Very good
Parking
Free Wi-Fi
New York LaGuardia
Breakfast
3 nights + flight
$701
Fairbridge Inn Express Pittsfield - Pittsfield - Bedroom
Fairbridge Inn Express Pittsfield - Pittsfield - Bedroom
Fairbridge Inn Express Pittsfield
4.3 Mediocre
Parking
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$433
The Yankee Inn - Lenox - Outdoors view
The Yankee Inn - Lenox - Outdoors view
The Yankee Inn
8.4 Very good
Parking
Free Wi-Fi
Pool
New York LaGuardia
Breakfast
3 nights + flight
$480
Howard Johnson by Wyndham Lenox - Lenox - Bedroom
Howard Johnson by Wyndham Lenox - Lenox - Bedroom
Howard Johnson by Wyndham Lenox
6.5 Okay
Parking
Pool
New York LaGuardia
Meals not included
3 nights + flight
$481
Hilton Garden Inn Lenox Pittsfield - Pittsfield - Patio
Hilton Garden Inn Lenox Pittsfield - Pittsfield - Patio
Hilton Garden Inn Lenox Pittsfield
8.5 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$596
Berkshire Mountain Lodge - Pittsfield - Building
Berkshire Mountain Lodge - Pittsfield - Building
Berkshire Mountain Lodge
8.7 Very good
Parking
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
$482
Prospect Berkshires - Great Barrington - Bedroom
Prospect Berkshires - Great Barrington - Bedroom
Prospect Berkshires
9.6 Wonderful
Parking
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
$1,033
The Red Lion Inn - Stockbridge - Lounge
The Red Lion Inn - Stockbridge - Lounge
The Red Lion Inn
8.1 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$785
Berkshire Inn - Pittsfield - Bedroom
Berkshire Inn - Pittsfield - Bedroom
Berkshire Inn
7.2 Good
Parking
Free Wi-Fi
Pool
New York LaGuardia
Meals not included
3 nights + flight
$451
Holiday Inn & Suites Pittsfield-Berkshires By IHG - Pittsfield - Pool
Holiday Inn & Suites Pittsfield-Berkshires By IHG - Pittsfield - Pool
Holiday Inn & Suites Pittsfield-Berkshires By IHG
7.3 Good
Free Wi-Fi
Pool
Spa
New York LaGuardia
Meals not included
3 nights + flight
$482
The Little Lion - Great Barrington - Outdoors view
The Little Lion - Great Barrington - Outdoors view
The Little Lion
7.6 Good
Parking
Free Wi-Fi
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
$501

When to book a vacation in The Berkshires

Price includes flights and 3 nights accommodation for 2 travelers. Prices are not fixed and may vary with time.

Where to stay in The Berkshires

Our map will help you find the perfect place to stay for your vacation in The Berkshires by showing you the exact location of each hotel.

Everything you need to know for your vacation in The Berkshires