Vacations in The Berkshires

Vacations in The Berkshires

2 travellers

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C$ 611 - C$ 837C$ 837 - C$ 1,061C$ 1,061 - C$ 1,286C$ 1,286 - C$ 1,512C$ 1,512+ 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
C$ 864
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
C$ 701
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
C$ 656
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
C$ 911
The Cornell Inn, Lenox & The Berkshires - Lenox - Bedroom
The Cornell Inn, Lenox & The Berkshires - Lenox - Bedroom
The Cornell Inn, Lenox & The Berkshires
8.7 Very good
Parking
Free Wi-Fi
New York LaGuardia
Breakfast
3 nights + flight
C$ 988
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
C$ 610
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
C$ 676
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
C$ 677
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
C$ 840
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
C$ 679
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
C$ 1,455
The Red Lion Inn - Stockbridge - Lounge
The Red Lion Inn - Stockbridge - Lounge
The Red Lion Inn
8.2 Very good
Parking
Free Wi-Fi
Pool
Pet friendly
New York LaGuardia
Meals not included
3 nights + flight
C$ 1,106
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
C$ 636
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
C$ 679
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires - Great Barrington - Building
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires - Great Barrington - Building
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
8.8 Very good
Parking
Free Wi-Fi
Pool
New York LaGuardia
Breakfast
3 nights + flight
C$ 888
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
C$ 706

When to book a vacation in The Berkshires

Price includes flights and 3 nights accommodation for 2 travellers. 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