
Middlefield Vacations
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Photo by Elizabeth Massa Peroulakis
Top Hotel Deals

Life House Berkshires
194 Pittsfield Rd, Lenox, MA
21.63 km from city center
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...

The Ellery
259 Elm Street, Northampton, MA
30.48 km from city center
Stay at this 3.5-star B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
22.79 km from city center
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
21.61 km from city center
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...

The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
20.35 km from city center
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...

Quality Inn & Suites Northampton - Amherst
117 Conz St, Northampton, MA
32.32 km from city center
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...

Fairfield Inn & Suites Springfield Northampton/Amherst
115A Conz Street, Northampton, MA
32.24 km from city center
Stay at this 3-star business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...

The Red Lion Inn
30 Main Street, Stockbridge, MA
25.48 km from city center
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...

The Constance, The Whitlock, & The Dewey By The Lenox Collection
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
22.24 km from city center
Stay at this 3.5-star hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
33.02 km from city center
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in ...

Hotel On North
297 North Street, Pittsfield, MA
22.7 km from city center
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
22.62 km from city center
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...

Howard Johnson by Wyndham Lenox
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
21.48 km from city center
Stay at this motel in Lenox. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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 Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Jun 12 - Sat, Jun 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$107 Roundtrip, found 6 days ago
$107
Roundtrip
found 6 days ago

Thu, May 29 - Sun, Jun 1
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago

Sat, Jul 12 - Thu, Jul 17
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$162 Roundtrip, found 2 days ago
$162
Roundtrip
found 2 days ago

Thu, Jun 12 - Tue, Jun 17
LAX
Los Angeles Intl.
BDL
Bradley Intl.
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
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