Middlefield Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Elizabeth Massa Peroulakis
Top Hotel Deals
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 a 24-hour front desk. Our guests praise the helpful staff ...
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
21.61 km from city center
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
20.43 km from city center
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
Hotel Northampton
36 King Street, Northampton, MA
31.76 km from city center
Stay at this 3.5-star historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
Berkshires Untold
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 ...
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 ...
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 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. ...
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 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 ...
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 ...
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
33.6 km from city center
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
26.16 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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, Aug 21 - Mon, Aug 25
MCO
Orlando Intl.
BDL
Bradley Intl.
$104 Roundtrip, found 6 days ago
$104
Roundtrip
found 6 days ago
Thu, Aug 21 - Mon, Aug 25
MCO
Orlando Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Sat, Oct 4 - Tue, Oct 7
TPA
Tampa Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Fri, Oct 10 - Sun, Oct 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
Tue, Oct 7 - Wed, Oct 15
ORD
O'Hare Intl.
BDL
Bradley Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Best points of interest in Middlefield
- Skyline Trail Vacations
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- Smith College Vacations
- National Shrine of the Divine Mercy Vacations
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- Berkshire East Ski Resort Vacations
- Norman Rockwell Museum Vacations
- Ski Butternut Vacations
- Connecticut River Vacations
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