Middlefield Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
33.02 km from city center
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
33.61 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 ...
The Yankee Inn

The Yankee Inn

2.5 out of 5
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 ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
21.61 km from city center
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
Hotel Northampton

Hotel Northampton

3.5 out of 5
36 King Street Northampton MA
31.76 km from city center
Book a stay at this historic hotel in Northampton. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
25.48 km from city center
Book a stay at this historic hotel in Stockbridge. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
21.63 km from city center
Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Quality Inn & Suites Northampton - Amherst

Quality Inn & Suites Northampton - Amherst

2.5 out of 5
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 ...
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
30.49 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 breakfast and the helpful ...
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
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 ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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

2.5 out of 5
1055 South Street Pittsfield MA
21.4 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

2.5 out of 5
170 Housatonic Street Lee MA
19.47 km from city center
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
20.35 km from city center
Stay at this hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions ...
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
190 Meadow Street South Lee MA
22.79 km from city center
Book a stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in ...
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
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 ...
Don't see what you're looking for?
See all available properties in Middlefield
View all properties
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.

Breeze Airways
Wed, Aug 12 - Mon, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$130 Roundtrip, found 6 days ago
$130
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Mon, Aug 31, priced at $130 found 6 days ago
Frontier Airlines
Wed, Aug 12 - Mon, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$133 Roundtrip, found 6 days ago
$133
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Mon, Aug 31, priced at $133 found 6 days ago
Delta
Sat, Oct 17 - Tue, Oct 20
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Oct 17 from Ronald Reagan Washington National to Bradley Intl., returning Tue, Oct 20, priced at $197 found 3 days ago
American Airlines
Thu, Aug 6 - Tue, Aug 11
TPA
Tampa Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 23 hours ago
$217
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Thu, Aug 6 from Tampa Intl. to Bradley Intl., returning Tue, Aug 11, priced at $217 found 23 hours ago
United
Thu, Aug 6 - Tue, Aug 11
TPA
Tampa Intl.
BDL
Bradley Intl.
$227 Roundtrip, found 23 hours ago
$227
Roundtrip
found 23 hours ago
Select United flight, departing Thu, Aug 6 from Tampa Intl. to Bradley Intl., returning Tue, Aug 11, priced at $227 found 23 hours ago