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 ...
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 ...
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

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 ...
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. ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
22.62 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Quality Inn

Quality Inn

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 ...
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 ...
Fairfield Inn & Suites Springfield Northampton/Amherst

Fairfield Inn & Suites Springfield Northampton/Amherst

3 out of 5
115A Conz Street Northampton MA
32.24 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 in our reviews. ...
The Ellery

The Ellery

3.5 out of 5
259 Elm Street Northampton MA
30.49 km from city center
Stay at this hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
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, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff 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 ...
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
22.7 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
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 ...
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
35.71 km from city center
Stay at this campground in Williamstown. Enjoy free parking, breakfast (surcharge), and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd Great Barrington MA
31.05 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 helpful staff and the ...
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.

Frontier Airlines
Thu, Feb 26 - Sun, Mar 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$66 Roundtrip, found 5 days ago
$66
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Orlando Intl. to Bradley Intl., returning Sun, Mar 1, priced at $66 found 5 days ago
Breeze Airways
Tue, Apr 7 - Wed, Apr 22
MCO
Orlando Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 6 days ago
$132
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Tue, Apr 7 from Orlando Intl. to Bradley Intl., returning Wed, Apr 22, priced at $132 found 6 days ago
Delta
Tue, Apr 21 - Thu, May 7
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$139 Roundtrip, found 10 hours ago
$139
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Apr 21 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Thu, May 7, priced at $139 found 10 hours ago
JetBlue Airways
Tue, May 19 - Tue, May 26
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$147 Roundtrip, found 3 days ago
$147
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, May 19 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, May 26, priced at $147 found 3 days ago
Southwest Airlines
Tue, Apr 7 - Wed, Apr 22
MCO
Orlando Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Apr 7 from Orlando Intl. to Bradley Intl., returning Wed, Apr 22, priced at $167 found 6 days ago