Southfield 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

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
19.46 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 Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
21.13 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 by the Lenox Collection

The Constance by the Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
28.64 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. ...
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
14.84 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 ...
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd, Lenox, MA
30.96 km from city center
Stay at this 3-star business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
24.58 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

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
22.13 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 ...
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
15.5 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 ...
The Whitlock

The Whitlock

2 out of 5
16 Church St, Lenox, MA
28.68 km from city center
Stay at this hotel in Lenox. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood ...
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2 out of 5
492 East Main St, Torrington, CT
34.23 km from city center
Book a stay at this business-friendly motel in Torrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road, Great Barrington, MA
17.57 km from city center
Stay at this 3-star motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff in our reviews. Popular ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
15.06 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 ...
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
400 Stockbridge Rd, Great Barrington, MA
16.81 km from city center
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

2.5 out of 5
395 Winsted Rd, Torrington, CT
32.25 km from city center
Book a stay at this business-friendly hotel in Torrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
15.04 km from city center
Stay at this motel in Great Barrington. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Don't see what you're looking for?
See all available properties in Southfield
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.

Spirit Airlines
Sat, Aug 16 - Fri, Aug 22
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Aug 22, priced at $98 found 1 day ago
Frontier Airlines
Mon, Aug 25 - Mon, Sep 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$119 Roundtrip, found 6 hours ago
$119
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Mon, Aug 25 from Orlando Intl. to Bradley Intl., returning Mon, Sep 8, priced at $119 found 6 hours ago
JetBlue Airways
Wed, Aug 20 - Sat, Aug 30
MCO
Orlando Intl.
ALB
Albany Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Aug 20 from Orlando Intl. to Albany Intl., returning Sat, Aug 30, priced at $137 found 5 days ago
United
Thu, Oct 16 - Tue, Oct 21
ORD
O'Hare Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 16 from O'Hare Intl. to Bradley Intl., returning Tue, Oct 21, priced at $137 found 3 days ago
American Airlines
Sat, Aug 16 - Wed, Aug 20
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$168 Roundtrip, found 10 hours ago
$168
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Aug 16 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Wed, Aug 20, priced at $168 found 10 hours ago