Sheffield 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

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
0.5 km from city center
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
9.19 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 ...
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
33.36 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. ...
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
19.43 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 ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
31.44 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 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
27.95 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. ...
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
33.41 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 ...
Prospect Berkshires

Prospect Berkshires

2 out of 5
50 Prospect Lake Rd, Egremont, MA
12.07 km from city center
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Catamount Aerial Adventure Park and Catamount ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
19.48 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 ...
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 out of 5
445 Pittsfield Rd, Lenox, MA
33.16 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 helpful staff ...
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
24.8 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
23.11 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 ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
34.46 km from city center
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
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
11.5 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 ...
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3 out of 5
70 Pittsfield Rd, Lenox, MA
30.52 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. ...
Don't see what you're looking for?
See all available properties in Sheffield
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.

JetBlue Airways
Tue, Aug 12 - Tue, Aug 19
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$177 Roundtrip, found 2 days ago
$177
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Aug 12 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Aug 19, priced at $177 found 2 days ago
Delta
Sat, Aug 16 - Wed, Aug 20
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$217 Roundtrip, found 2 days ago
$217
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 16 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Wed, Aug 20, priced at $217 found 2 days ago
United
Thu, Aug 14 - Mon, Aug 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$237 Roundtrip, found 2 days ago
$237
Roundtrip
found 2 days ago
Select United flight, departing Thu, Aug 14 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Aug 18, priced at $237 found 2 days ago
American Airlines
Thu, Aug 14 - Mon, Aug 18
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Aug 14 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Mon, Aug 18, priced at $242 found 2 days ago
Alaska Airlines
Thu, Jul 31 - Sun, Aug 3
LAX
Los Angeles Intl.
ALB
Albany Intl.
$742 Roundtrip, found 4 days ago
$742
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Thu, Jul 31 from Los Angeles Intl. to Albany Intl., returning Sun, Aug 3, priced at $742 found 4 days ago