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

Wilder House Berkshires
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 ...

Life House Berkshires
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 ...

Quality Inn
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 ...

The Yankee, Trademark Collection by Wyndham
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 ...

The Black Swan Lee - Lenox, Ascend Hotel Collection
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 ...

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 ...

The Red Lion Inn
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 ...

Berkshire Mountain Lodge
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 ...

Howard Johnson by Wyndham Lenox
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. ...

The Constance, The Whitlock, & The Dewey By The Lenox Collection
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. ...

Quality Inn
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 ...

Holiday Inn Express Hotel & Suites Great Barrington by IHG
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
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. ...
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.

Sun, Aug 31 - Wed, Sep 10
PHX
Sky Harbor Intl.
ALB
Albany Intl.
$307 Roundtrip, found 4 days ago
$307
Roundtrip
found 4 days ago

Tue, Jun 3 - Tue, Jun 3
LAX
Los Angeles Intl.
ALB
Albany Intl.
$307 Roundtrip, found 3 days ago
$307
Roundtrip
found 3 days ago

Sat, Dec 20 - Sat, Jan 3
DFW
Dallas-Fort Worth Intl.
ALB
Albany Intl.
$396 Roundtrip, found 3 days ago
$396
Roundtrip
found 3 days ago

Wed, May 7 - Sun, May 25
TPA
Tampa Intl.
ALB
Albany Intl.
$413 Roundtrip, found 6 days ago
$413
Roundtrip
found 6 days ago
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations