Sheffield Vacations

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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 ...
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 business center. Our guests praise the helpful staff and the clean rooms in ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
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 ...
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 ...
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
10.88 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 ...
Prospect Berkshires

Prospect Berkshires

2 out of 5
50 Prospect Lake Rd, Egremont, MA
12.1 km from city center
Stay at this hotel in Great Barrington. Enjoy free WiFi, free parking, and a sauna. Popular attractions Catamount Aerial Adventure Park and Catamount Ski Area ...
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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.

Delta
Tue, Nov 18 - Thu, Dec 4
SFO
San Francisco Intl.
ALB
Albany Intl.
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 18 from San Francisco Intl. to Albany Intl., returning Thu, Dec 4, priced at $277 found 1 day ago
American Airlines
Sun, Nov 23 - Wed, Dec 3
SFO
San Francisco Intl.
ALB
Albany Intl.
$325 Roundtrip, found 1 day ago
$325
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Nov 23 from San Francisco Intl. to Albany Intl., returning Wed, Dec 3, priced at $325 found 1 day ago
United
Sun, Nov 23 - Wed, Dec 3
SFO
San Francisco Intl.
ALB
Albany Intl.
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select United flight, departing Sun, Nov 23 from San Francisco Intl. to Albany Intl., returning Wed, Dec 3, priced at $364 found 1 day ago
JetBlue Airways
Tue, Aug 26 - Tue, Sep 9
LAX
Los Angeles Intl.
ALB
Albany Intl.
$478 Roundtrip, found 5 days ago
$478
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Aug 26 from Los Angeles Intl. to Albany Intl., returning Tue, Sep 9, priced at $478 found 5 days ago