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 ...
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 ...
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
34.46 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 ...
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
31.44 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 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
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 ...
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
19.48 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. ...
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
24.8 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 ...
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
Book a stay at this business-friendly hotel in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise 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 ...
Prospect Berkshires

Prospect Berkshires

3 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 ...
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
33.93 km from city center
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Guido's Marketplace and Herman Melville's Arrowhead ...
The Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road Great Barrington MA
14.58 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 in our reviews. Popular attractions ...
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 ...
Element Lenox Berkshires

Element Lenox Berkshires

3 out of 5
130 PITTSFIELD ROAD Lenox MA
30.93 km from city center
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Kennedy Park and Pleasant Valley ...
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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.

JetBlue Airways
Thu, Feb 26 - Tue, Mar 10
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$324 Roundtrip, found 4 days ago
$324
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, Feb 26 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Tue, Mar 10, priced at $324 found 4 days ago
Delta
Mon, Mar 2 - Tue, Mar 10
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Mar 2 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Tue, Mar 10, priced at $339 found 4 days ago
Southwest Airlines
Wed, Feb 18 - Tue, Feb 24
LAX
Los Angeles Intl.
ALB
Albany Intl.
$367 Roundtrip, found 2 hours ago
$367
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Wed, Feb 18 from Los Angeles Intl. to Albany Intl., returning Tue, Feb 24, priced at $367 found 2 hours ago
American Airlines
Wed, Feb 18 - Tue, Feb 24
LAX
Los Angeles Intl.
ALB
Albany Intl.
$375 Roundtrip, found 2 hours ago
$375
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Feb 18 from Los Angeles Intl. to Albany Intl., returning Tue, Feb 24, priced at $375 found 2 hours ago
United
Sun, Mar 1 - Sun, Mar 8
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$456 Roundtrip, found 4 days ago
$456
Roundtrip
found 4 days ago
Select United flight, departing Sun, Mar 1 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Sun, Mar 8, priced at $456 found 4 days ago