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 Inn

The Yankee Inn

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 ...
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 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 ...
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. ...
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, free parking, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
33.93 km from city center
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and ...
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 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 ...
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

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 ...
The Whitlock

The Whitlock

2 out of 5
16 Church St Lenox MA
28.07 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 ...
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 Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
203 Main St Lenox MA
29.11 km from city center
Stay at this B&B in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular ...
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 a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
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 ...
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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
Mon, Aug 31 - Sun, Sep 13
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Aug 31 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Sun, Sep 13, priced at $232 found 2 days ago
Delta
Sun, Aug 30 - Tue, Sep 15
FLL
Fort Lauderdale - Hollywood Intl.
ALB
Albany Intl.
$242 Roundtrip, found 2 days ago
$242
Roundtrip
found 2 days ago
Select Delta flight, departing Sun, Aug 30 from Fort Lauderdale - Hollywood Intl. to Albany Intl., returning Tue, Sep 15, priced at $242 found 2 days ago
American Airlines
Thu, Oct 15 - Mon, Oct 19
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Oct 15 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Mon, Oct 19, priced at $319 found 4 days ago
United
Tue, Aug 18 - Wed, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$319 Roundtrip, found 5 days ago
$319
Roundtrip
found 5 days ago
Select United flight, departing Tue, Aug 18 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Wed, Aug 26, priced at $319 found 5 days ago
Southwest Airlines
Thu, Oct 15 - Mon, Oct 19
ATL
Hartsfield-Jackson Atlanta Intl.
ALB
Albany Intl.
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Oct 15 from Hartsfield-Jackson Atlanta Intl. to Albany Intl., returning Mon, Oct 19, priced at $319 found 4 days ago