Deals on vacations and trips to Sheffield
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Sheffield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Kingston Carriage House
Roundout
Price was $922, price is now $752 per person
$752
per person
Dec 18 - Dec 21
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
This bed & breakfast features free WiFi in public areas, a communal living room, and concierge services. Enjoy the free continental breakfast each morning. A virtual front desk are provided for your convenience.
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views
Price was $1,142, price is now $949 per person
$949
per person
Dec 18 - Dec 21
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Hutton Brickyards Riverfront Hotel + Venue
Price was $865, price is now $729 per person
$729
per person
Dec 18 - Dec 21
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A garden, a picnic area, and luggage storage are also on offer.
Hasbrouck House
Price was $1,183, price is now $1,016 per person
$1,016
per person
Dec 18 - Dec 21
found 3 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free valet parking. Enjoy the sauna and perks like free self parking.
Top Sheffield hotels deals
Wilder House Berkshires
48 S Main Street, Sheffield, MA
Free Cancellation
Reserve now, pay when you stay
$155 nightly
The price is $174 total per night
$174 total
Oct 27 - Oct 28
Total with taxes and fees
This bed & breakfast features free self parking and a garden. Free cooked-to-order breakfast is served. A lobby fireplace, a communal living room, and a picnic area are also on offer.
Breakfast included
Parking included
Guesthouse Cabin vacation rentals in Berkshire County
$640 nightly
The price is $715 total per night
$715 total
Oct 26 - Oct 27
Total with taxes and fees
This cabin includes a garden and barbecue grills.
Kitchen
Pet friendly
Antique Farmhouse Totally Restored
A water park and a hot tub are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and childcare is an added bonus. There's a gym on site, and laundry facilities and barbecue grills are also offered.
Hot Tub
Kitchen
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
$113 nightly
The price is $126 total per night
$126 total
Nov 2 - Nov 3
Total with taxes and fees
This lodge features an indoor pool and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $98 total per night
$98 total
Nov 2 - Nov 3
Total with taxes and fees
A restaurant and a bar/lounge are featured at this lodge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a lobby fireplace, and express check-in are also on offer.
Pet friendly
Parking included
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St, Lee, MA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $119 total per night
$119 total
Nov 2 - Nov 3
Total with taxes and fees
A restaurant and a 24-hour gym are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A 24-hour business center, a picnic area, and laundry facilities are also on offer.
Breakfast included
Pet friendly
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.
Popular places to visit
Magnolia Bluffs Casino
Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails.
Ashley House
You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.
Bartholomew's Cobble
You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
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