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.
The Dewey
Price was $550, price is now $442 per person
$442
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This guesthouse doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Prospect Berkshires
Price was $730, price is now $523 per person
$523
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the sauna and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a picnic area are also on offer.
The Landing Hotel at Rivers Casino & Resort
Nothside
Price was $809, price is now $617 per person
$617
per person
Mar 6 - Mar 10
found 3 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Albany (ALB)
A casino, 5 restaurants, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Free self parking is free for guests, and you can enjoy a meal in one of the 2 coffee shops/cafes.
Gedney Farm
Price was $606, price is now $466 per person
$466
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A terrace, a garden, and a communal living room are also on offer.
The Cornell Inn, Lenox & The Berkshires
Price was $647, price is now $503 per person
$503
per person
Mar 16 - Mar 19
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.
Top Sheffield hotels deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Free Cancellation
Reserve now, pay when you stay
$179 nightly
The price is $200 total per night
$200 total
Jan 19 - Jan 20
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
Sheffield MA
$621 nightly
The price is $694 total per night
$694 total
Jan 13 - Jan 14
Total with taxes and fees
This cabin includes a garden and barbecue grills.
Kitchen
Pet friendly
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $120 total per night
$120 total
Feb 9 - Feb 10
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
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $113 total per night
$113 total
Jan 19 - Jan 20
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$122 nightly
The price is $136 total per night
$136 total
Jan 13 - Jan 14
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
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Free Cancellation
$130 nightly
The price is $145 total per night
$145 total
Jan 14 - Jan 15
Total with taxes and fees
This hotel features 2 outdoor pools, 2 indoor pools, and a poolside bar. There's fun for all ages with mini golf and a playground, and families will appreciate the picnic area. Enjoy the seasonal outdoor pool and conveniences like a coffee shop and barbecue grills.
Pool
Air conditioning
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.
Drury Preserve
You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Frequently asked questions
Photos of local treasures
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