Deals on vacations and trips to Sheffield
Save when you book Sheffield package deals
Sheffield flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was $489, price is now $356 per person
$356
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
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.
The Perch Hotel
Save 100% on your flight
Price was $971, price is now $625 per person
$625
per person
Jul 9 - Jul 13
found 9 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
This hotel 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.
Lodges At Cresthaven
Price was $728, price is now $536 per person
$536
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
A restaurant and a 24-hour gym are featured at this lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A business center, a terrace, and a picnic area are also on offer.
The Equinox Golf Resort & Spa
Manchester Village Historic District
Save 100% on your flight
Price was $1,799, price is now $1,334 per person
$1,334
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Hilton Garden Inn Saratoga Springs
Price was $1,217, price is now $923 per person
$923
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Free self parking, a garden, and a lobby fireplace are also offered.
Top Sheffield hotels deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Free Cancellation
Reserve now, pay when you stay
$180 nightly
The price is $201 total per night
$201 total
May 7 - May 8
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.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$113 nightly
The price is $126 total per night
$126 total
May 24 - May 25
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.
Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $103 total per night
$103 total
May 6 - May 7
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.
The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $208 total per night
$208 total
May 17 - May 18
Total with taxes and fees
This historic hotel includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street South Lee MA
Free Cancellation
$145 nightly
The price is $162 total per night
$162 total
May 10 - May 11
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.
The Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Free Cancellation
$114 nightly
The price is $128 total per night
$128 total
May 11 - May 12
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.
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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