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.
Lakefront Terrace Resort
Price was $1,337, price is now $1,053 per person
$1,053
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Albany (ALB)
This hotel features a private beach, a marina, and a restaurant. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Hotel Brookmere & Arbor Spa
Price was $1,621, price is now $1,288 per person
$1,288
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Albany (ALB)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 4 conference rooms, along with free WiFi in public areas. Enjoy the seasonal outdoor pool and perks like free self parking.
Lodges At Cresthaven
Save 100% on your flight
Price was $6,054, price is now $4,885 per person
$4,885
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip flight included
Detroit (DTT) 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 Landing Hotel at Rivers Casino & Resort
Nothside
Price was $1,354, price is now $1,122 per person
$1,122
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Detroit (DTT) 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.
Wilburton Inn
Save 100% on your flight
Price was $2,062, price is now $1,720 per person
$1,720
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip flight included
Detroit (DTT) to Albany (ALB)
This hotel features an outdoor tennis court and a seasonal outdoor pool. Families will appreciate the picnic area and in-room childcare. Guests will appreciate free perks like free self parking and WiFi in public areas.
Top Sheffield hotels deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $168 total per night
$168 total
Apr 30 - May 1
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
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Sheffield MA
This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $97 total per night
$97 total
Apr 21 - Apr 22
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
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
May 19 - May 20
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 Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$172 nightly
The price is $192 total per night
$192 total
Apr 30 - May 1
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.
Pool
Spa
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Free Cancellation
Reserve now, pay when you stay
$75 nightly
The price is $84 total per night
$84 total
Apr 26 - Apr 27
Total with taxes and fees
A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.
Breakfast included
Parking included
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.
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.
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.
Frequently asked questions
Photos of local treasures
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