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.
Vacation Village in the Berkshires
Price was $673, price is now $494 per person
$494
per person
Feb 14 - Feb 17
found 20 hours ago
Roundtrip non-stop flight included
San Jose (SJC) to Albany (ALB)
This condo features an outdoor pool and an indoor pool. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
Hotel Brookmere & Arbor Spa
Price was $679, price is now $499 per person
$499
per person
Feb 14 - Feb 17
found 20 hours ago
Roundtrip non-stop flight included
San Jose (SJC) 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.
South Shire
Price was $729, price is now $566 per person
$566
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, luggage storage, and concierge services are also on offer.
Aspen At Manchester
Price was $960, price is now $761 per person
$761
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A terrace, a garden, and a lobby fireplace are also on offer.
The Manchester View
Price was $742, price is now $610 per person
$610
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Albany (ALB)
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage 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
$155 nightly
The price is $174 total per night
$174 total
Dec 9 - Dec 10
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
Antique Farmhouse Totally Restored
Sheffield MA
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.
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $135 total per night
$135 total
Dec 7 - Dec 8
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.
The Red Lion Inn
30 Main Street Stockbridge MA
Free Cancellation
Reserve now, pay when you stay
$184 nightly
The price is $206 total per night
$206 total
Dec 21 - Dec 22
Total with taxes and fees
This smoke-free 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. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Pool
Spa
Berkshires Untold
194 Pittsfield Rd Lenox MA
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $115 total per night
$115 total
Nov 30 - Dec 1
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 Black Swan Lee - Lenox, an Ascend Collection Hotel
435 Laurel St Lee MA
Free Cancellation
$106 nightly
The price is $119 total per night
$119 total
Dec 19 - Dec 20
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
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.
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.
Bartholomews Cobble
Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.
Frequently asked questions
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