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 $977, price is now $742 per person
$742
per person
Jun 4 - Jun 10
found 3 hours ago
Roundtrip flight included
San Francisco (SFO) 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.
Vacation Village in the Berkshires
Price was $1,002, price is now $788 per person
$788
per person
Jun 4 - Jun 10
found 3 hours ago
Roundtrip flight included
San Francisco (SFO) 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.
Prospect Berkshires
Price was $1,107, price is now $898 per person
$898
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Forget-me-not by Avantstay Bold Lakefront Escape
Save 100% on your flight
Price was $4,625, price is now $3,751 per person
$3,751
per person
Jun 22 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
A sauna is featured at this cottage, along with free WiFi in public areas and barbecue grills.
Sleeps 40 Heated Pool Hot Tub Fire Pit Game Room Brookside Mountain Retreat by Avantstay
Save 100% on your flight
Price was $4,773, price is now $3,876 per person
$3,876
per person
Jun 21 - Jun 24
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.
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 4 - May 5
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
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 31 - Jun 1
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
$92 nightly
The price is $103 total per night
$103 total
May 4 - May 5
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 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 4 - May 5
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
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 4 - May 5
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
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.
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.
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.
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Photos of local treasures
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