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.
Brook Bound Inn
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
A seasonal outdoor pool, free self parking, and barbecue grills are featured at this hotel. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
The Governor's Rock Motel DF ROCKLLC
per person
Oct 3 - Oct 5
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls and an off-leash area. A terrace, a garden, and a picnic area 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
$225 nightly
The price is $251 total per night
$251 total
Jul 27 - Jul 28
Total includes 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
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.
Hot Tub
Kitchen
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free Cancellation
$172 nightly
The price is $192 total per night
$192 total
Jul 30 - Jul 31
Total includes 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
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$199 nightly
The price is $222 total per night
$222 total
Jul 27 - Jul 28
Total includes 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
$104 nightly
The price is $116 total per night
$116 total
Aug 17 - Aug 18
Total includes 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
$221 nightly
The price is $247 total per night
$247 total
Aug 25 - Aug 26
Total includes 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
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.
Bartholomew's Cobble
You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
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