Sheffield Vacations from $492
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Your Sheffield Vacation
The stress-free way to experience this unique city is with a custom-made Sheffield vacation package. Stay in the neighborhood of Canann Village Historic District, which is great for dining, culture and shopping or go someplace else — our package deals are all about you. Fill your free time with visits to Ski Butternut, Housatonic River Walk and Lake Buel, some of the things you really should see during a trip to Sheffield. Don't delay exploring this city any longer. Your ultimate Sheffield vacation is only a few clicks away with Expedia.
The Latest Sheffield vacation packages
Price found within the past 48 hours. Click for updated prices.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Save 100% on your flight
Price was $829, price is now $492 per person
$492
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!
Reviewed on Oct 27, 2025
Prospect Berkshires
Save 100% on your flight
Price was $988, price is now $580 per person
$580
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....
Reviewed on Oct 20, 2025
Pocketbook Hotel and Bath
Save 100% on your flight
Price was $815, price is now $556 per person
$556
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in
I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open
Reviewed on Nov 12, 2025
Wilder House Berkshires
Save 100% on your flight
Price was $734, price is now $530 per person
$530
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
19.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!
Reviewed on Nov 10, 2025
Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House
Save 100% on your flight
Price was $1,012, price is now $791 per person
$791
per person
Jan 16 - Jan 19
found 22 hours ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
12/10 Exceptional! (1 review)
The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life.
The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure.
Reviewed on Aug 23, 2025
Discover the most popular places to visit in Sheffield
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.
Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $161 total per night from Nov 25 to Nov 26
$161 total
Nov 25 - Nov 26
Total with taxes and fees
9.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!
Reviewed on Nov 10, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Dec 7 to Dec 8
$110 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (763 reviews)
The room was very clean, appreciated the friendly and helpful staff. Well stocked kitchen, super close to grocery stores and restaurants.
Reviewed on Nov 21, 2025
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $107 total per night from Nov 25 to Nov 26
$107 total
Nov 25 - Nov 26
Total with taxes and fees
9/10 Wonderful! (801 reviews)
Enjoyed the Clubhouse before retiring in for the evening. Cozy, comfortable, and relaxing atmosphere.
Reviewed on Nov 10, 2025
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.
Find the Best Sheffield Vacation Packages
Sheffield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,400 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Bash Bish Falls State Park, Umpachene Falls Park and Mount Everett State Reservation |
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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.