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Top Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
$178 nightly
The price is $199 total per night from Jun 23 to Jun 24
$199 total
Jun 23 - Jun 24
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 ...
"Great stay and the breakfast was fantastic"

Reviewed on Jun 6, 2026

Opens in a new windowWilder House Berkshires
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Fully refundable
$135 nightly
The price is $151 total per night from Jun 14 to Jun 15
$151 total
Jun 14 - Jun 15
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy ...
"Room was very clean and staff went far a beyond to accommodate my husbands needs."

Reviewed on Jun 9, 2026

Opens in a new windowHoliday Inn Express & Suites Pittsfield - Berkshires by IHG
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from Jun 11 to Jun 12
$124 total
Jun 11 - Jun 12
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. ...
"I got the impression that Yankee Inn has quite a history, although it has been recently updated and renovated. The staff were available and friendly. At times I felt I was on a 1950s movie set, imagining Bing Crosby singing in my head. I ultimately extended my stay because it's location was a hub ..."

Reviewed on Jun 8, 2026

Opens in a new windowThe Yankee Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Fully refundable
$144 nightly
The price is $161 total per night from Jun 11 to Jun 12
$161 total
Jun 11 - Jun 12
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 ...
"Spacious well-equipped units. Staff was friendly and helpful. Activity center was very nice. Would definitely stay again"

Reviewed on May 28, 2026

Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3 out of 5
435 Laurel St Lee MA
$130 nightly
The price is $145 total per night from Jun 16 to Jun 17
$145 total
Jun 16 - Jun 17
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 ...
"Great! Loved the stay there!"

Reviewed on Jun 8, 2026

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$149 nightly
The price is $166 total per night from Jul 8 to Jul 9
$166 total
Jul 8 - Jul 9
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, ...
"rented for 2 nights. Apt was clean and climate control worked as expected. Nicely equipped location is good."

Reviewed on Jun 9, 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Jun 10 to Jun 11
$133 total
Jun 10 - Jun 11
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 ...
"The hotel was beautiful. My room was very nice exactly what I needed. The decor was very inviting and the bathroom was amazingly beautiful as well as the lounge and grounds of the property. My only one wish was that there was coffee in the room. Although you just had to walk to the lobby to get coffee ..."

Reviewed on Jun 8, 2026

Opens in a new windowBerkshires Untold
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
$191 nightly
The price is $213 total per night from Jul 8 to Jul 9
$213 total
Jul 8 - Jul 9
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 ...
"It is a charming, historic hotel. Dinner in the tavern was delicious and service was very good. The only thing we didn't like was the mattress, which needs to be replaced as it has divits. Other than that, it's a cool place that is fun to explore. Wish we were here longer to try out the pool. We ..."

Reviewed on Jun 8, 2026

Opens in a new windowThe Red Lion Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$94 nightly
The price is $105 total per night from Jun 14 to Jun 15
$105 total
Jun 14 - Jun 15
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. ...
"Excellent location, great low price, VERY Comfortable bed- throwback era motel. Why pay more when it’s all here!"

Reviewed on Jun 7, 2026

Opens in a new windowQuality Inn Great Barrington
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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.

Sheffield Hotel & Travel Guide\n

Searching for accommodation in the heart of Sheffield? Sheffield lists 3 hotels and apartments, all within an easy commute to the town center.

Found within driving distance of Sheffield, are the The Egremont Village Inn and Locust Tree Bed and Breakfast.

14 miles (23 kilometers) away from the center of Sheffield, you will find the Rock Hall Luxe Lodging. Alternatively, the Rookwood Inn is situated 18 miles (30 kilometers) away. Alternatively, you may wish to make a booking at the Gateways Inn & Restaurant or the Hampton Terrace Inn.

While you are in Sheffield, be sure to visit more of what Western Massachusetts has to offer. Check out Western Massachusetts's history museums and you can also enjoy the region's mountains. Intrepid visitors may involve themselves in skiing here.

30 miles (51 kilometers) to the north of Sheffield, you will reach Lanesborough, which is home to Mount Greylock State Reservation Visitor Center and Skyline Country Club. When you want to spend a night or two in Lanesborough, be sure to check out the The Weathervane Motel and Lanesborough Country Inn. Or, you could stay in Williamstown, 40 miles (64 kilometers) to the north of Sheffield, where you can pick from the The Spring's Inn and Berkshire Hills Country Inn. The Williams College and Williams College Museum of Art are some more frequented attractions to experience for those visiting Williamstown.

Just because you are far from home, doesn't have to mean you shouldn't expand your love of a day watching sports. You will find Times Union Center 45 miles (69 kilometers) to the northwest of Sheffield. For visitors who would like the convenience of checking in to a room close to the game, book a room in the Hilton Albany or TownePlace Suites by Marriott Albany Downtown/Medical Center.

If you're traveling through Bradley International Airport and are hoping to find somewhere to stay in the area, why not consider Sheraton Hartford Hotel at Bradley Airport or Holiday Inn Express & Suites Bradley Airport.

Frequently asked questions

What are the top kid-friendly hotels in Sheffield?
Take some of the troubles out of traveling with little ones by staying in a family-friendly hotel in Sheffield. From fun amenities to extra-helpful services, these stays feature perks that'll make your trip run smoothly: Your entourage will enjoy their time at Berkshire Getaway Walk to Winery, Brewery or Distillery with Peloton!. A playground and animal viewing activities are among the things that help make this property a favorite. Winter in the Berkshires- warm and loved 3 bedroom home is another top place to stay. After a big day of exploring, return to your comfy room and perks like pet-friendly facilities and internet access.
Where can I find cheap hotels in Sheffield?
At Travelocity you'll find really nice hotels in Sheffield at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Sheffield rather than in Sheffield. We may find you even better rates, too.
How do I find the best Sheffield hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Sheffield then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Sheffield?
The cheapest hotel in Sheffield is $105. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Sheffield?
There are 1,296 hotels in Sheffield on Travelocity.
What are the best hotels in Sheffield?
Sheffield has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Sheffield for you!
When is the best time to visit Sheffield?
If you want the joy of a fun-filled trip in peak season, visit Sheffield during February, March and May. If you'd prefer the peace of off-season, book a stay during quieter months, such as October, November and December.
When is the cheapest time to stay in Sheffield?
Based on historic data is usually the cheapest month to visit Sheffield. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Sheffield?
There are multiple hotels in Sheffield that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Sheffield. We have plenty of kid-friendly hotels in Sheffield to choose from on Travelocity!
Why book a hotel in Sheffield through Travelocity?
Because we have the top hotels in Sheffield! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Sheffield on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Sheffield hotel reviews by fellow wanderers

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Room was very clean and staff went far a beyond to accommodate my husbands needs."
A verified traveler stayed at Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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