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Top Sheffield hotels

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $201 total per night from Jun 22 to Jun 23
$201 total
Jun 22 - Jun 23
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
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and childcare is an added bonus. Limo/town ...
"This is our third visit to the farmhouse in Sheffield and we plan to be back again if it’s available. The house has everything you could possibly need or want with lots of space and an outstanding fully equipped kitchen Robin, our host makes it easy for us to wanna come back."

Reviewed on Jun 2, 2026

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Opens in a new windowAntique Farmhouse Totally Restored
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 ...
"I spilled an ENTIRE cup of cocoa I was making for my niece. The clerk on was a very kind, friendly young man named Paul. I have worked as a chef for 30 years, the cocoa went EVERYWHERE. He got a mop bucket , I started cleaning my mess up I just know what its like to walk into a mess!! Left by someone ..."

Reviewed on Jun 1, 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
$105 nightly
The price is $117 total per night from Jun 9 to Jun 10
$117 total
Jun 9 - Jun 10
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. ...
"Everything was really great. Except the only issue my wife and I had was, we reserved a room for a queen size bed and instead received a full size bed. It wasn’t a big deal. But after the stay we realized the queen would’ve been a better way. However, I never brought this matter to the front desks ..."

Reviewed on Jun 7, 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
$152 nightly
The price is $169 total per night from Jun 10 to Jun 11
$169 total
Jun 10 - Jun 11
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
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $166 total per night from Jul 7 to Jul 8
$166 total
Jul 7 - Jul 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, ...
"Very spacious and a good spot if you like to cook for yourself. Decor is dated but it's clean and good value."

Reviewed on Jun 7, 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 9 to Jun 10
$133 total
Jun 9 - Jun 10
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 room was very nice, but a little small. The biggest issue we had is the room was VERY dark. One desk lamp had 2 lights, that one was fine. On the table between the beds there was a tiny lamp with a sort of orange colored very dim bulb. Quite useless. There was a floor lamp in the corner that ..."

Reviewed on Jun 7, 2026

Opens in a new windowBerkshires Untold
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
Fully refundable
$131 nightly
The price is $146 total per night from Jun 16 to Jun 17
$146 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 ...
"Very convenient on lovely lakeside and easy access to route 90 and towns like Lennox and Lee. Decor old fashioned and dull. Mint the Indian food restaurant is excellent, well priced and full of flavour."

Reviewed on Jun 7, 2026

Opens in a new windowThe Black Swan Lee - Lenox, an Ascend Collection Hotel
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $205 total per night from Jun 9 to Jun 10
$205 total
Jun 9 - Jun 10
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 ...
"Ideal location if one is looking to stay in Stockbridge. The guest house we stayed in was quiet and comfortable. But our room was looking a little worn and in need of some updates, such as the carpet. The property has an excellent restaurant. The property was undergoing a renovation during our stay, ..."

Reviewed on Jun 6, 2026

Opens in a new windowThe Red Lion Inn
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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 $117. 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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

4 out of 5
Posted 4 hours ago
Travelocity Verified Review
"Very spacious and a good spot if you like to cook for yourself. Decor is dated but it's clean and good value."
A verified traveler stayed at Berkshire Mountain Lodge
Berkshire Mountain Lodge

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