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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
$225 nightly
The price is $251 total per night from Jul 21 to Jul 22
$251 total
Jul 21 - Jul 22
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 ...
Lovely stay
"Brad was a terrific host in a perfect location to explore northwestern Connecticut and the Berkshires."

Reviewed on Jun 16, 2025

Wilder House Berkshires
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 refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Jul 16 to Jul 17
$170 total
Jul 16 - Jul 17
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 ...
"Rooms need renovation but a nice property"

Reviewed on Jul 11, 2025

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

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $223 total per night from Jul 14 to Jul 15
$223 total
Jul 14 - Jul 15
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 ...
"I’ve stayed at this property several times including before it changed management. We have always enjoyed everything about it. My only strong suggestion is that there is better signage out by the highway. You do not see the hotel or the sign until you get very close to the turn and it is a very busy ..."

Reviewed on Jul 10, 2025

Berkshires Untold
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Jul 24 to Jul 25
$141 total
Jul 24 - Jul 25
Total includes 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 ...
Great location for Tanglewood
"Friendly staff, clean rooms and a very nice breakfast buffet. Staff went out f their way to help locate and ship two items that I had left behind."

Reviewed on Jul 10, 2025

The Yankee, Trademark Collection by Wyndham
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
$226 nightly
The price is $253 total per night from Aug 6 to Aug 7
$253 total
Aug 6 - Aug 7
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 ...
Weekend getaway
"Very relaxing and extremely relaxing place"

Reviewed on Jun 29, 2025

The Red Lion Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $135 total per night from Jul 14 to Jul 15
$135 total
Jul 14 - Jul 15
Total includes taxes and fees
This lodge features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and ...
"Great area, very reasonable."

Reviewed on Jul 11, 2025

Berkshire Mountain Lodge
The Constance by the Lenox Collection

The Constance by the Lenox Collection

3.5 out of 5
11 Old Stockbridge Road, P.O.Box 1717, Lenox, MA
$178 nightly
The price is $199 total per night from Jul 22 to Jul 23
$199 total
Jul 22 - Jul 23
Total includes taxes and fees
A gym, free self parking, and concierge services are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public ...
"Very convenient and walkable to downtown Lenox, plus there's a free EV charger at the property. The inn is old but charming -- i.e., the library with its wood paneling, its out-of-tune grand piano, and the orange upholstered furniture; definitely feels like staying at an inn during a different age! ..."

Reviewed on Jul 9, 2025

The Constance by the Lenox Collection
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $113 total per night from Jul 27 to Jul 28
$113 total
Jul 27 - Jul 28
Total includes 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. ...
"Easy check in with friendly staff. Super convenient to Mohaiwe Performing Arts, only a five minute walk. Very safe and quiet area."

Reviewed on Jul 13, 2025

Quality Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2 out of 5
462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $111 total per night from Jul 14 to Jul 15
$111 total
Jul 14 - Jul 15
Total includes taxes and fees
An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A garden and express check-out are also provided.
Good value
"Great location for a concert at Tanglewood. Rooms were newly renovated. Very clean"

Reviewed on Jul 11, 2025

Howard Johnson by Wyndham Lenox
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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 $111. 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 1,258 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.

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