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Top Sheffield hotels

Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield
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 ...
Beautiful farmhouse
"We thoroughly enjoyed our stay and would definitely rent this home again. The house is spacious and well-suited for family time, hosting, or just relaxing. It’s furnished with a lot of historical details and ephemera which was charming and helps make the home a really interesting place to stay. One ..."

Reviewed on Jun 20, 2025

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Antique Farmhouse Totally Restored
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
$225 nightly
The price is $251 total per night from Jul 27 to Jul 28
$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 ...
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
$151 nightly
The price is $169 total per night from Jul 30 to Jul 31
$169 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 ...
Enjoyed our stay.
"Our family stay was very nice. We took advantage of the large outdoor pool and the mini golf on site. The property is in a very beautiful woodsy minimally developed area. The unit was fine but not great. The cabinets are generally old looking and water-moisture damaged. All was workable but 5 star ..."

Reviewed on Jul 23, 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 $222 total per night from Jul 27 to Jul 28
$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 ...
"We enjoyed the unique character and flavor of the hotel!"

Reviewed on Jul 19, 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
$135 nightly
The price is $151 total per night from Jul 30 to Jul 31
$151 total
Jul 30 - Jul 31
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 ...
"Loved the outdoor flowers, friendly staff, balconies and water in lobby. Disliked weak shower and very noisy air conditioning. Also entrance to property needs better lighting, more than just the overhead sign."

Reviewed on Jul 22, 2025

The Yankee, Trademark Collection by Wyndham
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 30 to Jul 31
$135 total
Jul 30 - Jul 31
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, ...
"Spacious, convenient to Tanglewood, restaurants, shopping"

Reviewed on Jul 20, 2025

Berkshire Mountain Lodge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
$236 nightly
The price is $264 total per night from Aug 12 to Aug 13
$264 total
Aug 12 - Aug 13
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 ...
"Miranda at the front desk was beyond accommodating. My mom and I enjoyed our stay in this historic hotel!"

Reviewed on Jul 21, 2025

The Red Lion Inn
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
$185 nightly
The price is $206 total per night from Aug 13 to Aug 14
$206 total
Aug 13 - Aug 14
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 ...
"Easy walk to town. Plenty of restaurants available."

Reviewed on Jul 22, 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 Aug 6 to Aug 7
$113 total
Aug 6 - Aug 7
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. ...
"We stayed for two nights at this property while visiting the Tanglewood area. The location is walking distance to restaurants, across the street from a great local brewery, and a short drive to Tanglewood and other area attractions. The room was clean, the beds were comfy and the nightly rate was ..."

Reviewed on Jul 21, 2025

Quality 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 $113. 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 1,250 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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Loved the property, room was clean and had everything you needed!! We had an upgrade that was wonderful!! Only downfall was the outside little deck! No privacy all out In the open, side by side and facing the other units with a walkway in front of it!! Was looking forward to sitting out side but ended up not using it at all. "
A verified traveler stayed at 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
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