Book Hotels in Sheffield, MA

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Top Sheffield hotels

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield
$617 nightly
The price is $689 total per night from Sep 28 to Sep 29
$689 total
Sep 28 - Sep 29
Total with taxes and fees
This cabin includes a garden and barbecue grills.
"This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon."

Reviewed on Aug 27, 2025

Opens in a new windowGuesthouse Cabin vacation rentals in Berkshire County
Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $211 total per night from Oct 27 to Oct 28
$211 total
Oct 27 - Oct 28
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 ...
"I always enjoy my stay at Wilder House, thank you!!"

Reviewed on Sep 23, 2025

Opens in a new windowWilder 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
$138 nightly
The price is $154 total per night from Sep 28 to Sep 29
$154 total
Sep 28 - Sep 29
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 ...
"The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area ..."

Reviewed on Sep 22, 2025

Opens in a new windowHoliday 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
$128 nightly
The price is $143 total per night from Sep 29 to Sep 30
$143 total
Sep 29 - Sep 30
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 ...
"Ggg"

Reviewed on Sep 20, 2025

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
$115 nightly
The price is $128 total per night from Oct 27 to Oct 28
$128 total
Oct 27 - Oct 28
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 location. so nice to wake up to the view of the lake and have kayaks on property to rent. within a short drive of everything. staff was very nice and informative. downsides are you can hear everything through the front door. it’s hard to stay quiet enough for your neighbors. also no water pressure ..."

Reviewed on Sep 22, 2025

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
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Sep 28 to Sep 29
$126 total
Sep 28 - Sep 29
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, ...
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again."

Reviewed on Sep 25, 2025

Opens in a new windowBerkshire Mountain Lodge
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
$217 nightly
The price is $243 total per night from Sep 29 to Sep 30
$243 total
Sep 29 - Sep 30
Total with 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 ...
"A great place if you appreciate and like history. The lobby is filled with antiques and the porch is great to rock in a chair and sip some wine. Parking is no issue and you can walk to local restaurants and shops."

Reviewed on Sep 16, 2025

Opens in a new windowThe Red Lion Inn
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$93 nightly
The price is $104 total per night from Oct 9 to Oct 10
$104 total
Oct 9 - Oct 10
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. ...
"Very good"

Reviewed on Sep 22, 2025

Opens in a new windowQuality 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
$79 nightly
The price is $88 total per night from Sep 28 to Sep 29
$88 total
Sep 28 - Sep 29
Total with 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.
"Great place to stay for overnight stays. Breakfast was appreciated."

Reviewed on Sep 15, 2025

Opens in a new windowHoward Johnson by Wyndham Lenox
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See all available properties in Sheffield
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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 $88. 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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

5 out of 5
Posted 20 hours ago
Travelocity Verified Review
"Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. "
A verified traveler from Weymouth stayed at Berkshire Mountain Lodge
Berkshire Mountain Lodge
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