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May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

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Top 10 Sheffield hotels and places to stay

33 Main
Luxury Room, 1 King Bed, Bathtub
33 Main
4.0 star property
10.0 out of 10, Exceptional, (62)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is CA $486
CA $543 total
includes taxes & fees
May 13 - May 14
33 Main
Lakehouse Inn
Aerial view
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (152)
"The Lakehouse Inn is really cute, right on a lake with wonderful waterfront spaces. The bathroom situation is more European--toilet and shower in the bathroom, sink outside. There was no tub, not a problem for me but good to be aware of. The morning breakfast was delicious! I was greeted with a white wine sangria. It's conveniently located for roaming around Stockbridge, Great Barrington, etc. Close to the Norman Rockwell museum, Hancock Shaker Village, Edith Wharton estate. Would absolutely...
The price is CA $185
CA $216 total
includes taxes & fees
May 14 - May 15
Lakehouse Inn
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is CA $294
CA $329 total
includes taxes & fees
May 19 - May 20
Chambery Inn
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Blackberry River Inn
Library
Blackberry River Inn
3.0 star property
9.6 out of 10, Exceptional, (26)
"Lucas was very accommodating and helpful. Pleasant and great place to stay. Great fresh breakfast!!"
The price is CA $248
CA $285 total
includes taxes & fees
May 30 - May 31
Blackberry River Inn
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (382)
"This is a lovely place to say. Very warm and welcoming. The staff was very helpful and even brought a little doggy basket for my dog. It included a blanket, dog bowls treats and more!! Had a very very nice time. "
The price is CA $198
CA $217 total
includes taxes & fees
May 13 - May 14
Shaker Mill Inn
The Barrington
Junior Suite
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (95)
"Great stay, the room was as advertised, delicious breakfast included and great location. Will stay again. "
The price is CA $444
CA $496 total
includes taxes & fees
May 13 - May 14
The Barrington
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (134)
"This is a charming and very pleasant place to stay."
The price is CA $194
CA $217 total
includes taxes & fees
May 17 - May 18
Brook Farm Inn
Race Brook Lodge
Exterior
Race Brook Lodge
2.0 star property
9.4 out of 10, Exceptional, (8)
"It was quiet setting by the rooms are run down "
The price is CA $182
CA $204 total
includes taxes & fees
Jun 4 - Jun 5
Race Brook Lodge
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Reception
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (646)
"Employees were excellent. Very nice location to stay. Pool was nice and well kept "
The price is CA $208
CA $232 total
includes taxes & fees
May 27 - May 28
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior
The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1003)
"Even though it’s an older hotel I would definitely stay here again because of the service and location. Well appointed rooms and nice small lake area and common areas. The staff were so helpful and friendly- even found us a great place to walk!"
The price is CA $138
CA $154 total
includes taxes & fees
May 19 - May 20
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (463)
"Very clean and commodious. It felt like a home away from home. It might feel dated to some but we found it very luxurious for the price. We didn’t really take advantage of many of the amenities but they are ample. The kitchen was well stocked with everything needed. I would definitely come back."
The price is CA $190
CA $226 total
includes taxes & fees
May 14 - May 15
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (590)
"Great overnight stay. Cleanest place ever. "
The price is CA $91
CA $102 total
includes taxes & fees
May 16 - May 17
Monument Mountain Motel
Locust Tree Bed and Breakfast LLC
Miscellaneous
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (321)
"Great B&B … everything is easy, clean, friendly owners, great breakfast! "
The price is CA $144
CA $165 total
includes taxes & fees
May 13 - May 14
Locust Tree Bed and Breakfast LLC
Little Cat Lodge
Seasonal outdoor pool
Little Cat Lodge
2.0 star property
9.0 out of 10, Wonderful, (8)
"Booked a weekend stay at Little Cat Lodge for a girlfriends trip. The lodge was very cute and had just about everything we needed. Complimentary breakfast was also much appreciated. 3 women shared a 2-bed bedroom and it was great for size- we loved our little balcony. Would definitely recommend this spot! "
The price is CA $271
CA $292 total
includes taxes & fees
May 13 - May 14
Little Cat Lodge
The Red Lion Inn
Outdoor pool, sun loungers
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (881)
"Great service from the staff and a beautiful place to relax and unwind"
The price is CA $190
CA $243 total
includes taxes & fees
May 21 - May 22
The Red Lion Inn
The Cornell Inn, Lenox
Porch
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1001)
"It was a great place to stay for the night. "
The price is CA $164
CA $192 total
includes taxes & fees
Jun 10 - Jun 11
The Cornell Inn, Lenox
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Standard Room
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (496)
"Really enjoyed the seating outside and pool side was very relaxing. The staff was very helpful and informative. Great experience!!!"
The price is CA $193
CA $215 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
The Briarcliff Motel
Exterior
The Briarcliff Motel
3.0 star property
8.8 out of 10, Excellent, (384)
"We loved this place. It's dog friendly, the place is clean and quiet. The proprietor is awesome. It's super friendly. We spent a total of 9 days here, and I'd definitely come back again. Thanks for a great stay"
The price is CA $150
CA $168 total
includes taxes & fees
May 13 - May 14
The Briarcliff Motel
The Lenox Collection
Front of property
The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (194)
"safe, clean, perfect location. Communicative hosts who ensured that someone would be on location when I arrived late. Continental breakfast was extensive and healthy. Will definitely be visiting again. "
The price is CA $123
CA $138 total
includes taxes & fees
May 27 - May 28
The Lenox Collection
Apple Tree Inn
Seasonal outdoor pool
Apple Tree Inn
3.0 star property
8.2 out of 10, Very good, (212)
"Absolutely gorgeous room. Wonderful staff, I felt like royalty. "
The price is CA $169
CA $212 total
includes taxes & fees
May 23 - May 24
Apple Tree Inn
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Frequently asked questions

Where is the best place to stay in Sheffield?

Race Brook Lodge is one of the top choices for your stay based on our traveler data. This hotel offers 2 bars and a restaurant. Other good choices for your trip to the area are The Red Lion Inn and Life House Berkshires. See all available top hotels, or vacation rentals in Sheffield.

What are some of the best vacation home rentals that Sheffield has to offer?

Peace and quiet on the lake: This vacation home rental outside of Sheffield is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind. See all vacation rentals in Sheffield.

If I need to cancel my hotel reservation in Sheffield, will I receive a refund?

Yes! The majority of hotel room reservations are refundable provided that you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.

Where can I learn more about changing or cancelling my trip to Sheffield?

To access more information about changing or cancelling your trip to Sheffield, go to https://www.expedia.com/service/.

What's the best place to stay near Ashley House?

Sheffield 1802 House is one of the top choices for your stay based on our traveler data, and this 3.5-star B&B offers free breakfast and free parking. It's located 3.2 mi (5.1 km) from Ashley House. Another good option is Locust Tree Bed and Breakfast, located 3.8 mi (6.2 km) away.

What about the best place to stay near Magnolia Bluffs Casino?

One of the top choices for your stay is Sheffield 1802 House, located 1.6 mi (2.6 km) from Magnolia Bluffs Casino, and this 3.5-star B&B offers free breakfast and free parking.

What are some accommodations with pools in Sheffield?

Race Brook Lodge : Features 2 bars, a seasonal outdoor pool, and free self parking. The Red Lion Inn and The Yankee, Trademark Collection by Wyndham are a couple of other choices that offer an onsite pool. View all hotels with pools in Sheffield.

What is the best accommodation for staying close to Albany International Airport (ALB)?

Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.

What's it like staying in Sheffield?

Visitors can enjoy all that Sheffield has to offer including the casinos and local tours. In Sheffield, there are 32 hotels and other accommodations to choose from. Find out more about Sheffield.

What should I see while I'm in Sheffield?

The picturesque setting of Mount Everett State Reservation and Housatonic River exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Magnolia Bluffs Casino and Thom Reed UFO Monument Park. Check out what more to see and do in Expedia's Sheffield guide.

What's the weather like in Sheffield?

The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.