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Top 10 Sheffield hotels and places to stay

The Black Swan Lee - Lenox, Ascend Hotel Collection
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Room was great especially as we were at the back of the hotel and looked out on the lake. Only spoke to one member of staff on arrival. Few eating options as on site Indian restaurant was closed on a Sunday. No lift so ask for ground floor if you can’t carry suitcases upstairs."
The price is CA $192
CA $215 total
includes taxes & fees
Sep 29 - Sep 30
The Black Swan Lee - Lenox, Ascend Hotel Collection
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (991)
"Lovely old hotel with excellent bar and restaurant. Central to all Berkshire sights. Room clean and well-appointed; wonderful shower; lobby and many nooks in which to curl up with drink and a good book… Ambassador felines Jane and Jack make Red Lion Inn feel like home."
The price is CA $309
CA $405 total
includes taxes & fees
Oct 1 - Oct 2
The Red Lion Inn
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
3.5 star property
9.0 out of 10, Wonderful, (530)
"We enjoyed our stay … and were especially grateful for how nice/comfortable our suite was! "
The price is CA $201
CA $240 total
includes taxes & fees
Sep 30 - Oct 1
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
The Constance, The Whitlock, & The Dewey By The Lenox Collection
3.5 star property
8.6 out of 10, Excellent, (361)
"Beautiful location."
The price is CA $187
CA $209 total
includes taxes & fees
Oct 1 - Oct 2
The Constance, The Whitlock, & The Dewey By The Lenox Collection
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1003)
"What a joy this BnB is. Everything is so lovely, from the staff to the overall facilities. It was a true pleasure to stay here. We will be back for sure. "
The price is CA $193
CA $226 total
includes taxes & fees
Oct 2 - Oct 3
The Cornell Inn, Lenox
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (204)
"Great location and service. They really look after you and you have the opportunity to meet other guests in beautiful surroundings "
The price is CA $201
CA $236 total
includes taxes & fees
Sep 29 - Sep 30
Lakehouse Inn
Quality Inn
2.5 star property
8.2 out of 10, Very good, (1004)
"Second floor noisy. could here running water most of the night. Could hear people up stairs."
The price is CA $118
CA $131 total
includes taxes & fees
Oct 27 - Oct 28
Quality Inn
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.2 out of 10, Wonderful, (665)
"Very clean and conveniently located property. The staff were super friendly and helpful."
The price is CA $263
CA $294 total
includes taxes & fees
Oct 1 - Oct 2
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Quality Inn
2.5 star property
8.2 out of 10, Very good, (1000)
"The floors in the bathroom were sticky and the carpet."
The price is CA $139
CA $155 total
includes taxes & fees
Oct 27 - Oct 28
Quality Inn
Blackberry River Inn
3.0 star property
9.4 out of 10, Exceptional, (67)
"Great place to stay for enjoying NW Connecticut activities. Friendly helpful staff, comfortable room, pool, cozy public areas/lobby. The breakfast was delicious in a sunny breakfast room and the servers very gracious about special requests. Am looking forward to future stays here."
The price is CA $213
CA $246 total
includes taxes & fees
Sep 30 - Oct 1
Blackberry River Inn
Little Cat Lodge
2.0 star property
9.0 out of 10, Wonderful, (24)
"I had a lovely stay just in time for the beginning of the fall! The property is surrounded by beautiful mountains, theres a sauna in the property and a zipline walking distance. Theres also a complimentary breakfast in the morning and a coffee machine in your room as well. The customer service was excellent! Mike was amazing and was there to answer any questions at any hour and checked to make sure I was having a nice stay which was greatly appreciated and it really made the stay so much more...
The price is CA $272
CA $294 total
includes taxes & fees
Oct 15 - Oct 16
Little Cat Lodge
Locust Tree Bed and Breakfast LLC
3.0 star property
9.0 out of 10, Wonderful, (349)
"A fantastic Bed and Breakfast! This bed and breakfast is located in a quiet area, close to many natural attractions both in Canaan and surrounding towns. The owners were friendly and personable. "
The price is CA $141
CA $162 total
includes taxes & fees
Oct 14 - Oct 15
Locust Tree Bed and Breakfast LLC
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (559)
"Stay was great except there was no cell service"
The price is CA $87
CA $97 total
includes taxes & fees
Oct 3 - Oct 4
Econo Lodge Lee - Great Barrington
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (503)
"Had a wedding next door and was able to walk to venue, easy check in and out, pleasant owners, bathroom could use some updating otherwise room was comfy and clean"
The price is CA $93
CA $104 total
includes taxes & fees
Oct 27 - Oct 28
Travelodge by Wyndham Great Barrington Berkshires
Monument Mountain Motel
2.5 star property
9.0 out of 10, Wonderful, (653)
"Near restaurants "
The price is CA $115
CA $129 total
includes taxes & fees
Sep 29 - Sep 30
Monument Mountain Motel
The Little Lion
3.0 star property
8.8 out of 10, Excellent, (412)
"Was like walking back in time. Peaceful .If you want coffee in the morning you will need to bring some instant and make in the microwave. "
The price is CA $126
CA $141 total
includes taxes & fees
Oct 27 - Oct 28
The Little Lion
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
2.5 star property
8.8 out of 10, Excellent, (542)
"I liked the many options available for the continental breakfast, the 24 hour tea and coffee bar and the bright clean common areas. The only thing i did not like is the fact that the matresses were very uncomfortable and the pillows too soft."
The price is CA $166
CA $186 total
includes taxes & fees
Sep 29 - Sep 30
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (457)
"Appreciated architecture- downtown lovely"
The price is CA $195
CA $243 total
includes taxes & fees
Oct 10 - Oct 11
Whistler's Inn Bed & Breakfast
Pleasant Valley Motel West Stockbridge
2.0 star property
6.8 out of 10, (945)
"Room is comfortable and clean. Only somewhat annoying issue is we could hear the traffic on Route 90 which is fairly near the facility. "
The price is CA $85
CA $93 total
includes taxes & fees
Oct 3 - Oct 4
Pleasant Valley Motel West Stockbridge
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (146)
"Very charming inn. The staff was very friendly and helpful."
The price is CA $355
CA $396 total
includes taxes & fees
Oct 7 - Oct 8
Brook Farm 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 Life House Berkshires and The Red Lion Inn. See all available top hotels, or vacation rentals in Sheffield.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of Sheffield is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. 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 25 hotels and other accommodations to choose from. Find out more about Sheffield.

What should I see while I'm in Sheffield?

Favorite places to visit include Magnolia Bluffs Casino, Housatonic River, and Thom Reed UFO Monument Park. A couple of additional sights to add to your agenda are Ashley House and Mount Everett State Reservation. 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.