Sheffield Hotels

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Sheffield hotels

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (16)
"Room was very cozy and beautiful. Brad was very helpful and pleasant. The breakfast was delicious. We had a great getaway. Thank you. "
The price is P8,575
P9,578 total
includes taxes & fees
Mar 9 - Mar 10
Wilder House Berkshires

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (98)
"So charming, friendly staff, perfectly comfortable. We had the best stay. "
The price is P9,502
P10,927 total
includes taxes & fees
Mar 6 - Mar 7
Blackberry River Inn

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (119)
"Absolutely a wonderful experience. It was just what i was looking for. Truly unique, very comfortable, surrounded by beauty and nature. Gracious host. Win, win. We will be back."
The price is P14,396
P17,695 total
includes taxes & fees
Feb 27 - Feb 28
Gedney Farm

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (82)
"2nd stay here, even nicer than the first (and the first was amazing!). Can’t wait to return to this enchanting inn! "
The price is P15,321
P18,488 total
includes taxes & fees
Feb 27 - Feb 28
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (375)
"The host Heidi was friendly and fun to talk with at breakfast (I was travelling alone). She knows a lot about the area and history which was nice to hear. The house was quiet and clean and I'd stay here again."
The price is P6,071
P6,981 total
includes taxes & fees
Feb 27 - Feb 28
Locust Tree Bed and Breakfast LLC

Hitching Post Country Motel

2.5 star property
6.0 out of 10, (41)
"Motel says it all. "
The price is P7,516
P8,643 total
includes taxes & fees
Feb 27 - Feb 28
Hitching Post Country Motel

Pilgrim Inn

2.5 star property
5.8 out of 10, (303)
"room was clean heater was noisy bed was too soft pillow mattress no shampoo dont think they checked on our room after 1st night no coffee, cups room 101"
The price is P3,998
P4,465 total
includes taxes & fees
Feb 27 - Feb 28
Pilgrim Inn

Quality Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Nice place. Made fresh waffle mix when I asked. No complaints"
The price is P4,865
P5,434 total
includes taxes & fees
Mar 16 - Mar 17
Quality Inn

Sunset Inn

2.0 star property
7.6 out of 10, Good, (379)
"I think some of the unfavorable reviews I have seen are unfair. Everything is relative and, yes, this is clearly an older property that appears to be privately owned. Notwithstanding its age and some of the dated decor and furnishing, my room was very clean (cleaner than some I have stayed in at upscale hotels). It was one of the coldest nights of the year and the heat worked well and the water was hot. The television and WiFi worked and for my purposes (a one night layover on my way to visit...
The price is P4,625
P5,166 total
includes taxes & fees
Mar 1 - Mar 2
Sunset Inn

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is P10,984
P12,270 total
includes taxes & fees
Feb 27 - Feb 28
Chambery Inn

Econo Lodge Lee - Great Barrington

2.0 star property
6.2 out of 10, (585)
"It was close to Butternut on a snowy day. Very good for the value and what it is."
The price is P3,469
P3,875 total
includes taxes & fees
Feb 27 - Feb 28
Econo Lodge Lee - Great Barrington

Cornwall Inn and Lodge

3.0 star property
9.2 out of 10, Wonderful, (130)
"A charming spot by the river. A bit rustic, but very comfortable and clean and the host is attentive and friendly. Pretty much what you would expect..."
The price is P11,505
P13,231 total
includes taxes & fees
Feb 27 - Feb 28
Cornwall Inn and Lodge

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is P14,396
P16,080 total
includes taxes & fees
Mar 4 - Mar 5
Devonfield Inn B&B

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (999)
"Two adults and a baby to enjoy winter wonderland: it worked very well! Very close to everything! "
The price is P5,848
P6,532 total
includes taxes & fees
Mar 6 - Mar 7
The Black Swan Lee - Lenox, Ascend Hotel Collection

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

3.5 star property
9.0 out of 10, Wonderful, (600)
"Great family vacation"
The price is P6,880
P8,492 total
includes taxes & fees
Mar 2 - Mar 3
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (247)
"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."
The price is P7,285
P8,544 total
includes taxes & fees
Feb 28 - Mar 1
Lakehouse Inn

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is P8,279
P9,248 total
includes taxes & fees
Feb 27 - Feb 28
The Ponds at Foxhollow

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (628)
"Very clean and comfortable with great restaurant and bar downstairs"
The price is P7,554
P8,438 total
includes taxes & fees
Mar 2 - Mar 3
Hilton Garden Inn Lenox Pittsfield

Wagon Wheel Inn

2.0 star property
7.2 out of 10, Good, (600)
"Great location. Pleasant staff."
The price is P3,989
P4,456 total
includes taxes & fees
Feb 27 - Feb 28
Wagon Wheel Inn

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (713)
"spacious room. "
The price is P4,567
P5,102 total
includes taxes & fees
Feb 27 - Feb 28
Howard Johnson by Wyndham Lenox
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.
Don't see what you're looking for?
See all available properties in Sheffield
Save an average of 15% on thousands of hotels when you're signed in

Learn more about Sheffield

Love casinos and history? Get away to Sheffield!

Frequently asked questions

Where is the best place to stay in Sheffield?

Wilder House Berkshires is a favorite with Expedia customers. This B&B offers free breakfast and free parking. Race Brook Lodge is another top choice for your trip based on traveler reviews. See all available top hotels, or 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?

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires: Offers 2 indoor pools, 2 outdoor pools, and 2 restaurants. 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 29 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 Housatonic River and Mount Everett State Reservation exemplify the area's natural beauty. A couple of additional sights to add to your agenda are Magnolia Bluffs Casino and Ashley House. 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.