Sheffield Hotels from €65 - Fully Refundable Options

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Our top choices for Sheffield hotels

Breakfast included

Wilder House Berkshires

Sheffield

Jennifer

includes taxes & fees

19 Jul - 20 Jul

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

Lenox

Michael

includes taxes & fees

13 Jul - 14 Jul

Locust Tree Bed and Breakfast LLC

East Canaan

Larry

includes taxes & fees

18 Jul - 19 Jul

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pittsfield

Courtney

includes taxes & fees

16 Jul - 17 Jul

Pleasant Valley Motel West Stockbridge

West Stockbridge

Peter

includes taxes & fees

13 Jul - 14 Jul

The Little Lion

Great Barrington

Mia

includes taxes & fees

14 Jul - 15 Jul

Berkshire Travel Lodge

Austerlitz

Kyle

includes taxes & fees

13 Jul - 14 Jul

Hideaway Inn Lenox

Lenox

Leonardo

includes taxes & fees

13 Jul - 14 Jul

the Alander

Copake

includes taxes & fees

15 Jul - 16 Jul

Chatham Travel Lodge

Old Chatham

Jurij

includes taxes & fees

13 Jul - 14 Jul

Monument Mountain Motel

Great Barrington

Yekaterina

includes taxes & fees

13 Jul - 14 Jul

Quality Inn Great Barrington

Great Barrington

sarah

includes taxes & fees

11 Aug - 12 Aug

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Lenox

Luciane

includes taxes & fees

13 Jul - 14 Jul

Blackberry River Inn

Norfolk

Maura

includes taxes & fees

14 Jul - 15 Jul

Little Cat Lodge

Copake Falls

Berenger

includes taxes & fees

16 Jul - 17 Jul

Sunset Inn

Lee

Jay

includes taxes & fees

20 Jul - 21 Jul

The Red Lion Inn

Stockbridge

Allen

includes taxes & fees

22 Jul - 23 Jul

Berkshire Mountain Lodge

Pittsfield

Dalila

includes taxes & fees

11 Aug - 12 Aug

Shaker Mill Inn

West Stockbridge

Mervin

includes taxes & fees

13 Jul - 14 Jul

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Stay near popular Sheffield attractions

Bartholomew's Cobble

10.0/10 (1 review)

This National Natural Landmark features twin rocky knolls and North America's most diverse fern collection. Explore its trails through varied ecosystems while watching for peregrine falcons and rare plants.

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Learn more about Sheffield

Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green.

See all hotels in Sheffield

A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Exceptional accommodation and facility perfect stay."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I found the staff very helpful, especially the young man who worked over night. We experienced a slight problem, and he could not have been nicer. He represented the hotel extremely well. Breakfast was uninspiring but generally good. The view from the breakfast room is lovely. The common areas seem a little tired, but the room was very good value - especially as we overlooked the lake. The location is wonderful for Lee, Lenox, Stockbridge, all the cultural centers and the Mass Pike. A beach is adjacent for swimming. We plan to return next year."

Wilder House Berkshires

10/10 Excellent

"This b&b was so charming. The room was very well kept and had a private bathroom and we especially loved the decor of the living areas. It was well thought out and visually pleasing and calming. Brad the owner was so helpful with suggesting places to eat around the area and Laura the innkeeper made the best breakfasts that were included with our stay. She was very attentive to our needs and even added a nice touch of complimentary champagne for our anniversary. So thoughtful!! We highly recommend this b&b!! The area was so cute with cute towns nearby to explore. And antique shops especially!! Thank you for a wonderful experience!!!"

Quality Inn Lee - Lenox South

10/10 Excellent

"Everything was absolutely what we needed and perfect! My only dislike was when we checked in. I just feel if you are the r to great guests and welcome them then you should and give the details of breakfast and just shoe some hospitality is all. The checkout staff was absolutely awesome! I would stay again as this is a great location."

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

10/10 Excellent

"Always love going to Oak n Spruce. The 2 bedroom delux with 2 king beds and near the small pool is the best. It's quiet and so relaxing. Love going to the gym and game room. So convenient to Lee Premium Outlets on rainy days."

More cheap stays in Sheffield

Quality Inn Great Barrington

372 Main Street Great Barrington MA

€116

11 Aug - 12 Aug

includes taxes & fees

8.6/10 Excellent! (1,015 reviews)

Frequently asked questions

Where is the best place to stay in Sheffield?

Wilder House Berkshires is one of the top choices for your stay based on our traveller data. This B&B offers free breakfast and free parking. Two other options for your trip to the area are The Yankee Inn and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Sheffield.

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

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Sheffield is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 reservations are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it may still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Sheffield.

What are some accommodation options with pools in Sheffield?

The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and The Red Lion Inn are a couple of other choices that feature an on-site pool. View all hotels with pools in Sheffield.

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 accommodation options to choose from. Find out more about Sheffield.

What are the top places to visit in Sheffield?

Favourite places to visit include Housatonic River, Magnolia Bluffs Casino and Bartholomew's Cobble. A couple of additional sights to add to your itinerary are Mount Everett State Reservation and Thom Reed UFO Monument Park. Take a look at what more there is to see and do in Expedia's Sheffield guide.

What's the seasonal weather like in Sheffield?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Sheffield are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Sheffield Hotels

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Our top choices for Sheffield hotels

Wilder House Berkshires

The Yankee Inn

Locust Tree Bed and Breakfast LLC

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pleasant Valley Motel West Stockbridge

The Little Lion

Berkshire Travel Lodge

Hideaway Inn Lenox

the Alander

Chatham Travel Lodge

Monument Mountain Motel

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

Blackberry River Inn

Little Cat Lodge

Sunset Inn

The Red Lion Inn

Berkshire Mountain Lodge

Shaker Mill Inn

Stay near popular Sheffield attractions

Bartholomew's Cobble

Learn more about Sheffield

Top Sheffield Hotel Reviews

Berkshire Mountain Lodge

More cheap stays in Sheffield

Quality Inn Great Barrington

Frequently asked questions

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