Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Start by selecting your hotel
Start by selecting your hotel

Save up to $603 by booking Flight + Hotel.

Search 590,000 properties and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more


Sheffield

Welcome to Sheffield! Although you won't be getting a look at any of the world's famous attractions here, you'll still have plenty to see and do.

Packages in Sheffield

It is really easy to save with your flight and lodging packages via Expedia. You and your loved ones will have one less thing to be concerned about when you purchase lodging and flight package deals with us. Go on a shopping trip in Sheffield with the extra money.

When you secure a package deal, you'll save as much as $603.

Around 400 partner airlines and 321,000 hotels worldwide are ready for you to book on our enormous global database.

Expedia gives you some of the best prices for your Sheffield adventure.

If you change your plans we will honor your cancellation request with no extra fee from us, on nearly all bookings.

Sheffield Vacation Packages

From Sheffield, it's 40 miles southeast to Hartford and 45 miles northwest to Albany.

Visiting Magnolia Bluffs Casino is a wonderful way to blow off some steam. Remember to call a sitter!

Why don't you stop at two of the most attractive stretches of coastline? Crystal Lake Sandy Beach, 50 miles to the east, and Sandy Point Beach, 60 miles to the south, are top picks.

Put on your comfortable shoes and soak up the serenity of Glendale Falls, located 25 miles from Sheffield. Another option is McLean Game Refuge, which is 30 miles away.

Find out about Sheffield's culture at Ashley House.

When the snow is falling and it's time to hit the slopes, visit Powder Ridge Mountain Park and Resort or Thunder Ridge Ski Resort. From the center of Sheffield, the former is 50 miles and the latter is 40 miles.

Catamount Ski Area and Catamount Aerial Adventure Park are some popular attractions in South Egremont, a locality 5 miles away. Another idea is New Marlborough. It's about 5 miles out of Sheffield, and is the home of Ski Butternut and Dry Hill.

Consider spending some time in Great Barrington, a regional hub just 6 miles to the north of Sheffield. This area offers a range of visitor attractions, including Questing, Les Trois Emme Winery and Housatonic River Walk. Mahaiwe Performing Arts Center and Art et Industrie are also certainly worth stopping at.

Trying traditional food is one of the best ways to learn about an area. So be sure to stop by some of the region's bars, cafés and restaurants.

Visitors are certain to note an abundance of cod and clams, a couple of popular regional ingredients.

Finish with a bang by sampling some frappe, a dreamy dessert.

Being here during the 4th of July will net you a first-hand impression of Independence Day.

When it's time to get your flight homeward, make your way toward the nearest airport. You'll find it 35 miles to the east.

Accommodation in Sheffield

Because there are only limited Expedia hotels in Sheffield itself, you ought to book ahead if you plan on staying the night.

Some of the accommodations that might suit your needs in and around Sheffield are the Windflower Inn and The Egremont Village Inn.


Top Hotel Deals

See all 139 Hotels in Sheffield
$80
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox
3.9
of 5, from 498 reviews
3.0 out of 5.0

Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. Lenox Library and Bousquet Ski Area are also within 3 mi (5 km).

$114
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

70 Pittsfield Rd, Lenox
4.5
of 5, from 48 reviews
3.5 out of 5.0

Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded Age Museum and Shakespeare and Company are also within 3 mi (5 km).

$101
Hampton Inn & Suites Berkshires Lenox

Hampton Inn & Suites Berkshires Lenox

445 Pittsfield Rd, Lenox
4.6
of 5, from 354 reviews
3.0 out of 5.0

Situated in a rural location, this hotel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary and Canoe Meadows Wildlife Sanctuary are also within 3 mi (5 km).

$136
The Red Lion Inn

The Red Lion Inn

30 Main Street, Stockbridge
4.3
of 5, from 169 reviews
4.0 out of 5.0

This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival, and Naumkeag. Berkshire Botanical Garden and National Shrine of the Divine Mercy are also within 3 mi (5 km).

$79
Days Inn Great Barrington

Days Inn Great Barrington

372 Main Street, Great Barrington
3.8
of 5, from 392 reviews
2.5 out of 5.0

Situated in Great Barrington, this motel is within 1 mi (2 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. W.E.B. Du Bois Boyhood Homesite is 2 mi (3.2 km) away.

$119
Cranwell Spa and Golf Resort

Cranwell Spa and Golf Resort

55 Lee Road, Lenox
4.2
of 5, from 110 reviews
3.5 out of 5.0

Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company and Wood's Pond are also within 3 mi (5 km).

$43
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

42 Stockbridge Rd, West Stockbridge
3.4
of 5, from 591 reviews
2.5 out of 5.0

Situated near the beach, this motel is 2.4 mi (3.8 km) from Berkshire Botanical Garden and within 6 mi (10 km) of Norman Rockwell Museum and Naumkeag. National Shrine of the Divine Mercy and Mission House are also within 6 mi (10 km).

$76
Black Swan Inn, an Ascend Collection Hotel

Black Swan Inn, an Ascend Collection Hotel

435 Laurel St, Lee
4.1
of 5, from 389 reviews
3.5 out of 5.0

Situated on a lake, this hotel is within 1 mi (2 km) of Animagic Museum of Animation and Lee Library. Greenock Country Club and The Mount are also within 3 mi (5 km).

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.