Discover a selection of 480 holiday rentals in Sheffield, MA, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 174 per night, and houses and cottages are popular options for a stay in Sheffield. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Sheffield
Destination guide

The historical city of Sheffield awaits you

Enjoy the history and other features of Sheffield. This city is well-known for its casino gaming and local tours. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.


Activities and attractions in and around Sheffield

Do you want to find top things to see and do while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Sheffield a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Umpachene Falls Park (4.8 mi / 7.7 km)
  • Questing (5.4 mi / 8.7 km)
  • Les Trois Emme Winery (6 mi / 9.7 km)
  • Ski Butternut (6.5 mi / 10.5 km)
  • Land of Nod Vineyard and Winery (6.7 mi / 10.8 km)
  • Dry Hill (7 mi / 11.3 km)
Natural features

Exploring the natural features in Sheffield

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Sheffield. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Umpachene Falls Park (4.8 mi / 7.7 km)
  • Lake Mansfield Park (7.6 mi / 12.2 km)
  • Taconic Trail State Park (8.1 mi / 13 km)
  • Haystack Mountain State Park (10.2 mi / 16.5 km)
  • Beartown State Forest (10.9 mi / 17.6 km)
  • Tyringham Cobble (12.9 mi / 20.7 km)
How to get there

How to get to and around Sheffield

The nearest airport is in Hudson, NY (HCC-Columbia County), located 22.4 mi (36.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.1 mi (37.2 km) away.

How many holiday rentals are available around Sheffield?

Our 2021 accommodation listings offer a large selection of 480 holiday lettings around Sheffield. From 385 houses to 48 cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

Can I rent Houses in Sheffield?

Yes, of course. Vrbo UK offers 385 Houses in Sheffield. Our other popular types of Sheffield holiday rentals include:

  • Cottages: 48 self catering accommodations
  • Cabins: 55 self catering accommodations
  • Flats: 41 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Country houses and more.

Can I find a holiday accommodation with pool in Sheffield?

Yes, you can select your preferred holiday accommodation with pool among our 73 holiday homes with pool available in Sheffield. Please use our search bar to access the selection of holiday rentals available.