Sheffield vacation rentals

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your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 27 homes and other vacation rentals in Sheffield that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll have the amenities you expect and more, such as WiFi and cable TV. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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The historic area of Sheffield awaits your stay

Enjoy the history and other features of Sheffield. This city is well-known for its casino gaming and local tours. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Sheffield

Do you want to discover top things to see and do in the city? Venture out of your vacation home and experience everything that makes Sheffield a fun place to get away. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Ski Butternut (5.3 mi / 8.6 km)
  • Catamount Ski Area (7.4 mi / 12 km)
  • Lake Taghkanic State Park (17.9 mi / 28.8 km)
  • Mohawk Mountain Ski Area (19.1 mi / 30.8 km)
  • Otis Ridge (14.3 mi / 23 km)
  • Wyndhurst Golf & Club (16.7 mi / 26.9 km)

Exploring the natural landscape of Sheffield

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Sheffield. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Housatonic River Walk (6 mi / 9.7 km)
  • Bash Bish Falls State Park (7 mi / 11.2 km)
  • Taconic State Park (8.3 mi / 13.3 km)
  • Naumkeag Museum (12.6 mi / 20.2 km)
  • The Mount (16 mi / 25.8 km)
  • Otis Reservoir (16.3 mi / 26.3 km)

Transportation to and around Sheffield

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 22 mi (35.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Sheffield?

The most popular types of vacation rentals in Sheffield are houses. Searching for something different? Vrbo offers a variety of options to match our guests' diverse needs, so you'll see vacation properties in all shapes and sizes. The perfect fit is waiting for you — book yours today.

How much does it cost to rent a vacation rental in Sheffield?

Property type, length of stay and season are some of the conditions that can determine the price of a vacation home. Simply click on your dates of travel to find your ideal fit. From quaint country cottages to sprawling luxury villas, all Vrbo vacation rentals provide amazing value.

How much does it cost to rent a beach house in Sheffield?

The average price for a vacation home by the beach in Sheffield depends on when you'll be there and the size and style of property you want. Find prices easily and quickly on Vrbo by entering your dates of travel. Then use our handy filter tool to pick the number of bedrooms and amenities important to you, such as WiFi, a pool and air conditioning.

Are there pet-friendly vacation rentals in Sheffield?

Happily, yes. You'll have your pick of 31 vacation rentals that welcome pets in Sheffield on Vrbo. Our cuddly best friends need a break too, so simply use our search function for pet-friendly vacation rentals to find a perfect pad where your puppy dog can lap up the fun.

Can I rent a house with a pool in Sheffield?

Add an extra layer of fun to your vacation by staying in one of the seven houses with a private pool in Sheffield. Use our search filter to find properties with pools on Vrbo, then spend your days splashing and playing in a swimming pool that's only for you.

What are popular rental amenities in Sheffield?

Mountain views, a sauna and a lake view are the most popular rental amenities in Sheffield. Whether you plan to travel solo, with your significant other or a group of friends, Vrbo can help you find a vacation home that fits your style with all the features you're looking for.

Are there large group vacation rentals in Sheffield?

With six properties that can sleep 10 or more guests in Sheffield, you won't have to limit the invite list. From fun family vacations to events like birthday parties and weddings, Vrbo will help you find a large group rental to match the occasion.

Are there vacation rentals in Sheffield that welcome kids?

Sheffield has 31 family-friendly vacation homes to choose from. And discovering a stay that welcomes little ones is easy with Vrbo's "Properties good for families" filter. On top of having the entire place to yourselves, you'll have access to perks and conveniences like living rooms, full kitchens and yards.

What are the top attractions for families in Sheffield?

Keeping the kiddos entertained during your Sheffield vacation is a breeze with these fabulous family-friendly attractions:

  • Umpachene Falls Park
  • Bash Bish Falls State Park
  • Housatonic River Walk

Can I find two-bedroom vacation rentals in Sheffield?

Sheffield has four two-bedroom vacation properties to select from. Go for a vacation home with all the privacy and comfort you want at a fantastic price on Vrbo.

Are there vacation rentals with WiFi in Sheffield?

You can pick from 12 vacation rentals with WiFi in Sheffield. If you'd like to disconnect from daily life on your trip, but still want to be connected to the web, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Sheffield?

You'll find 21 vacation homes with air conditioning in Sheffield offering that cooling breeze and extra touch of comfort. Simply enter your travel dates and then use our handy filter tool to help you find properties with air conditioning.

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