Sheffield holiday rentals

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your current months are March, 2024 and April, 2024.
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Discover a selection of 27 homes and other holiday rentals in Sheffield that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

The historical 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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Sheffield

Are you looking for attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Sheffield a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 an outdoor enthusiast or just want to spend some time taking in the scenery, Sheffield is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport to and around Sheffield

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Sheffield?

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

How much does it cost to rent a holiday home in Sheffield?

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

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

The average price for a holiday 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 holiday homes in Sheffield?

Happily, yes. You'll have your pick of 31 holiday homes that welcome pets in Sheffield on Vrbo. Our cuddly best friends need a break too, so simply use our search function for pet-friendly holiday homes 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 holiday 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 home amenities in Sheffield?

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

Are there large group holiday homes 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 holidays to events like birthday parties and weddings, Vrbo will help you find a large group home to match the occasion.

Are there holiday homes in Sheffield that welcome kids?

Sheffield has 31 family-friendly holiday 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 holiday 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 holiday homes in Sheffield?

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

Are there holiday homes with WiFi in Sheffield?

You can pick from 12 holiday homes 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 holiday homes with air conditioning in Sheffield?

You'll find 21 holiday 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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