Sheffield holiday lettings

We found 710 holiday rentals — enter your dates for availability

Discover a selection of 24 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.

Holiday rentals with weekly discounts - Sheffield

Showing deals for:17 Oct - 24 Oct
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Why visit Sheffield

  • Outdoor Adventures: Sheffield is perfect for skiing and various outdoor sports, catering to thrill-seekers and nature enthusiasts alike.
  • Picturesque Nature: Explore stunning national parks and nature reserves, offering eco-friendly experiences amidst breathtaking landscapes.
  • Charming History: Discover historical sites that reflect Sheffield’s rich heritage and local culture.
  • Cozy Accommodation: Enjoy delightful stays in holiday cottages that provide comfort and a homely atmosphere.
  • Local Cuisine: Savor the unique flavours of Sheffield at local barbecue spots, ensuring a memorable culinary experience.

Popular types of accommodation in Sheffield

If you're contemplating a getaway to Sheffield, you're in for a treat with our diverse selection of holiday rentals. From charming Sheffield holiday cottages to modern apartments and spacious houses, we have something to suit every traveller's needs. Enjoy the comfort and convenience of Sheffield holiday rentals, ensuring a memorable stay in this vibrant city. Let us help you find the perfect Sheffield holiday home for your next adventure!

  • Houses: The most sought-after choice for holiday accommodation in Sheffield, ideal for families or groups seeking a home-like experience.
  • Cottages: A charming option, these quaint dwellings offer a delightful countryside feel for a relaxing stay.
  • Apartments: Convenient and accessible, apartments provide a comfortable base for exploring Sheffield and its surroundings.
  • Cabins: Perfect for nature lovers, these rustic retreats allow you to immerse yourself in the beautiful landscapes of the area.
  • Condos: A modern choice, condos combine comfort with amenities, catering to those who enjoy a contemporary setting.**

Top attractions in and around Sheffield

Sheffield, Massachusetts, is an ideal destination for those seeking adventure and outdoor activities, particularly skiing and sports. Visitors can explore various attractions such as national parks, nature reserves, and museums, offering eco-friendly experiences. For a delightful stay, consider a holiday cottage break in Sheffield, where you can fully immerse yourself in the natural beauty and local culture.

  • Bash Bish Falls State Park: A stunning natural gem located 4.3km from Sheffield, this park features breathtaking waterfalls and lush scenery, perfect for adventurous outdoor activities and scenic hikes.
  • Ashley House: Situated in Sheffield, this charming museum offers a glimpse into local history and culture, showcasing fascinating exhibits and a warm, inviting atmosphere.
  • Lake Buel: Just 3.7km away, this picturesque lake is ideal for relaxing beach days, romantic picnics, and outdoor adventures amidst serene surroundings.

Things to do recommended for couples

For a romantic getaway in Sheffield, indulge in skiing at Ski Butternut, just 3.1km away. Enjoy a delightful wine tasting at Les Trois Emme Winery, also 3.1km from town. For a musical evening, head to Music Mountain, located 8.1km away, for a memorable concert experience.

Things to do recommended for families

During your family holiday in Sheffield, Massachusetts, you can unwind at Lake Mansfield Park, located 4.3km away, offering a serene atmosphere. Additionally, explore Tyringham Cobble, 7.5km away, where you can enjoy nature and relaxation together as a family.

Things to do recommended for groups

Experience the thrill of motor racing at Lime Rock Park, just 8.1km from Sheffield. Enjoy stunning views while hiking the Housatonic River Walk, located 3.7km away. For an evening of culture, catch a show at the nearby Mahaiwe Performing Arts Center, also 3.7km away.

Booking with Vrbo is simple

Are you hoping to cut costs on your next holiday? Being flexible with your travel dates can be a great way to achieve this, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Where to stay near Sheffield

Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation, making it an ideal destination for those seeking a unique vacation experience. Explore the charming historical sites, enjoy outdoor sports, or unwind by a cosy fireplace. Nearby, discover family-friendly neighbourhoods and picturesque scenery that exude a romantic atmosphere. Don't miss out on the local barbecue spots for a true taste of Sheffield, ensuring a memorable trip filled with friendly people and vibrant vibes.

  • The Berkshires: Nestled approximately 6.8km from Sheffield, The Berkshires is renowned for its stunning outdoor scenery and adventurous spirit. This picturesque region is a haven for those who enjoy skiing, with various ski fields and resorts offering excellent winter sports opportunities. In addition to winter activities, visitors can explore the tranquil lakes and majestic mountains that dot the landscape. The Berkshires also hosts numerous events and conferences, making it a vibrant hub for culture and community engagement.
  • Great Barrington: Located around 3.7km from Sheffield, Great Barrington is a charming city that promises an exhilarating adventure for sports enthusiasts. Known for its excellent skiing facilities, including ski fields and resorts, this area attracts visitors seeking a mix of outdoor sports and leisure. Nearby, you'll find breathtaking lakes and mountains, as well as the beautiful national state park, which offers ample opportunities for hiking and exploring the natural beauty of the region.
  • South Egremont: Just 3.1km from Sheffield, South Egremont is another delightful city that caters to those looking for adventure and sporting activities. Its proximity to ski fields and resorts makes it an appealing destination for winter sports lovers. The surrounding landscape features stunning lakes and mountains, as well as close access to a national state park, providing visitors with endless options for outdoor exploration and relaxation amidst nature's beauty.

Best time to go to Sheffield

If you're planning a trip to Sheffield, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like February and November to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageSlightly Low
February24.8°F (-4.0°C)Light RainMostly CloudySlightly LowAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighAverage
August67.8°F (19.9°C)Light RainMostly SunnyAverageSlightly High
September60.8°F (16.0°C)Light RainMostly SunnySlightly HighAverage
October49.8°F (9.9°C)Light RainMostly SunnyAverageAverage
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowSlightly High
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

What do I need to keep in mind when booking a vacation in 'Sheffield

If you're travelling with a group, family, pets, or planning a longer stay, it’s important to use the right filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Sheffield with a group: Think about how many bedrooms you require, along with additional features like a fully equipped kitchen or outdoor areas for gatherings. Thankfully, you can easily apply filters for all these preferences and more on Vrbo.
  • Traveling to Sheffield with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Sheffield: For many families, a holiday wouldn’t feel complete without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
  • Planning for a long term stay visiting Sheffield: If you’re in search of holiday rentals with savings for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a practical platform for planning your travels, allowing you to create new trips, resume from where you left off, or easily view and organise your arrangements. You can find your saved or booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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:

  • Umpachene Falls Park (4.4 mi / 7.1 km)
  • Ski Butternut (5.3 mi / 8.6 km)
  • Catamount Ski Area (7.4 mi / 12 km)
  • Harney and Sons Tea Tasting Room (9.8 mi / 15.8 km)
  • Lake Taghkanic State Park (17.9 mi / 28.8 km)
  • Mohawk Mountain Ski Area (19.1 mi / 30.8 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:

  • Umpachene Falls Park (4.4 mi / 7.1 km)
  • Lake Buel (5.8 mi / 9.3 km)
  • Housatonic River Walk (6 mi / 9.7 km)
  • Housatonic River (6.1 mi / 9.7 km)
  • Lake Mansfield Park (6.6 mi / 10.6 km)
  • Mount Frissell (9.5 mi / 15.3 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 rental accommodation in Sheffield?
The most popular types of holiday 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 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 rental 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 rentals 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 rentals in Sheffield?
Happily, yes. You'll have your pick of 31 holiday 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 holiday 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 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 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 holiday home that fits your style with all the features you're looking for.
Are there large group holiday 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 holidays to events like birthday parties and weddings, Vrbo will help you find a large group rental to match the occasion.
Are there holiday rentals 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 rentals 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 rentals with WiFi in Sheffield?
You can pick from 12 holiday 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 holiday rentals 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.
How old do you have to be to rent a holiday rental in Sheffield?
We recommend you check with the Sheffield holiday rental you're looking at on Vrbo as the age limit varies. However, typically it's 16, 18 or 21.
How long can I rent a holiday rental in Sheffield for?
The amount of time you can book a Sheffield holiday home for depends on each property. Just enter your travel dates to see available options that offer extended stays. They have everything you need to make your extended trip more convenient and enjoyable, like kitchens and yards. Some holiday homes may also offer weekly or monthly discounts, so you can hang around longer for less.

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