Sheffield holiday rentals

We found 749 holiday rentals — enter your dates for availability
Discover a selection of 23 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:29 Jan - 5 Feb

Image gallery for Guesthouse Cabin vacation rentals in Berkshire County

Interior
10 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
Price is AU$8,610
for 7 nights, 1 cabin
AU$1,230 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County

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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)
  • Otis Ridge (14.3 mi / 23 km)
  • Wyndhurst Golf & Club (16.7 mi / 26.9 km)
  • Lake Taghkanic State Park (17.9 mi / 28.8 km)
  • Mohawk Mountain Ski Area (19.1 mi / 30.7 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:

  • 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)
  • Great Falls (10.1 mi / 16.3 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 best area to stay in Sheffield when booking a holiday rental?
When considering a holiday rental in Sheffield, Massachusetts, the charming neighbourhood of Sheffield Village stands out as a delightful option. This area is known for its picturesque landscapes and historic architecture, providing a lovely backdrop for a relaxing getaway. Visitors can enjoy the scenic beauty of the nearby Berkshire Hills and explore the lush greenery surrounding the village. A popular attraction in the vicinity is the Norman Rockwell Museum, which showcases the celebrated artist's work and offers insight into his life and times. Additionally, the nearby Appalachian Trail provides excellent opportunities for hiking and outdoor activities, making it a great spot for nature enthusiasts.

Another appealing area is the quaint neighbourhood of Ashley Falls, which offers a serene atmosphere and easy access to local amenities. Here, you can take in the tranquil views and perhaps even visit the nearby Berkshire Botanical Garden, which features stunning floral displays and peaceful walking paths. Sheffield boasts a range of holiday rental properties, from cosy cottages to spacious homes, ensuring that there is something to suit various preferences and group sizes.
Where are the best Sheffield ski resort rentals?
For the best ski resort rentals near Sheffield, Massachusetts, travellers should consider the nearby areas of Great Barrington and Butternut Basin. Great Barrington is a charming town that offers a variety of holiday accommodations, including cosy cabins and modern condos. Many of these properties come equipped with amenities such as fully stocked kitchens, fireplaces, and outdoor spaces, ideal for warming up after a day on the slopes.

Butternut Basin, just a short drive from Sheffield, features ski-in, ski-out lodgings that provide direct access to the ski area. Rentals here often include spacious living areas and ski storage facilities, making it convenient for families and groups. Some properties also boast additional features like hot tubs or saunas, superb for relaxation after an active day.

The surrounding Berkshires region is known for its stunning winter scenery, and rentals in nearby towns often offer access to local dining and shopping, enhancing the overall experience. Additionally, outdoor enthusiasts can enjoy various winter activities, including cross-country skiing and snowshoeing, with rentals typically providing easy access to nearby trails.
What is the most popular type of holiday rental accomodation in Sheffield?
In Sheffield, holiday houses are the predominant type of holiday rental, with about 92 available in various scenic spots around the area. These homes typically provide ample space, featuring multiple bedrooms, fully equipped kitchens, and outdoor areas that allow guests to enjoy the tranquil surroundings. Additionally, there are around 12 apartments available, which offer a more compact and convenient option for travellers looking for a simpler stay. Several cottages and cabins can also be found, providing a rustic and charming atmosphere for those wanting a unique getaway experience.
Are there any family house rentals in Sheffield?
In Sheffield, Massachusetts, there are plenty of family-friendly house rentals available—specifically around 22 options for visitors to consider. The area is known for its charming rural landscape, making it an ideal getaway for families seeking both relaxation and adventure. Many of these homes offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.

The nearby attractions include the picturesque Berkshire mountains, where families can enjoy hiking, biking, and stunning views. Additionally, the town is close to various recreational activities such as swimming at local lakes and visiting quaint shops and eateries.
Can I rent a holiday home with a pool or hot tub in Sheffield?
In Sheffield, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque town, located in the Berkshires, provides a serene setting for relaxation and outdoor activities. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor areas, making them ideal for families or groups looking to unwind.

Travellers can also expect amenities such as fully equipped kitchens for self-catering, comfortable living spaces, and often scenic views of the surrounding landscape.
Are there pet-friendly house rentals in Sheffield?
In Sheffield, Massachusetts, there are several pet-friendly house rentals available, with a total of 17 options to choose from. The area is known for its charming rural setting, making it a great spot for families and groups looking to enjoy a peaceful getaway with their pets. Many of these holiday rentals come equipped with amenities such as fully furnished kitchens, spacious living areas, and outdoor spaces where pets can roam freely.

The town itself boasts beautiful surroundings, including nearby parks and nature reserves that welcome pets. For those who enjoy outdoor activities, the Appalachian Trail and the picturesque Berkshire Mountains offer ample opportunities for hiking and exploration with furry companions.
Are there any remote work holiday rentals in Sheffield?
In Sheffield, Massachusetts, there are numerous remote work-friendly holiday rentals available, with around 100 options to choose from. This picturesque town, surrounded by the scenic beauty of the Berkshires, provides an excellent backdrop for those looking to combine work and leisure. Many properties feature dedicated workspaces, free Wi-Fi access in both rooms and public areas, and comfortable environments conducive to productivity.

Travellers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Sheffield?
In Sheffield, popular holiday rental amenities typically include kitchens, allowing guests to prepare their own meals and enjoy home-cooked dining. Many properties also feature decks or patios, which provide a lovely outdoor space for relaxation and enjoying the fresh air. For added comfort, some rentals come equipped with fireplaces, superb for cosy evenings after a day of exploring the area. Additionally, a blender is often available for those looking to whip up smoothies or other blended drinks. Onsite parking is also a common amenity, making it convenient for guests travelling by car.
When is the best time to visit Sheffield for a holiday rental?
The best time to visit Sheffield for a holiday rental is during the peak season from June to August, with July being particularly popular among travellers. This vibrant period is great for those who enjoy outdoor activities, as the warm summer weather creates a friendly space for exploring the beautiful Berkshires. Temperatures typically range from the mid-teens to low 30s Celsius, ideal for hiking, biking, and enjoying local festivals.

In July, Sheffield becomes a hub of activity, with visitors drawn to its picturesque landscapes and charming small-town vibe. Whether you're wandering through scenic parks or indulging in farm-to-table dining experiences, the area offers a wealth of opportunities to immerse yourself in nature and culture.

For those seeking a more budget-friendly option, consider visiting in December, when the holiday spirit fills the air. This month provides a quieter experience, allowing you to appreciate the serene beauty of the winter landscape while enjoying seasonal festivities and local events.

Ultimately, your choice of when to visit Sheffield will depend on whether you prefer the lively summer atmosphere filled with outdoor adventures or the peaceful charm of wintertime exploration.
What are the top attractions in Sheffield?
In Sheffield, Massachusetts, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural charm. The picturesque town is surrounded by the scenic landscapes of the Berkshires, making it ideal for outdoor enthusiasts. Nearby, the Appalachian Trail offers excellent hiking opportunities, while the beautiful lakes and rivers in the region are superb for activities like fishing, kayaking, and swimming.

The quaint downtown area of Sheffield features local shops and eateries, providing a taste of the community's flavour. Additionally, the Norman Rockwell Museum in nearby Stockbridge celebrates the works of the famed illustrator, showcasing art that resonates with many visitors. For those interested in history, the historic homes and buildings throughout the town offer a glimpse into its rich past. The nearby Berkshire Botanical Garden also presents a serene environment for leisurely strolls among beautiful flora.
Are all fees included in the Sheffield holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Sheffield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sheffield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Sheffield holiday homes?
You can find great discounts on holiday homes in Sheffield on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Sheffield holiday home booking on Stayz?
To find Sheffield holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Sheffield?
A long-stay holiday home in Sheffield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Sheffield holiday home?
Book your Sheffield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Sheffield?
Prices for holiday homes in Sheffield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Sheffield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.