Sheffield holiday homes

We found 754 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:18 Dec - 25 Dec

Interior
Terrace/patio
Interior
Exterior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
NZ$4,194
for 7 nights, 1 cottage
NZ$599 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Kitchen open to living room
Kitchen
2nd bedroom
Patio off kitchen
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
NZ$2,799
for 7 nights, 1 cottage
NZ$400 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Dining
The great room with wonderful water views and working fireplace
Open kitchen to great room, wonderful for cooking and entertaining
Sunroom has Queen pull out sofa bed
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
NZ$8,040
for 7 nights, 1 home
NZ$1,149 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Property grounds
Private kitchen
Exterior
Terrace/patio
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
NZ$9,788
for 7 nights, 1 home
NZ$1,398 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Dining Room w/ Doors to Screened Porch Dining Area
Fully screened porch!
Reading nook with natural lighting
Front Staircase
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield

12% off
NZ$6,418
for 7 nights, 1 home
NZ$917 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Dining
Interior
Exterior
Living area
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,707
for 7 nights, 1 cabin
NZ$672 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Outdoor dining and grill on the 16' x 20' wooden deck.
You will love dining and working in this rich and colorful room
Staircase
The living room flows into the dining room.
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
NZ$6,792
for 7 nights, 1 home
NZ$970 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Living area
View from the Top Deck
Approaching the home
Dining Area view
Exceptional
(10 reviews)

Lakefront +pets +skiing +bbq +firepit +games

Copake

8% off
NZ$5,586
for 7 nights, 1 home
NZ$798 per night
includes taxes & fees
Lakefront +pets +skiing +bbq +firepit +games
Living area
Private kitchen
Living area
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Sheffield

8% off
NZ$11,253
for 7 nights, 1 home
NZ$1,608 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Come and unwind.
Porch opens up from dining room. Ceiling fan and lights above.
Game, puzzle and play table - plenty of chairs.
Entrance view.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

New Marlborough

8% off
NZ$3,479
for 7 nights, 1 home
NZ$497 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Second story deck with lake views, dining table for 8, sitting area and grill
Open kitchen area with bar seating, great for socializing while you meal prep.
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open and bright main floor living space with stunning views of Laurel Lake.
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

15% off
NZ$6,778
for 7 nights, 1 home
NZ$968 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Dining
Outdoor dining
Exterior detail
Room
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
NZ$5,045
for 7 nights, 1 home
NZ$721 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Screened in porch
Terrace/patio
Property grounds
Queen bedroom
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
NZ$4,936
for 7 nights, 1 home
NZ$705 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Bathroom
Living area
Private kitchen
Exterior
Wonderful
(36 reviews)

Two Bedroom Cottage Close To Town

Sharon

5% off
NZ$3,914
for 7 nights, 1 cottage
NZ$559 per night
includes taxes & fees
Two Bedroom Cottage Close To Town
Alfresco dining
River view from window
Blue House side entry from driveway
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
NZ$4,792
for 7 nights, 1 home
NZ$685 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Kitchen
Interior
Kitchen
Property grounds
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,737
for 7 nights, 1 home
NZ$962 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Living area
Living area
Terrace/patio
Private kitchen
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
NZ$7,087
for 7 nights, 1 home
NZ$1,012 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
After a hard day on the trails or a long day on the town, relax in this oasis
Never miss a thing with this expansive open concept kitchen and living room
Seamless entertaining with the wide open concept, living room -kitchen- patio
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
NZ$7,988
for 7 nights, 1 home
NZ$1,141 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Private kitchen
Interior
Exterior
Living area
Exceptional
(61 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
NZ$2,028
for 7 nights, 1 apartment
NZ$290 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Lobby
Living area
Living area
Interior
Excellent
(9 reviews)

The Race Mountain House

Sheffield

35% off
NZ$6,729
for 7 nights, 1 home
NZ$961 per night
includes taxes & fees
The Race Mountain House
Property grounds
Property grounds
We highly recommend the Sauna
Interior
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
NZ$4,279
for 7 nights, 1 home
NZ$611 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Private kitchen
Outdoor dining
Living area
Private kitchen
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
NZ$4,878
for 7 nights, 1 home
NZ$697 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Open Living Area
Two Tier Decking with Grill on Lower Deck
Exterior
Room
Exceptional
(14 reviews)

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights

Hillsdale

8% off
NZ$4,640
for 7 nights, 1 home
NZ$663 per night
includes taxes & fees
Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights
Private kitchen
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Open floor plan, natural light in a stylish space
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
NZ$5,849
for 7 nights, 1 home
NZ$836 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home

  • 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)
  • 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)
  • Great Falls (10.1 mi / 16.3 km)
  • Naumkeag Museum (12.6 mi / 20.2 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 Bookabach.
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 Bookabach?
Bookabach 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?
Bookabach 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 Bookabach, 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 Bookabach?
To find Sheffield holiday rentals with free cancellation, just use Bookabach'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, Bookabach 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 Bookabach?
Bookabach'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 Bookabach 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. Bookabach offers something for every taste and budget, from affordable homes in Sheffield to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.