Sheffield Holiday Rentals

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Our top choices for Sheffield holiday rentals

10.0 out of 10, Exceptional, (9 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is AU$1,024
includes taxes & fees
20 Jan - 21 Jan
Guesthouse Cabin vacation rentals in Berkshire County
2.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is AU$526
includes taxes & fees
26 Jan - 27 Jan
Sugar Shack - 300 square feet of pure sweetness.
10.0 out of 10, Exceptional, (9 reviews)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is AU$610
includes taxes & fees
25 Jan - 26 Jan
HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (6 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is AU$537
includes taxes & fees
20 Jan - 21 Jan
BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (3 reviews)
"Happy to have found this lovely place, which is convenient to Tanglewood, pin-drop quiet, and super comfortable. Next time I will avoid VRBO, though, because of its extortionary fees, and book directly with the inn."
United States
jwnyc3
The price is AU$406
includes taxes & fees
25 Jan - 26 Jan
Suite 4 - Quiet and private accommodations in a country setting.
2.5 star property
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is AU$963
includes taxes & fees
22 Jan - 23 Jan
CT Gate House Goshen CT, Gate House Goshen CT
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
9.6 out of 10, Exceptional, (10 reviews)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is AU$577
includes taxes & fees
21 Jan - 22 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is AU$373
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is AU$303
includes taxes & fees
20 Jan - 21 Jan
The Brooks Motel: Exceptional Suite
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is AU$389
includes taxes & fees
1 Feb - 2 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
9.4 out of 10, Exceptional, (3 reviews)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is AU$675
includes taxes & fees
19 Jan - 20 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
2.0 star property
The price is AU$553
includes taxes & fees
29 Jan - 30 Jan
Updated and inviting home in Lenoxdale
9.4 out of 10, Exceptional, (6 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is AU$1,765
includes taxes & fees
18 Feb - 19 Feb
The George is an elegant restored home in the Hudson Valley
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is AU$1,296
includes taxes & fees
19 Jan - 20 Jan
Whispering Estate Guest House - A Romantic Countryside Getaway

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$447
includes taxes & fees
19 Jan - 20 Jan
Family Ski Getaway in the Berkshires
10.0 out of 10, Exceptional, (1 review)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is AU$406
includes taxes & fees
25 Jan - 26 Jan
Suite 3 - Quiet and private accommodations in a country setting.
2.0 star property
The price is AU$453
includes taxes & fees
25 Jan - 26 Jan
Renovated house. Built in 1890s. No neighbors in sight.
8.0 out of 10, Very good, (2 reviews)
"What a darling house! We stayed with my mother and my adult kids for Thanksgiving and it was the perfect spot! The host was most attentive to all of our questions and request ex! It’s the perfect location for visiting the Hudson Valley and the house was so comfortable and accommodating for all of us! We loved everything about it!"
United States
Mary R.
The price is AU$851
includes taxes & fees
19 Jan - 20 Jan
Tranquil Victorian on Charming Street
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheffield Hotel Reviews

Find out more about Sheffield

Everything you need to know about Sheffield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheffield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sheffield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheffield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheffield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheffield holiday rentals we have selected for you start as low as AU$373 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sheffield rentals

At Expedia, we put the best Sheffield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheffield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheffield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheffield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Sheffield?

Yes, there are holiday rentals close to the most popular sights in Sheffield, or you can select a more secluded option if you're looking for a relaxing stay. Sheffield is known for its casinos and local tours.

What are some of the best holiday rentals that Sheffield has to offer?

Peace and quiet on the lake: This holiday home rental outside of Sheffield is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Sheffield?

With 24 Expedia holiday rentals, you're guaranteed to find just the right place for your Sheffield stay.

What’s there to see and do in Sheffield?

Housatonic River and Thom Reed UFO Monument Park are a couple of scenic spots to enjoy the outdoors, whereas Ashley House is one of the cultural attractions. While here, Magnolia Bluffs Casino and Drury Preserve are other places worth a visit.

What are holiday rentals like in Sheffield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sheffield. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for a family getaway.