Sheffield Holiday Rentals

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Holiday Rentals in Sheffield

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is AU$1,117
includes taxes & fees
26 Oct - 27 Oct
Guesthouse Cabin vacation rentals in Berkshire County

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

Amore Estate - beautiful room with many places to explore and relax in.

9.2 out of 10, Wonderful, (31)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
Amore Estate - beautiful room with many places to explore and relax in.

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,281
includes taxes & fees
21 Oct - 22 Oct
Spacious 5-bedroom house in charming Lee with WiFi

Peace and quiet on the lake

9.6 out of 10, Exceptional, (224)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

The Goshen Glass Chalet

9.6 out of 10, Exceptional, (40)
"The chalet was great. Plenty of room, very cozy and in a very quiet neighborhood community. "
The Goshen Glass Chalet

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (83)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (225)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (11)
"Everything was great...and beautiful!"
The price is AU$630
includes taxes & fees
14 Oct - 15 Oct
The Blue Elm - A Historic Berkshire Cottage

Tranquil Lakeside Escape in the Berkshires

10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape

2.0 out of 10, (1)
"The apartment was cute, but it appears they haven't rented it out before. Safety of the apartment was extremely concerning. The refrigerator did not work and there were three unlocked entrances in the barn that allowed full access to the apartment I was in. I've asked for a partial refund but have not received any confirmation from the owner or VRBO."
Quiet 2BR/1BA Forest-View Barn Apartment – Newly Renovated, Peaceful Escape

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.6 out of 10, Exceptional, (15)
"We came for a concert at Tanglewood. Property was just as photos described, walking distance to downtown Lee restaurants, easy access to highway and other towns. Great spot for multiple family or friends to get together."
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lakefront Fall Foliage in New England Just 2 Hours From NYC

10.0 out of 10, Exceptional, (84)
"Great location and fully equipped cabin! I hope to return sometime soon Everything was perfect!"
Lakefront Fall Foliage in New England Just 2 Hours From NYC

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (68)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (8)
"The house is very sweetly appointed with a comfortable bed, well stocked kitchen, coffee station, and helpful guidebook for the local area. Oriana was very communicative, helpful, and warm. "
Charming cottage with lake access, wood burning fire place, and WiFi

Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.

10.0 out of 10, Exceptional, (25)
"Had a wonderful stay. 10/10, great privacy, amenities, and beautiful view of the lake. Would love to come again!"
Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
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$630 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?

Antique Farmhouse Totally Restored : This highly rated holiday home rental in Sheffield is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Sheffield?

With 25 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 Three Mile Pond Wildlife Management Area 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.