Sheffield Holiday Rentals from NZ$215: Search Short-Term Rentals

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Our top choices for Sheffield holiday rentals

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

22 Sept - 23 Sept

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

2. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

3 Sept - 4 Sept

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

3. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington

Mary R.

includes taxes & fees

8 Sept - 9 Sept

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

4. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

bob i.

includes taxes & fees

7 Sept - 8 Sept

A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

5. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Great Barrington

Rebecca K.

includes taxes & fees

30 Aug - 31 Aug

A sandy beach with a lake and forest in the background.

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Great Barrington

Kristin O.

includes taxes & fees

14 Sept - 15 Sept

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

7. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

8 Sept - 9 Sept

A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

8. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Hillsdale

includes taxes & fees

30 Aug - 31 Aug

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

9. Berkshire Mountain Lodge

Pittsfield

Robert

includes taxes & fees

31 Aug - 1 Sept

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

10. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Peter S.

includes taxes & fees

1 Sept - 2 Sept

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

11. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

includes taxes & fees

30 Aug - 31 Aug

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

12. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

includes taxes & fees

21 Sept - 22 Sept

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

13. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveller

includes taxes & fees

21 Sept - 22 Sept

A hot tub with a string of lights above it, set against a dark night sky.

14. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

includes taxes & fees

7 Sept - 8 Sept

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

15. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

includes taxes & fees

3 Sept - 4 Sept

A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.

16. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted

Steve

includes taxes & fees

1 Sept - 2 Sept

17. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

Otis

includes taxes & fees

7 Sept - 8 Sept

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

18. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

includes taxes & fees

9 Sept - 10 Sept

19. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

30 Aug - 31 Aug

A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

20. stylish Berkshires Retreat

Lee

includes taxes & fees

8 Sept - 9 Sept

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Top Sheffield Hotel Reviews

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."

The Little Lion

8/10 Good

"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."

Find out more about Sheffield

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sheffield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sheffield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sheffield. Seeing all the best attractions is bound to make you fall in love with Sheffield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sheffield short-term rentals, that won’t be hard to do.

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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Sheffield is located near skiing, 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. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Sheffield?

With 23 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, Three Mile Pond Wildlife Management Area and Mount Everett State Reservation 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.

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Check prices for these dates

Our top choices for Sheffield holiday rentals

1. Cheerful 3-bedroom cottage with woodstove

2. Home in Great Barrington

3. Cozy. Clean. Free bagel shop. 3 Fireplaces.

4. Cozy 1-bedroom studio in serene Great Barrington with AC

5. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

6. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

7. Cozy Riverside Berkshires Retreat

8. Fantastic 2-bedroom house with AC in quaint Hillsdale.

9. Berkshire Mountain Lodge

10. Sweet Cozy Victorian in Housatonic. Close to everything.

11. The Brooks Motel: Exceptional Suite

12. Treetop Hideaway in Tyringham

13. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

14. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

15. Stylish Mid-century Modern Berkshires Cape

16. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

17. Quintessential Berkshire Escape - Artist Home, Tucked Away in Nature

18. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

19. The Brooks Motel: Exceptional Suite

20. stylish Berkshires Retreat

Find holiday rentals that suit your style

Top Sheffield Hotel Reviews

The Red Lion Inn

Holiday Inn Club Vacations Oak 'n Spruce Resort

The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

Quality Inn Lee - Lenox South

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Yankee Inn

The Little Lion

Find out more about Sheffield

Frequently asked questions

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