Sheffield Vacation Rentals from $139: Search Short-Term Rentals

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Our top choices for Sheffield vacation 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.

$465 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

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

Great Barrington

bob i.

$148 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

3. Home in Great Barrington

Great Barrington

HEATHER G.

$364 nightly

Sep 3 - Sep 4

Total with taxes and fees

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

4. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

$172 nightly

Aug 30 - Aug 31

Total with taxes and fees

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

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

Great Barrington

Kristin O.

$315 nightly

Sep 2 - Sep 3

Total with taxes and fees

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

6. Berkshire Mountain Lodge

Pittsfield

Robert

$125 nightly

Aug 31 - Sep 1

Total with taxes and fees

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.

$282 nightly

Sep 8 - Sep 9

Total with taxes and fees

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

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

Housatonic

Peter S.

$286 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

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

Great Barrington

Mary R.

$500 nightly

Sep 8 - Sep 9

Total with taxes and fees

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

10. Real Estate: Therapy - Lake, Laundry, Love it

Sherwood Forest

William C B.

$253 nightly

Sep 13 - Sep 14

Total with taxes and fees

11. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

$181 nightly

Aug 30 - Aug 31

Total with taxes and fees

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

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

Hillsdale

$605 nightly

Aug 30 - Aug 31

Total with taxes and fees

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

13. 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.

$551 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

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

winsted

Steve

$212 nightly

Sep 1 - Sep 2

Total with taxes and fees

15. Cozy Camper tucked into the woods

Sandisfield

$191 nightly

Sep 6 - Sep 7

Total with taxes and fees

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.

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

Sherwood Forest

Sharon K.

$340 nightly

Sep 9 - Sep 10

Total with taxes and fees

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.

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

Great Barrington

Rebecca K.

$1,188 nightly

Aug 30 - Aug 31

Total with taxes and fees

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

18. stylish Berkshires Retreat

Lee

$359 nightly

Sep 14 - Sep 15

Total with taxes and fees

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

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

Sherwood Forest

Frank M.

$355 nightly

Sep 7 - Sep 8

Total with taxes and fees

A loft bedroom with a television, wooden shelves, a ladder, and a skylight.

20. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Winchester

$198 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Sheffield Hotel Reviews

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

Berkshire Mountain Lodge

8/10 Good

"the good….full kitchen, living room, king bedroom, clean bathroom, VERY reasonable nightly rate, especially for central berkshire county in the summer. there is no daily room cleaning, but extra towels, etc are always available from the front desk… the less than good…we’ve stayed here now u time in the past 18 months, but the last couple of stays the rooms have been a little musty and damp, despite (or because of?) the a/c being on constantly. ya gotta hold the handle down on the toilet to get a complete flush. no food service, but the is a stop&shop literally across the street… i would still recommend BML for the room rate and location alone…"

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!"

Find out more about Sheffield

Everything you need to know about Sheffield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sheffield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sheffield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Sheffield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $139 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sheffield rentals

At Expedia, we put the best Sheffield vacation 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 vacation.

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.

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Frequently asked questions

Can I find a vacation rental in Sheffield?

Yes, you can find vacation rentals near popular attractions in Sheffield, or you can select a more secluded option if you'd like a relaxing place to stay. Sheffield is known for its casinos and local tours.

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

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home near Sheffield is located near skiing and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Sheffield?

With 23 Expedia vacation rentals, you're sure 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 vacation rentals like in Sheffield?

Vacation rentals are private accommodations you can stay in for a couple days or more in Sheffield. Vacation rentals feature extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for a family trip.

Sheffield Vacation Rentals

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Check prices for these dates

Our top choices for Sheffield vacation rentals

1. Cheerful 3-bedroom cottage with woodstove

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

3. Home in Great Barrington

4. The Brooks Motel: Exceptional Suite

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

6. Berkshire Mountain Lodge

7. Cozy Riverside Berkshires Retreat

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

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

10. Real Estate: Therapy - Lake, Laundry, Love it

11. The Brooks Motel: Exceptional Suite

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

13. Treetop Hideaway in Tyringham

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

15. Cozy Camper tucked into the woods

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

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

18. stylish Berkshires Retreat

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

20. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Find vacation rentals that suit your style

Top Sheffield Hotel Reviews

Berkshires Untold

Find out more about Sheffield

Explore a world of travel with Expedia

Frequently asked questions

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