Sheffield Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Sheffield holiday rentals

Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 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 HK$3,126
HK$5,490 total
includes taxes & fees
22 Feb - 23 Feb
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,852
HK$3,945 total
includes taxes & fees
8 Mar - 9 Mar
Cheerful 3-bedroom cottage with woodstove
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 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 HK$1,563
HK$2,618 total
includes taxes & fees
9 Mar - 10 Mar
BLUSH: Boutique TINY home*private spa*walk to town
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
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 HK$1,563
HK$2,618 total
includes taxes & fees
2 Mar - 3 Mar
Sugar Shack - 300 square feet of pure sweetness.
Fridge, microwave, oven, stovetop

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9 reviews)
"Loved our stay! Beautiful place and the hosts were very nice. Thank you!"
United States
Kate C.
The price is HK$1,758
HK$3,225 total
includes taxes & fees
24 Feb - 25 Feb
HunnyHAUS: Deluxe TINY*private spa*walk to town
Smart TV, books

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Sherwood Forest
9.8 out of 10, Exceptional, (12 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is HK$1,252
HK$3,083 total
includes taxes & fees
23 Feb - 24 Feb
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
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 HK$830
HK$5,026 total
includes taxes & fees
26 Feb - 27 Feb
CT Gate House Goshen CT, Gate House Goshen CT
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,242
HK$1,567 total
includes taxes & fees
1 Mar - 2 Mar
The Brooks Motel: Exceptional Suite
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 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 HK$1,259
HK$2,096 total
includes taxes & fees
2 Mar - 3 Mar
Home in Great Barrington
Interior

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.0 out of 10, Wonderful, (11 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,495
HK$2,342 total
includes taxes & fees
6 Mar - 7 Mar
Family Ski Getaway in the Berkshires
Exterior

Dugway Hideaway Walking Distance to Lime Rock Park

Dugway Hideaway Walking Distance to Lime Rock Park
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great communication and Super location if you are going to the track. Love my stay there, will definitely do it again and definitely recommend."
United States
Brig
The price is HK$1,563
HK$2,438 total
includes taxes & fees
3 Mar - 4 Mar
Dugway Hideaway Walking Distance to Lime Rock Park
Property grounds

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
8.0 out of 10, Very good, (1 review)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is HK$1,367
HK$2,424 total
includes taxes & fees
23 Feb - 24 Feb
Renovated house. Built in 1890s. No neighbors in sight.
Interior

Suite 1 - Quiet and private accommodations in a country setting.

Suite 1 - Quiet and private accommodations in a country setting.
Spencertown
7.4 out of 10, Good, (3 reviews)
"Modest property, handy to Tangelwood and local attractions Good value. "
United States
Richard S.
Suite 1 - Quiet and private accommodations in a country setting.
Exterior

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

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,337
HK$5,080 total
includes taxes & fees
23 Feb - 24 Feb
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge

Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Cornwall
10.0 out of 10, Exceptional, (5 reviews)
"This cabin is so cute we had a relaxing time , will return"
United States
Candice S.
The price is HK$2,451
HK$4,379 total
includes taxes & fees
23 Feb - 24 Feb
Peaceful Cabin with Sauna, Hot Tub & Cold Plunge
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
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 HK$1,055
HK$2,095 total
includes taxes & fees
23 Feb - 24 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
Interior

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is HK$2,618
HK$4,901 total
includes taxes & fees
23 Feb - 24 Feb
Luxury Barn Retreat — All-Season Escape Awaits!
Smart TV, books

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is HK$1,407
HK$3,596 total
includes taxes & fees
1 Mar - 2 Mar
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Exterior

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills

Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
Goshen
10.0 out of 10, Exceptional, (1 review)
"Without a doubt, we will be back! Your home was so beautiful, warm and comfortable. Our host was so helpful and friendly. We can't thank you enough for providing such a wonderful experience to our trip. "
United States
Linda D.
The price is HK$2,071
HK$4,671 total
includes taxes & fees
27 Feb - 28 Feb
Sequoia House Charming Goshen Getaway – Quiet Retreat in Litchfield Hills
TV, fireplace, printers

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is HK$4,445
HK$10,411 total
includes taxes & fees
24 Feb - 25 Feb
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great location, amenities, pool and hot tub for the kids, friendly staff, comfortable room."
Jennifer 2-night trip
Posted 19 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Sheffield

Search for holiday rentals in Sheffield on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheffield using one of the methods below:

  • View our selection of featured holiday rentals in Sheffield
  • Use the map to find apartments and other holiday homes in the Sheffield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheffield while they last

Look no further and take a look at our great range of rental properties in Sheffield!

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, Lime Kiln Farm Wildlife Sanctuary and Magnolia Bluffs Casino 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.