Search Condos in Sheffield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11
In one month
Jan 23 - Jan 25
In two months
Feb 20 - Feb 22
No exact matches found, but these alternatives could be just right

Recommended hotels in Sheffield

Interior detail
Wilder House Berkshires

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (41)
"The place is lovely, room is cozy, and the bed is comfy"
United States
Mark
The price is ￥25,418
￥28,393 total
includes taxes & fees
Dec 30 - Dec 31
Wilder House Berkshires
Interior
Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (9)
"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 ￥61,355
￥107,421 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥37,185
￥78,865 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cheerful 3-bedroom cottage with woodstove
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1006)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ￥14,537
￥16,239 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Yankee, Trademark Collection by Wyndham
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1000)
"My go to place for my ski weekends"
United States
Ryan
The price is ￥11,810
￥13,193 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Quality Inn Great Barrington
Miscellaneous
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1000)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ￥15,737
￥17,578 total
includes taxes & fees
Jan 13 - Jan 14, 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ￥16,393
￥18,852 total
includes taxes & fees
Dec 25 - Dec 26
Locust Tree Bed and Breakfast LLC
Lobby
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ￥21,076
￥23,542 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Element Lenox Berkshires
Desk, laptop workspace, blackout drapes, iron/ironing board
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ￥8,106
￥8,892 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Pleasant Valley Motel West Stockbridge
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (810)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (710)
"Great hospitality "
United States
regina maria
The price is ￥16,788
￥18,752 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
The price is ￥11,709
￥13,080 total
includes taxes & fees
Dec 30 - Dec 31
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, laptop workspace, iron/ironing board
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,333
￥13,776 total
includes taxes & fees
Dec 30 - Dec 31
Howard Johnson by Wyndham Lenox
Check-in/check-out kiosk
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ￥15,407
￥20,697 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Berkshire Mountain Lodge
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1003)
"The staff is always so helpful & nice, and the rooms are always clean and comfortable. This is my favorite place to stay in Lee!"
United States
Cooper
The price is ￥12,899
￥14,408 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quality Inn Lee - Lenox South
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ￥22,595
￥32,249 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Red Lion Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
The price is ￥16,635
￥18,249 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Shaker Mill Inn
Terrace/patio
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ￥19,965
￥22,301 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hilton Garden Inn Lenox Pittsfield
Lobby lounge
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ￥16,318
￥18,227 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn & Suites Berkshires-Lenox
Exterior
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (190)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
The price is ￥21,857
￥24,479 total
includes taxes & fees
Dec 27 - Dec 28
the Alander
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheffield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The room is so spotless, bathroom is so luxurious! The bed is so soft and sleep very quickly! The staffs are so great! Quick to answer to my questions and my needs. Definitely come back again to stay! "
Brandon 3-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Sheffield

Sheffield Condo Rentals information

Number of reviews
12,456
Accommodation
11 Condo Rentals
Lowest Price
￥8,892
Highest Price
￥107,421

Frequently asked questions

Why book your condo in Sheffield with Expedia?
Booking a condo in Sheffield is as simple as clicking on your travel dates and selecting an option that meets your needs. On the lookout for something upscale or budget friendly, or a property that also comes with a pool and a hot tub? Use Expedia's search filters to narrow your results even further and find your perfect match.
How can I find cheap condos in Sheffield?
With Expedia's helpful filter tool, comparing cheap condos in Sheffield is a breeze. To discover properties that'll make your hip pocket happy, narrow down your search by amenities, budget and star rating.
What is there to do in Sheffield near my condo?
After you've unpacked your bags, venture out and explore the awesome things Sheffield has for you to experience. Magnolia Bluffs Casino is a great attraction to add to your must-do list.

Explore a world of travel with Expedia