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Condo Rentals in Sheffield

Peaceful 1BR Condo with Pond View
Steps lead down to the tranquil lake's edge, surrounded by trees and shrubs.

Peaceful 1BR Condo with Pond View

8.0 out of 10, Very Good, (1)
"The location was very close to Tanglewood and The Mount, but the front drive off the main road was really dark, no street lights, so we missed our turn a few times but did eventually find the place. The community was pretty and tranquil, we did not hear any noise at all. The WiFi was a little wonky but no big deal because we were able to get cell service. "
Peaceful 1BR Condo with Pond View
Perfect for Winter Skiing!!
Kitchen features a microwave, oven, refrigerator, coffee maker, toaster, sink, and countertop with a fruit basket.

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
Tranquil Lakeside Escape in the Berkshires
Escape to a serene lakeside haven surrounded by lush greenery and tranquil waters.

Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Enjoy cooking in this fully equipped kitchen with a dining area.

Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood

10.0 out of 10, Exceptional, (2)
"It is located near everything"
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
Spacious 4-bedroom condo with AC and WiFi in Litchfield County
Enjoy al fresco dining on the deck, surrounded by a forest view, with a barbecue grill nearby.

Spacious 4-bedroom condo with AC and WiFi in Litchfield County

Spacious 4-bedroom condo with AC and WiFi in Litchfield County
Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Cozy living area with a fireplace and comfortable seating.

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025
Microwave, oven, stovetop

Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025

Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025
Cozy Condo with resort amenities
Enjoy a peaceful retreat on this balcony with a serene view of lush greenery, featuring two Adirondack chairs and a small table.

Cozy Condo with resort amenities

Cozy Condo with resort amenities
Cozy Condo, walk to town, private and bright
Enjoy meals at the dining table with striped chairs, surrounded by a well-equipped kitchen with a refrigerator, cabinets, and kitchen island.

Cozy Condo, walk to town, private and bright

Cozy Condo, walk to town, private and bright
Condo with Resort Amenities in Lenox
Escape to a serene lakeside haven with steps leading down to the water's edge.

Condo with Resort Amenities in Lenox

Condo with Resort Amenities in Lenox
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Very comfy, stylish and convenient!"
Linda 2-night trip
Posted 7 hours ago
Berkshires Untold

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.