Search Vacation Homes in Sheffield

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 400 Vacation Homes in Sheffield with updated reviews, rates, and availability.

Peace and quiet on the lake

9.6 out of 10, Exceptional, (210)
"This was a cozy tucked away location that seemed far away from everything which was exactly what we wanted. The host was extremely communicative before and during the stay. The house had fresh linens and towels as well as basic cleaning supplies. It was cozy for a wintery weekend in. We enjoyed snowshoeing on the frozen lake! Pet-friendly was a huge plus! "
Peace and quiet on the lake

Remodeled Lakefront retreat!! Come join us for Ski Season!!

9.6 out of 10, Exceptional, (5)
"We skied, we played in the snow and overall just relaxed at this perfect home!"
Remodeled Lakefront retreat!! Come join us for Ski Season!!

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (119)
"The property was great for our group of 8. Slept everyone comfortably, with plenty of places to hangout and lounge all together. We had planned to cook in for a couple meals, so it was a hugely pleasant surprise to see that the kitchen was stocked with every cooking utensil, serving dish, and glassware that you could possibly need. We were maybe even more prepared than in my own kitchen at home. Also very well located. Had an excellent stay and would come back!"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (67)
"Tom’s cottage was the perfect place for us to stay to enjoy the new year in quiet Lenox. It was centrally located which made exploring town easy and convenient. The check in and out process was super simple and Tom made himself easily accessible throughout the stay. "
Heart of Lenox Walk to Town Cozy Cottage!

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (65)
"Beautiful home perfect for our multi-generational family. We loved the separate spaces and easy walk to the town center. We can’t wait to come back!"
Enjoy comfortable elegance in this secluded grand home located in town

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (45)
"We had an amazing long ski weekend at the Great Escape Ski Cottage. The listing is very accurate. Great communication with Shay. The house was immaculate upon arrival. The layout of the house was perfect for our family (6 adults and 4 children aged 4-9). One beautiful Master Bedroom on the first floor. Two of the other equally beautiful bedrooms are on the second floor. The linens were hotel quality! The "Kid's Quarters" was located off of the kitchen/laundry room. A playroom with multiple games...
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Home in Great Barrington

9.6 out of 10, Exceptional, (19)
"Our family had a wonderful experience and stay. "
The price is SAR 807
SAR 1,253 total
includes taxes & fees
19 Mar - 20 Mar
Home in Great Barrington

Berkshires Lakefront Retreat

10.0 out of 10, Exceptional, (6)
"Outfitted with everything a guest could want or need, from a fully equipped kitchen, linens, and cozy afghans to marshmallows for the hot chocolate. Spacious house with lots of places to gather or spread out. Beautiful setting—snow covered frozen lake. We would love to return in warm weather to make use of the lakefront. Very responsive and considerate host. "
Berkshires Lakefront Retreat

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Beautiful, remote property perfect for large groups! We'll definitely try get back there in the summer!"
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

10.0 out of 10, Exceptional, (9)
"Our family of six stayed at Lee Manor during the Christmas holidays. The house was a lovely older home with modern amenities. It was very well stocked with all the needs of home. The house was spacious and the beds were very comfortable. We enjoyed the back sitting area with the stove heater for watching movies, playing games in the front room, and gathering in the kitchen for snacking. We had great communication with the owners and the Check-in and Check-out process was flawless. It was a...
Lee Manor Berkshire House for Lasting Memories. 5 Bedrooms. 5 Full Bathrooms.

Mountain View Getaway

10.0 out of 10, Exceptional, (49)
"Such a magical place…always enjoy our stay. The home is so comfy - the hosts are amazing. "
Mountain View Getaway

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (2)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

10.0 out of 10, Exceptional, (1)
Laurel Lake Luxury 4BR, 4.5 Bath, Ranch on Fox Hollow Estate

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"
The price is SAR 634
SAR 1,291 total
includes taxes & fees
11 Mar - 12 Mar
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

10.0 out of 10, Exceptional, (139)
"We had a wonderful trip, the kitchen is fully stocked with tons of kitchen tools, 2 slow cookers, etc! Cooking basics were available, soaps, dishwasher pods etc! The rooms were great! The playroom was amazing for all the kids! We had a wonderful time and will be back! "
Secluded Estate w/ Guest House, Private Pond, Gym, & Movie Theater | Sunny Pond

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.4 out of 10, Exceptional, (40)
"We have stayed here twice and it is a great spot, located a few minute drive north of downtown Lenox. The house is cozy yet spacious and is great for our family to stay in while visiting family in the area. We used the kitchen to cook a meal during one of the stays and we had everything we needed. There is an air hockey table in the basement which the kids enjoyed. The house is on a main road, but it was still easy enough to pull in and out of and the noise of the road did not bother us at all....
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Linden by AvantStay | Countryside Berkshire Escape

9.6 out of 10, Exceptional, (9)
"Our family had a wonderful time staying at Linden House. It was comfortable for the 6 adults and 4 young children. We loved the sophisticated charm of the house with its beautiful artwork and furnishings. It has quality appliances and a fully equipped kitchen. We plan to return next year."
Linden by AvantStay | Countryside Berkshire Escape

Perfect Nature Retreat In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Retreat In Great Barrington

Monterey Home w/ Hot Tub, Pool & Game Room!

9.0 out of 10, Wonderful, (2)
"Beautiful property. Lovely grounds. Clean and so much fun for the little ones. Communication and service were excellent. "
Monterey Home w/ Hot Tub, Pool & Game 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.
Don't see what you're looking for?
See all available properties in Sheffield
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Sheffield

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (86)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is SAR 1,895
SAR 3,252 total
includes taxes & fees
11 Mar - 12 Mar
Guesthouse Cabin vacation rentals in Berkshire County

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.