Search Vacation Homes in Sheffield
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 400 Vacation Homes in Sheffield with updated reviews, rates, and availability.

Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (211)

Remodeled Lakefront retreat!! Come join us for Ski Season!!
Remodeled Lakefront retreat!! Come join us for Ski Season!!
9.6 out of 10, Exceptional, (5)

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
10.0 out of 10, Exceptional, (119)

Heart of Lenox Walk to Town Cozy Cottage!
Heart of Lenox Walk to Town Cozy Cottage!
10.0 out of 10, Exceptional, (68)

Spectacular views and close to Great Barrington.
Spectacular views and close to Great Barrington.
10.0 out of 10, Exceptional, (1)

Enjoy comfortable elegance in this secluded grand home located in town
Enjoy comfortable elegance in this secluded grand home located in town
10.0 out of 10, Exceptional, (65)

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
10.0 out of 10, Exceptional, (45)

Home in Great Barrington
Home in Great Barrington
9.6 out of 10, Exceptional, (19)
The price is AED 735
AED 1,136 total
includes taxes & fees
13 Apr - 14 Apr
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Sheffield

Antique Farmhouse Totally Restored
Antique Farmhouse Totally Restored
9.8 out of 10, Exceptional, (86)

Guesthouse Cabin vacation rentals in Berkshire County
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (5)
The price is AED 1,855
AED 3,188 total
includes taxes & fees
17 Mar - 18 Mar

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
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.
Recent reviews of Sheffield hotels
Recent reviews of Sheffield hotels

The Yankee, Trademark Collection by Wyndham
5/5 Excellent
Great Stay After or Before Shredding the Gnar!
"We came to shred the gnar at the Bousquet ski area down the block. This property is extremely convenient for such an endeavor. Check in was easy. There was exquisite artwork depicting the authentic Berkshire skiing experience in the room. The breakfast was radical. Eggs and sausages and muffins and pastries and excellent coffee. Only issue was that upon arrival we learned that the hot tub and pool were closed for renovations. This was quite unfortunate as we were excited to take some laps in the pool and rejuvenate our tired bodies in the hot tub after a day of shredding so much gnar. "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 2 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Vacation Homes in Other Destinations
More Accommodation Types in Sheffield
- Cottages in Sheffield
- Apartments in Sheffield
- Cabin Rentals in Sheffield
- B&B in Sheffield
- Farmstay in Sheffield
- Motels in Sheffield
- Guest Houses in Sheffield
- Condo Rentals in Sheffield
- Resorts in Sheffield
- Inns in Sheffield
- Villas in Sheffield
- Chalets in Sheffield
- Aparthotels in Sheffield
- Lodges in Sheffield
- Condo Resorts in Sheffield
- Hotels