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 availability on Vacation Homes in Sheffield
Compare Vacation Homes in Sheffield with updated reviews, rates, and availability.
Waterview Home in the Berkshires: Near Hiking
Waterview Home in the Berkshires: Near Hiking
9.2 out of 10, Wonderful, (14)
Cozy Retreat on Copake Lake in our Charming Home
Cozy Retreat on Copake Lake in our Charming Home
9.6 out of 10, Exceptional, (32)
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.8 out of 10, Exceptional, (7)
The price is AED 584
AED 1,229 total
includes taxes & fees
30 Jun - 1 Jul
Save an average of 15% on thousands of hotels when you're signed in
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Peaceful Retreat Compound 10 Minutes to Great Barrington!
10.0 out of 10, Exceptional, (11)
The price is AED 4,408
AED 6,794 total
includes taxes & fees
24 Jun - 25 Jun
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
Le Soleil Suite -- Pool and views 10 min. from downtown Hudson
10.0 out of 10, Exceptional, (7)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
10.0 out of 10, Exceptional, (25)
Charming Sharon Dwelling w/ Deck & Fire Pit!
Charming Sharon Dwelling w/ Deck & Fire Pit!
9.6 out of 10, Exceptional, (4)
Beautiful retreat to the woods to enjoy the winter season.
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, (3)
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
10.0 out of 10, Exceptional, (2)
Private Access To Laurel Lake, Enjoy Lake Life
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (6)
Private Cabin On Over 12 Acres Of Woods!
Private Cabin On Over 12 Acres Of Woods!
9.6 out of 10, Exceptional, (4)
The price is AED 2,898
AED 5,054 total
includes taxes & fees
6 Jul - 7 Jul
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
10.0 out of 10, Exceptional, (107)
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
Beautiful, Spacious 5+ Bedroom House on Highland Lake with Spectacular views!
10.0 out of 10, Exceptional, (85)
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
Ranch on 5+ acres & 0.7 mi to GB Main St. Sleeps 10 + Wi-Fi + HOT TUB
10.0 out of 10, Exceptional, (12)
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.
Other property types in Sheffield
Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (22)
The price is AED 797
AED 1,760 total
includes taxes & fees
19 Jun - 20 Jun
Antique Farmhouse Totally Restored
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (80)
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
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 hotelsExpedia verified reviews
5/5 Excellent
Take me back in history
"It was a cute cozy place. Very old but they keep it clean. "
A verified traveler stayed at The Red Lion Inn
Posted 1 day ago
Top Vacation Homes in Other Destinations
More Accommodation Types in Sheffield
- Cottages in Sheffield (88)
- Apartments in Sheffield (46)
- Cabin Rentals in Sheffield (37)
- B&B in Sheffield (33)
- Farmstay in Sheffield (17)
- Motels in Sheffield (15)
- Guest Houses in Sheffield (8)
- Condo Rentals in Sheffield (6)
- Inns in Sheffield (6)
- Villas in Sheffield (6)
- Aparthotels in Sheffield (3)
- Chalets in Sheffield (3)
- Resorts in Sheffield (3)
- Lodges in Sheffield (3)
- Condo Resorts in Sheffield (1)
- Hotels (1,134)