Sheffield Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Sheffield, Massachusetts, USA

Wilder House Berkshires
FromZA R4,025 per night
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9.5 (50 Reviews)
5 Bedrooms 11 Guests
Wilder House Berkshires
FromZA R3,529 per night
9.8 (43 Reviews)
1 Bedroom 2 Guests
Little House in the Woods by Evergreen Home
10.0 (34 Reviews)
2 Bedrooms 6 Guests
Water-View Home in the Berkshires
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9.0 (3 Reviews)
3 Bedrooms 6 Guests
Race Brook Lodge
FromZA R3,252 per night
8.4 (31 Reviews)
1 Bedroom 2 Guests
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
10.0 (6 Reviews)
1 Bedroom 2 Guests
South Berkshire Barn Apartment with Stunning Views
10.0 (4 Reviews)
2 Bedrooms 8 Guests
Family Friendly in Sheffield, private yet close to everything!
10.0 (63 Reviews)
4 Bedrooms 10 Guests
Gorgeous Sheffield Home in Heart of Berkshires
10.0 (52 Reviews)
5 Bedrooms 15 Guests
Cheerful 3-bedroom cottage with woodstove
10.0 (42 Reviews)
3 Bedrooms 6 Guests
Peaceful and Private Setting
10.0 (6 Reviews)
3 Bedrooms 6 Guests
Majestic Mountain Side Sheffield/Great Barrington/SKI
10.0 (5 Reviews)
4 Bedrooms 8 Guests
SKI & Explore! NEW Beautiful Berkshires Farmhouse
10.0 (5 Reviews)
4 Bedrooms 8 Guests
Serene Berkshire Artist's House
9.8 (29 Reviews)
3 Bedrooms 6 Guests
Berkshires Walk to Brewery or Distillery with Peloton!
9.8 (8 Reviews)
3 Bedrooms 5 Guests
Water-View Home in the Berkshires
9.6 (26 Reviews)
3 Bedrooms 6 Guests
The Race Mountain House
FromZA R14,348 per night
9.6 (7 Reviews)
4 Bedrooms 12 Guests
Luxury Private Estate in the Berkshires | Whitney by AvantStay
8.6 (14 Reviews)
5 Bedrooms 10 Guests

About Sheffield Vacation Rentals

With more than 41 Sheffield vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Sheffield.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Sheffield, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Sheffield. Places to stay near Sheffield are 1555.72 ft² on average, with prices averaging ZA R7,113 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Sheffield with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Sheffield?

What are the top vacation rentals in Sheffield?

How many Rentbyowner vacation rentals are available in Sheffield?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 41 in the Sheffield area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Sheffield.