vrbo
Beginning of main content

Search results showing properties in Sheffield, Massachusetts, United States of America

Google map showing 500 properties

Photo gallery for “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Picture yourself, lakefront, on your dock on lovely 150 acre private lake.
House · 1.4 mi (2.2 km) to Sheffield center

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Sleeps 4 · 2 bedrooms · 2 bathrooms
10 out of 10 Exceptional (153 reviews)
The price is $283
avg per night
More information about “Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway, opens in a new tab

Photo gallery for Charming Berkshires Cottage by Evergreen Home

Outdoor deck with screened gazebo
Premier Host
House · 4.1 mi (6.5 km) to Sheffield center

Charming Berkshires Cottage by Evergreen Home

Sleeps 4 · 2 bedrooms · 1+ bathroom
9.6 out of 10 Exceptional (8 reviews)
The price is $195
avg per night
More information about Charming Berkshires Cottage by Evergreen Home, opens in a new tab

Photo gallery for Waterview Home in the Berkshires: Near Hiking

Sheffield Vacation Rental | 3BR | 2BA | 2,262 Sq Ft | 2 Steps to Enter
Premier Host
House · 1.5 mi (2.4 km) to Sheffield center

Waterview Home in the Berkshires: Near Hiking

Sleeps 6 · 3 bedrooms · 2 bathrooms
9.2 out of 10 Wonderful (13 reviews)
The price is $253
avg per night
More information about Waterview Home in the Berkshires: Near Hiking, opens in a new tab
House · 1.6 mi (2.6 km) to Sheffield center

Cheerful 3-bedroom cottage with woodstove

Sleeps 8 · 3 bedrooms · 2+ bathrooms
10 out of 10 Exceptional (21 reviews)
The price is $217
avg per night
More information about Cheerful 3-bedroom cottage with woodstove, opens in a new tab
Apartment · 2.5 mi (3.9 km) to Sheffield center

Built in 1739, near Appalachian Trail & River, 7 Min. from Great Barrington

Sleeps 4 · 2 bedrooms · 1 bathroom
The price is $133
avg per night
More information about Built in 1739, near Appalachian Trail & River, 7 Min. from Great Barrington, opens in a new tab
Cottage · 3.7 mi (6 km) to Sheffield center

The Blue Elm - A Historic Berkshire Cottage

Sleeps 4 · 1 bedroom · 1+ bathroom
10 out of 10 Exceptional (2 reviews)
The price is $250
avg per night
More information about The Blue Elm - A Historic Berkshire Cottage, opens in a new tab
House · 2.9 mi (4.7 km) to Sheffield center

Beautiful Mountainside House with nearby Lake and Hiking Trails

Sleeps 8 · 3 bedrooms · 2 bathrooms
10 out of 10 Exceptional (12 reviews)
The price is $275
avg per night
More information about Beautiful Mountainside House with nearby Lake and Hiking Trails , opens in a new tab
House · 1.2 mi (1.9 km) to Sheffield center

PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music

Sleeps 9 · 3 bedrooms · 2 bathrooms
9.8 out of 10 Exceptional (29 reviews)
The price is $365
avg per night
More information about PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music, opens in a new tab
House · 2.3 mi (3.7 km) to Sheffield center

Family Friendly in Sheffield, private yet close to everything!

Sleeps 10 · 4 bedrooms · 3+ bathrooms
10 out of 10 Exceptional (44 reviews)
The price is $431
avg per night
More information about Family Friendly in Sheffield, private yet close to everything!, opens in a new tab
Cabin · 4.7 mi (7.5 km) to Sheffield center

Guesthouse Cabin vacation rentals in Berkshire County

Sleeps 12 · 4 bedrooms · 2+ bathrooms
10 out of 10 Exceptional (1 review)
The price is $596
avg per night
More information about Guesthouse Cabin vacation rentals in Berkshire County, opens in a new tab
House · 3.5 mi (5.6 km) to Sheffield center

Serene Berkshire Artist's House

Sleeps 6 · 3 bedrooms · 2+ bathrooms
9.8 out of 10 Exceptional (26 reviews)
The price is $284
avg per night
More information about Serene Berkshire Artist's House, opens in a new tab
House · 0.9 mi (1.5 km) to Sheffield center

12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room

Sleeps 12 · 4 bedrooms · 2 bathrooms
10 out of 10 Exceptional (18 reviews)
The price is $385
avg per night
More information about 12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room, opens in a new tab
House · 4.4 mi (7.1 km) to Sheffield center

Spacious & Modern Ashley Falls Home on 1 Acre

Sleeps 8 · 5 bedrooms · 3 bathrooms
10 out of 10 Exceptional (7 reviews)
The price is $430
avg per night
More information about Spacious & Modern Ashley Falls Home on 1 Acre, opens in a new tab
House · 1 mi (1.7 km) to Sheffield center

Open for ski season or full time rental. Book 2024 Summer Season now for less.

Sleeps 2 · 1 bedroom · 1 bathroom
10 out of 10 Exceptional (1 review)
The price is $123
avg per night
More information about Open for ski season or full time rental. Book 2024 Summer Season now for less., opens in a new tab
House · 4.8 mi (7.7 km) to Sheffield center

Antique Farmhouse Totally Restored

Sleeps 16 · 4 bedrooms · 3 bathrooms
10 out of 10 Exceptional (78 reviews)
The price is $483
avg per night
More information about Antique Farmhouse Totally Restored , opens in a new tab
House · 1.3 mi (2.1 km) to Sheffield center

Whitney by AvantStay | Private Berkshires Estate

Sleeps 10 · 5 bedrooms · 2+ bathrooms
8.8 out of 10 Excellent (5 reviews)
The price is $470
avg per night
More information about Whitney by AvantStay | Private Berkshires Estate, opens in a new tab
House · 1.9 mi (3 km) to Sheffield center

Gorgeous Sheffield Home in Heart of Berkshires

Sleeps 15 · 5 bedrooms · 3+ bathrooms
10 out of 10 Exceptional (47 reviews)
The price is $608
avg per night
More information about Gorgeous Sheffield Home in Heart of Berkshires, opens in a new tab
House · 3 mi (4.8 km) to Sheffield center

Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly

Sleeps 9 · 4 bedrooms · 3 bathrooms
10 out of 10 Exceptional (115 reviews)
The price is $839
avg per night
More information about Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly , opens in a new tab
Tell us how we can improve our siteShare feedback