We're sorry, some parts of the Savvy website don't work properly without JavaScript enabled.

Find places to stay in Sheffield

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Sheffield Vacation Rentals

Sheffield Vacation Rentals

Find places to stay in Sheffield

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Stop overpaying for
vacation rentals.

Trending stays in Sheffield

Ashley Falls Home w/ Fire Pit: Hike & Ski!

House in Sheffield, MA

Hosted by Evolve

Mar 30 – Apr 4

Ashley Falls Home w/ Fire Pit: Hike & Ski!

House in Sheffield, MA

Hosted by Evolve

Mar 30 – Apr 4

52-Acre Berkshires Farmhouse • Fire Pit, Outdoor Dining + Trails | Copper Kettle Farm by AvantStay

House in Sheffield, MA

Hosted by AvantStay

Mar 19 – Mar 24

52-Acre Berkshires Farmhouse • Fire Pit, Outdoor Dining + Trails | Copper Kettle Farm by AvantStay

House in Sheffield, MA

Hosted by AvantStay

Mar 19 – Mar 24

Whitney by AvantStay | Private Berkshires Estate

House in Sheffield, MA

Hosted by AvantStay

Mar 29 – Apr 3

Whitney by AvantStay | Private Berkshires Estate

House in Sheffield, MA

Hosted by AvantStay

Mar 29 – Apr 3

2% savings

Water-View Home in the Berkshires

House in Sheffield, MA

Hosted by Evolve

Mar 19 – Mar 24

2% savings

Water-View Home in the Berkshires

House in Sheffield, MA

Hosted by Evolve

Mar 19 – Mar 24

Your questions, answered

Nearby Cities

Sandwich, MA, USA Provincetown, MA, USA Harwich, MA, USA Chatham, MA, USA