Experience the Best of Vermont Lodging

Rooms & Cottages In Old Bennington, VT
Elegant room with a cozy fireplace at a top-rated Bennington VT bed and breakfast.

11 Guest Rooms Across Three Historic Buildings

There’s a reason guests keep coming back to Four Chimneys, our beloved Vermont inn. It might be Room 2’s wood-burning fireplace on a snowy night, or the private glassed-in porch off Room 11 in the thick of foliage season, or the Ice House just steps from the main house, cozy and private with its own entrance.

Every room has its own character, and all 11 include a private bath, a full country breakfast each morning, and a full set of amenities. Browse the rooms below to find the right fit, and if you have specific accessibility needs, please review our accessibility page for details.

Check Availability
Filter ::
  • Room Type
  • Bed Type
  • Floor
  • Occupancy
  • Amenities
close
clear filters
Rooms Shown Below
No Rooms Match Your Selections

Main House

Choose a room inside the historic 1916 mansion for the classic Vermont bed and breakfast experience.

Room 1 – Deluxe King

  • King Bed
  • 2 Guests | Second Floor
  • Gas Fireplace
  • Jetted Tub & Walk-in Shower
More Info
Check Rates

Room 2 – Estate King

  • King Bed
  • 2 Guests | Second Floor
  • Wood Fireplace (Seasonal)
  • Two-person Shower
More Info
Check Rates

Room 3 – Deluxe King

  • King Bed
  • 2 Guests | Second Floor
  • Gas Fireplace
  • Jetted Tub/Shower Combo
More Info
Check Rates

Room 4 – Estate Queen

  • Queen Bed
  • 2 Guests | Second Floor
  • Walk-in Closet
  • Tub/Shower Combo
More Info
Check Rates

Room 5 – Estate King

  • King Bed & Twin Bed
  • 3 Guests | Third Floor
  • Gas Fireplace
  • Tub/Shower Combo
More Info
Check Rates

Room 6 – Estate Queen

  • Queen Bed
  • 2 Guests | Third Floor
  • Dormer Windows
  • Jetted Tub/Shower Combo
More Info
Check Rates

Room 7 – Estate Queen

  • Queen Bed
  • 2 Guests | Third Floor
  • Separate Sitting Area
  • Tub/Shower Combo
More Info
Check Rates

Room 10 – Estate King (ADA)

  • Kind Bed & Twin Bed
  • 3 Guests | First Floor
  • Wheelchair Accessible
  • Roll-in Shower
More Info
Check Rates

Room 11 – Deluxe King

  • King Bed
  • 2 Guests | First Floor
  • Private Glassed-in Porch
  • Tub/Shower Combo
More Info
Check Rates
A woman walks barefoot in a garden by an elegant building, perfect for a Vermont Bed and Breakfast experience.
Join Us for Cocktails

Guests are invited to enjoy cocktails each evening from 4 to 9 in the inn’s lounge, where you’ll will find a full bar and wood-burning fireplace.

See More Inn Amenities

Cottages

Set in the estate’s original outbuildings, these rooms offer a cottage-style stay a few steps from the main house.

Room 8 – Deluxe King (Ice House)

  • Kind Bed & Twin with Trundle
  • 4 Guests | Two Levels
  • Private Entrance (Outside Access)
  • Walk-in Shower
More Info
Check Rates

Room 9 – Estate King (Carriage House)

  • King Bed
  • 2 Guests | Ground Floor
  • Private Entrance (Outside Access)
  • Jetted Tub/Shower Combo
More Info
Check Rates

Frequently Asked Questions

Prepare for your Vermont stay with our most common booking FAQs, or see our full FAQ page for more.

Yes. A complimentary full country breakfast is served each morning in the dining room for overnight guests.

Most weekends require a two-night minimum stay. During peak foliage season (September 24 – November 1), a two-night minimum may also apply midweek.

Check-in is from 3:00 pm to 9:00 pm. If you expect to arrive later than 9:00 pm, please contact the inn to arrange a late check-in.
Check-out is 11:00 am.