A Victorian guest house in the heart of Chestertown

Chestertown Bed and Breakfast
402 High Street | Chestertown, MD 21620 | Ph: 410-778-6455 |1-888-778-6455 | widwalk@gmail.com

The Inn  |  Accommodations   |  Rates  |   Directions

The Widows Walk Inn B&B is located in the Historic District of Chestertown, on Maryland's Upper Eastern Shore, only 1 1/2 hours from Washington, Baltimore and Philadelphia.  Situated on High Street, the Inn is within a short walking distance of the Chester River, Washington College, many homes and buildings of historic significance, as well as quaint gift shops and fine restaurants.

There are many area activities including Boating, Hunting, Golfing, Fishing, Biking, Birding, Antique and Boutique Shopping.  Award winning restaurants as well as casual eateries can be found in Chestertown and throughout the County.  Click on the links below for detailed information.

Historic Chestertown | Recreation | Dining | Shopping |Attractions

"We extend a gracious invitation to join us in our lovely home that we hope provides an oasis that soothes the spirit and allows you to know how things used to be.....and still are in Chestertown."

Bob & Susan Lathroum, Innkeepers

The Inn   top

At the Inn, you will find comfortable lodging with the atmosphere and warmth of a family home.  The Inn is furnished with an eclectic collection of antiques and family treasures.  While our parlor is equipped with cable TV, table books and games, and offers a cozy retreat for conversation, the Inn also has four porches, including a screened rear porch and the large front porch complete with rocking chairs and a swing.  You are also invited to sit and relax on an attractive patio surrounded by gardens; the perfect place to discover a great book.

  • All guest rooms are air conditioned and have ceiling fans.
  • Off-street parking is available at the Inn.
  • We do not accept pets at the Inn.
  • We welcome children over 12.
  • Smoking is permitted on the porches only.
  • A full breakfast is served each morning in the Dining Room that includes fresh fruit, a selection of juices, and of course, coffee and tea.
Chestertown accomodations Chestertown accomodations
Chestertown accomodations

Accommodations  top

Chestertown B&B

The Maryland Suite - The only bedroom on the first floor, the Maryland Room has a queen size bed, a sitting area and an attached private bath.

Chestertown B&B

The Chesapeake Suite - The original master bedroom of the house, the Chesapeake Room
also has a queen size bed, a sitting area,
and an attached private bath.

Chestertown lodging

Sassafras Room
- On the 2nd floor, the Sassafras Room features a king size bed and a private hall bath which contains a large claw-foot tub.

Chestertown lodging

Corsica Room -The Corsica Room has a king size bed (which can be converted into two twins) and shares a semi-private hall bath.

Chestertown lodging

The Bohemia Room - The Bohemia is furnished with a queen size bed and shares the semi-private hall bath.

Rates  top
Check Availability On Line

Weekends -

Weekend rates range from $130.00 to $170.00

Weekdays -

Weekday rates range from $110.00 to $130.00

Room rates are subject to Maryland Tax.  Please note that we observe a 10 day cancellation policy, and for weekend stays, a two (2) night minimum is requested.

Visa and MasterCard are accepted to confirm your reservation; however, we respectfully request that payment for your stay with us be made either by check or cash.

Check In:    Between 3 P.M. and 9 P.M. (late check-in available with advance notice.)
Check Out: 11 A.M.

Directions top

From Baltimore, Washington, Virginia:

* Take I 97 South, or Rt 50 East, to Annapolis
* In Annapolis, take Rt 50/301 East, across the    Chesapeake Bay Bridge
* After crossing the bridge, proceed approx. 10    miles to the point where Rts. 50 and 301 split.    Follow Rt 301 (bear left) the overhead sign says    Wilmington.
* Continue on Rt 301 for approx. 6 miles to MD Rt    213 North. The overhead sign says Centreville.
* Take Rt 213 through Centreville to Chestertown    (18 miles)

In Chestertown:
* Cross river, go to 2nd stoplight, Spring Avenue,    turn left
* Go to first stoplight, High Street, turn right
* Proceed 1 1/2 blocks.  Inn is large Victorian across    from church. Drivieway on right side of Inn.

From New York, New Jersey, Philadelphia:

* Take I 95 South, through Wilmington, DE to Exit     1-A -Rt 896 S to  Middletown,DE
* Take 896 South, following the signs directing you    towards Rt 301.(whenever possible, stay in the    right lane, as you will be bearing right at two road    junctures).
* Follow Rt 301 South to the exit for Rt 290 -    Chestertown-Galena.  At the bottom of the ramp,    turn right.
* At the first stoplight, in Galena, go straight on Rt    213.  Take Rt 213 to Chestertown.

In Chestertown:
* Bear right on Spring Ave. (5th stoplight in    Chestertown)
* Go to first stoplight, High Street, and turn right
* Proceed 1 1/2 blocks.  Inn is large Victorian across    from church.  Driveway on right side of Inn.

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