We love the Brampton Inn

Chesapeake Beach Resort
St. Michael's Harbor Inn
Inn at Herrington Harbor

Check out B&Bs near St. Michael's or Rock Hall, MD. Also note that some places with a Chestertown, MD address are not in the town area, but in the surrounding countryside. For example, Great Oak Manor is lovely. Inn at Osprey Point is also nice - but a little more activity there since they have a marina. For that one, get a room on the 3rd floor for a little more quiet. They have bikes to borrow and you can see if there's any good bands at the Mainstay.

http://www.stmichaelsmd.org/list/category/bed-breakfast-inns-120
https://www.kentcounty.com/lodging-type/inns

We really enjoyed our stay here:

http://www.victorianainn.com/

Cambridge Hyatt

Anonymous wrote:Inn at Perry Cabin

Looks lovely, but we'd rather pay a bit less, say $300 or less.

Any suggestions?

Inn at Perry Cabin

DH and I have a one-night window to get away without kids.

I desperately want to stay someplace where I can spend time just gazing at the water, maybe over a glass of white wine in an Adirondack chair or similar. Kayaking would be a bonus. If there is a little beach nearby, all the better.

Any suggestions?

Thank you!