Simplicity Cottage

Tilghman, MD

Beds 2

Baths 1.5

Guests 4


View Floor Plan

Renovated Waterman's Cottage circa 1920. Wide water views and bay breezes!

Talbot County STR License ST-108-ALL

This fantastic 1920's Waterman's cottage has the charm and waterfront location that is hard to come by these days. Restored to give you some up-to-date comforts such as a new kitchen, an additional bedroom and a renovated bath, this is a great spot to enjoy hours of bay watching. You can also easily slip over to Dogwood Harbor and observe one of the last skipjack fleets in the country.

Pick up some fresh seafood and savor a local meal at home with the best seat in the house - all this while watching the osprey and eagles soar across the open sky. This is a great cottage for those who still appreciate the simple things in life.

What's Nearby?

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A. Cancellation by Agent: Agent may cancel this Agreement at any time, prior to Renter taking occupancy, and refund Renter all money paid. The Property must be occupied by the Renter identified above and all occupants of the premises shall be supervised by that Renter . Violation of this provision is grounds for immediate removal and Renter will forfeit all monies received by Agent . Agent also may cancel this Agreement without refund to Renter if Renter or Renter’s family or other invitees intentionally damage the Property, fail to comply with any provision of this Agreement or any applicable law, violate the rules and regulations of any applicable homeowners or condominium association, disturb the peace, become verbally abusive and/or threaten any Agent employee or contractor, or otherwise act in a manner inconsistent with the good character of the Property and the surrounding neighborhood. In the event the Property becomes uninhabitable subsequent to execution of this Agreement but prior to Renter’s Arrival Date, Agent reserves the right to relocate Renter to comparable alternative accommodations in the same geographic area as the Property, in which case no cancellation will occur.

B. Cancellation by Renter: In the event a Renter requests a cancellation of this Agreement, Agent will return the Property to the rental market and use the same efforts to re-rent the Property as Agent uses for other properties. Under such circumstances:

i.     if Agent is able to re-rent this Property for the same dates of stay for the same amount or greater, Renter will be entitled to a refund of all amounts paid under this Agreement, less Agent's prevailing Processing Fee and Credit Card Processing Fee as referenced on receipt for this transaction;

ii.    if Agent is able to re-rent this Property for the same dates of stay, but only for a lesser amount, Renter will be entitled to a refund of all amounts paid under this Agreement, less the Processing Fee and Credit Card Processing Fee, and less the difference between the amount of the original booking and the amount for which Agent was able to re-rent the Property; and

iii.   if Renter requests a cancellation of this Agreement thirty (30) days or more in advance of the Arrival Date, and Agent is unable to re-rent this Property for the same dates of stay, Renter will forfeit one-third (1/3) of full rental amount called for under this Agreement, plus the Processing Fee and Credit Card Processing Fee. If, however, Renter requests a cancellation of this Agreement less than thirty (30) days in advance of the scheduled Arrival Date, and Agent is unable to re-rent this Property for the same dates of stay, Renter will forfeit the full rental amount called for under this Agreement.

All cancellations by Guest must occur prior to the beginning date of their stay, or no refunds will be provided. Nor will a refund be given if Guest refuses to take occupancy of the Property. As such, ESVR strongly recommends that Guest view images of the Property prior to booking their reservation. Rental units managed by ESVR are privately owned and reflect the personal needs and tastes of the individual Owners. For this reason, the furnishings and decor will vary according to each owner’s desires, and no refunds will be given based on complaints concerning the Property’s furnishings or decor. ESVR will endeavor to address any equipment malfunction promptly on behalf of Owner (such as televisions, VCRs, microwaves, etc.), but no refunds will be given as a result of the malfunction of such equipment – even if a repair or replacement is not available. No refunds will be given for inclement weather (including hurricanes or other acts of nature) or any other matter which may inconvenience Guest’s stay at the Property but which is beyond the control of ESVR or of Owner. For this reason, ESVR strongly suggests that Guest purchase the Travel Protection offered.  In addition, no refunds will be provided for any actual or alleged inconvenience experienced by Guest as a result of any inconvenience resulting from construction or special events, or in the event, the Property’s pool is not open during Guest’s stay.



Lovely house, lovely view, love peace and quiet.
Rod M.
Stayed on 2022-11-28

Serene & Peaceful

If you want a serene & peaceful place to relax, this is your location. ...Read More
Anulekha M.
Stayed on 2022-07-04


Great Cottage! Lovely cottage overlooking the bay.
James R.
Stayed on 2022-06-11


The cottage is lovingly maintained with great views. We had everything...Read More
Kate W.
Stayed on 2022-06-05

Simplicity Cottage

Loved this property, location is so beautiful and quiet......We had a wonderful time !!!
Elizabeth N.
Stayed on 2021-07-31

Simplicity Rules!

We enjoyed Simplicity Cottage immensely. We were there most of 2 weeks ...Read More
Mike W.
Stayed on 2021-07-19


I like the services by ESVR and this is an ideal rental. ESVR reaches o...Read More
Michael Love
Stayed on 2019-08-17


This was such a wonderful stay. Home is pristine, quiet and just perfec...Read More
Stayed on 2019-08-04


A beautiful spot on the Bay. We stayed with a family of four, and there...Read More
Stayed on 2019-07-18


I would recommend Simplicity Cottage. The view on the property is 5 sta...Read More
Debbie Wolk
Stayed on 2019-07-14


The staff was very helpful and friendly.Beautiful location and awes...Read More
Kit Lisiewski
Stayed on 2019-05-07


This was our first experience with Eastern Shore Vacation Rentals and w...Read More
Cathy Reynolds
Stayed on 2019-03-31


4.5 Stars!
Nadia Whitt
Stayed on 2019-01-22


Great house with a perfect view that’s close to St. Michaels and Annapolis. Loved it.
Stayed on 2018-10-07


We loved Simplicity Cottage, and we’ve already recommended the spot to a friend who is going to rent it!
Rian Cooney
Stayed on 2018-07-23


Wonderful house and location
Ernesta Ballard
Stayed on 2018-03-22


Excellent experience all around. Easy to book, excellent customer servi...Read More
Ann Patten
Stayed on 2018-01-21


Quaint, secluded, cozy and serene. Exactly what we were looking for and a lovely little cottage to boot. A perfect place for a getaway to decompress
Stayed on 2017-08-05