Simplicity Cottage

5447 Rude Avenue
Tilghman, MD 21671
Popular! Recently viewed by 167 other travelers!

- Renovated watermans cottage circa 1920 - $75 credit for kayak rentals on weekly stays - Dock, firepit, picnic table, benches, grill - Pet-friendly

Pets Welcome







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Renovated Watermans Cottage circa 1920. Wide water views and bay breezes!

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 Baywatching. 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.

Talbot County STR License #ST-108-ALL

Property Information & Notes:

  • Dock Information: Choptank River 40' dock with water, no electricity, 2'


  • Fireplace: Gas fireplace

  • Firepit: Firewood provided.

  • WiFi: Please note that the rural nature of the area limits the data access and some properties can experience slow speeds, or access limited to e-mail and web browsing and not streaming.

  • Pet Policy: This property is dog-friendly for up to two dogs at no additional charge.

  • Grill: This property has a propane grill. Propane is provided.

  • Picnic table and benches

  • Adirondack chairs

  • Swing and hammock

Bed Sizes:

  • Bedroom 1 - Queen

  • Bedroom 2 - 2 Twin

Please Note:

All ESVR properties include bed and bath linens, beds made prior to your arrival, and a starter supply of toilet paper, bathroom soap, paper towels, and dishwater detergent. Please be sure to add these items to your grocery list for the duration of your stay.

Our properties do not allow group rentals to guests under the age of 25. Therefore, online bookings for group rentals will not be honored.

Weddings and special events of any kind are not permitted at our vacation rental properties due to local zoning ordinances and our homeowner agreements.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities shown above. Although they are deemed reliable, they cannot be guaranteed


  • Internet Service = WiFi
  • Microwave = Yes
  • Central A/C = Yes
  • Coffee Maker = Yes
  • Dishwasher = Yes
  • Stove = Yes
  • Location = Waterfront
  • Area = Tilghman Island
  • Unit Type = Single Family
  • Non-Smoking = Yes
  • Pets Allowed = Yes
  • Rental Type = Flex Stay
  • Linens Provided = Yes
  • Oven = Yes
  • Heating = Yes
  • Towels = Yes
  • Dining Area = Yes
  • Smoke Detector = Yes
  • Waterfront = Riverfront
  • Water View = River View

Ask us about Mini Week Availability!

Period Nightly Weekly
01/02/2021 - 04/30/2021 $250 $1500
05/01/2021 - 05/07/2021 $250 $1500
05/08/2021 - 05/14/2021 $250 $1500
05/15/2021 - 05/21/2021 $250 $1500
05/22/2021 - 05/28/2021 $250 $1500
05/29/2021 - 06/04/2021 $250 $1500
06/05/2021 - 06/11/2021 $250 $1500
06/12/2021 - 06/18/2021 $250 $1500
06/19/2021 - 06/25/2021 $250 $1500
06/26/2021 - 07/02/2021 $250 $1500
07/03/2021 - 07/09/2021 $250 $1500
07/10/2021 - 07/16/2021 $250 $1500
07/17/2021 - 07/23/2021 $250 $1500
07/24/2021 - 07/30/2021 $250 $1500
07/31/2021 - 08/06/2021 $250 $1500
08/07/2021 - 08/13/2021 $250 $1500
08/14/2021 - 08/20/2021 $250 $1500
08/21/2021 - 08/27/2021 $250 $1500
08/28/2021 - 09/03/2021 $250 $1500
09/04/2021 - 09/10/2021 $250 $1500
09/11/2021 - 09/17/2021 $250 $1500
09/18/2021 - 09/24/2021 $250 $1500
09/25/2021 - 10/01/2021 $250 $1500
10/02/2021 - 11/12/2021 $250 $1500
11/13/2021 - 11/19/2021 $250 $1500
11/20/2021 - 11/26/2021 $250 $1500
11/27/2021 - 12/24/2021 $250 $1500


This was such a wonderful stay. Home is pristine, quiet and just perfect for our stay. Good wifi but tv channels are limited on rainy days. All kitchen utensils you need to make a huge gourmet dinner. We absolutely loved this stay as it is a relaxing retreat.
Aug 2019
I like the services by ESVR and this is an ideal rental. ESVR reaches out to you when your getaway is close and provides good information. I raised a concern about a glitch from the last trip and I got an appropriate response that assured they were on it. Thanks The place is nicely designed and comfortable. I like the quiet and the nice view of the beautiful Choptank River. It really has everything you would need. It is a great place to stay for a quiet get away. We had an emergency that required us to delay our arrival by two days. We were able to work through it with staff and they could not have been more supportive and helpful. It helped of course that there was vacancy.
Michael Love
Aug 2019
I would recommend Simplicity Cottage. The view on the property is 5 stars. Very relaxing! The cottage was perfect for a couple. We were looking for a water front property to un-wind and relax for vacation. Tilghman Island and Simplicity cottage was the perfect choice. Coffee in the morning overlooking the bay and watching the boats was so serene. We enjoyed watching the OSprey and her babies in her nest on the dock. St. Michaels was a short drive away. Locals were so friendly, restaurants good! The guest service team were great, sending text and emails updating us with information.
Debbie Wolk
Jul 2019
A beautiful spot on the Bay. We stayed with a family of four, and there was plenty of space while still feeling cozy. The view from the backyard is incredible - especially at sunset. Would highly recommend a stay at Simplicity Cottage if you're looking for a peaceful respite!
Jul 2019
The staff was very helpful and friendly. Beautiful location and awesome little cottage. We enjoyed the location and the cottage. If ever we need to stay in the area again, we will definitely stay at Simplicity Cottage if we bring our dog with us. The members of the team were all very helpful. MANAGER RESPONSE: Simplicity Cottage is pet friendly! Up to two dogs are welcome at no additional charge. We hope to see you again soon.
Kit Lisiewski
May 2019
This was our first experience with Eastern Shore Vacation Rentals and we were pleased with how much the property description matched the actual property. Their communications were always timely and very helpful. We LOVED Simplicity Cottage! It was the perfect size for the two of us and our dog -- with room for another couple if we decide to share in the future. We would definitely recommend this to our friends that enjoy relaxing on the water and watching the ducks feed. Simplicity Cottage was the perfect getaway for us and our dog. We only stayed for three days, but wished we had booked for longer. The cottage is in a small neighborhood at the end of a long unpaved lane and situated right on the water. It's small but the perfect size for two people and has another bedroom upstairs for two more. The kitchen was well stocked and the cottage was very clean and tidy. Beautiful sunrises over the Choptank River greeted us every morning. We were there in the off-season so it was a little chilly and there was very little river traffic -- we enjoyed sitting outside in our jackets watching the bufflehead ducks feeding around the dock. Next time we come (and we WILL be booking this house again) we'll bring our kayaks so we can explore more of the river.
Cathy Reynolds
Mar 2019
4.5 Stars!
Nadia Whitt
Jan 2019
Great house with a perfect view that’s close to St. Michaels and Annapolis. Loved it.
Oct 2018
We loved Simplicity Cottage, and we’ve already recommended the spot to a friend who is going to rent it!
Rian Cooney
Jul 2018
Wonderful house and location
Ernesta Ballard
Mar 2018
Excellent experience all around. Easy to book, excellent customer service before our stay as well as during. LOVED It can't wait to return. Excellent experience all around. Easy to book, excellent customer service before our stay as well as during. This was a lovely location, the home was clean and well taken care of, and correctly represented and presented on the website. We got exactly what we booked. I would absolutely recommend it to others. This was a lovely location, the home was clean and well taken care of, and correctly represented and presented on the website. We got exactly what we booked. I would absolutely recommend it to others.
Ann Patten
Jan 2018
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
Aug 2017

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