Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island, Maryland
$533 avg/night
Minimum Stay 3 Nights
Bed 2

Bed

Bath 1

Bath

Home Cottage

Property Type

Sleep 4

Max Sleeps

Night 3 nights

Min Stay

STRN-23-58
Simplicity Cottage is a circa 1920 Waterman's Cottage. 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. Windows that captivate the natural beauty of the area. New kitchen, and 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 ofthe 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. Fireplace adds to the charm.

Property Information & Notes:
Dock is available for guest use- fishing, crabbing, photography, reading, relaxing and just gazing
There are charters available as well on the island.
Hunting groups nearby offsite & in season
Cyclists and athletes are welcome.
Freedom for creative, contemplative, joyful time
Trailers allowed only as part of the 2-car max: No parking in the lane or grass.
Small crafts NON-MOTORIZED allowed, no jet skis.
No water toys included: HOMEOWNER PROVIDES $75 CREDIT TOWARD KAYAK OR BICYCLE RENTALS FOR WEEKLY RESERVATIONS
Fireplace: Gas fireplace
Wifi: High speed
Pet Policy: This property is dog-friendly for up to two dogs for $100 per pet with pet addendum.
Grill: This property has a propane grill. Propane is provided.
Picnic table
benches- do not leave on the end of the dock. Especially in bad weather
Adirondack chairs
Swing and Hammock
Bed size:
Bedroom 1- Queen
Bedroom 2- Two Twins

Please Note:
This property includes 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 property does not allow group rentals to guests under the age of 25. Therefore, online bookings for group rentals will not be honored.
Wedding and special events of any kind are not permitted at our vacation rental property due to Talbot County Short Term Rental License ordinances.

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.

This 2-bedroom house provides accommodation with Kitchen, Laundry, Bedding/Linens, for your convenience. This house features many amenities for guests who want to stay for a few days, a week or a longer vacation with family and friends. This house is located on Tilghman Island and gives visitors the opportunity to explore it. It has 2 bedrooms and 1.5 bathrooms to make you feel right at home.

Check to see if this house has the amenities, you need and a location that makes this a great choice for you to stay in Tilghman. Call our office for more information. Chesapeake Bay Real Estate Plus - Barbara Focht (610-220-5212) cell

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    1 Total (up To 50 Lbs Per Pet) Pet Friendly Service Animals Exempt From Fees Welcoming Dogs Only
  • DINING

    Breakfast Available For A Fee Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee Grinder Dishwasher Electric Kettle Ice Maker Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Wheelchair-accessible Parking Available
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Garden Outdoor Furniture Patio
  • BATHROOMS

    1.5 Bathrooms Hair Dryer Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Kayak On Site
  • ENTERTAINMENT

    Books DVD Player Games Music Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Playground
  • LOCATION HIGHLIGHTS

    On The Waterfront
  • SERVICES AND CONVENIENCES

    Chef Concierge Services Housekeeping (on Request) Phone
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces 3 Stairs To Reach Property Area Rugs In Public Areas Handrails In Stairways If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Smooth Flooring In Public Areas Wheelchair Accessible Wheelchair-accessible Parking

CheckIn Check-in : 03:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Availability

Review Review

  • Nelson B.

    Submitted May 18, 2026

    Stayed May 14, 2026

    Great property and location on the water. Prepare for beautiful sunrises, birds galore, and nesting Ospreys right outside. Close to everything on Tilghman and St. Michaels Islands. You will not be disappointed.

  • John S.

    Submitted Oct 14, 2025

    Stayed Sep 26, 2025

    nice place . large kitchen which was helpful because we made a large meal.

  • Suzanne W.

    Submitted Oct 13, 2025

    Stayed Oct 3, 2025

    Loved it.

  • Diann C.

    Submitted Aug 22, 2025

    Stayed Aug 8, 2025

    Our stay at Simplicity Cottage was absolutely perfect. The cottage is well appointed with everything we needed and we fell asleep to the lapping water just steps from our door.

  • David M.

    Submitted Aug 19, 2025

    Stayed Aug 15, 2025

    Everything about the place was perfect for a getaway loved the place everything was handy and setup perfectly to relax and enjoy the scenery

  • Douglas S.

    Submitted Aug 15, 2025

    Stayed Aug 11, 2025

    This is a great place to relax, unwind, and enjoy the Chesapeake on an island totally removed from the hustle and bustle of the city. The Bay views can’t be beat.

  • Lori E.

    Submitted Jul 14, 2025

    Stayed Jul 7, 2025

    This is a slice of heaven! Great views, sunrises, fishing, crabbing, clean and the the best appointed kitchen ive ever had the pleasure to rent. Tons of fluffy towels! The rental agent was super responsive for every need. There's an eatery, country store, charters and fabulous boho woman's store on the island. Tons of shopping in famous St. Michaels a short drive away. Go to Easton for groceries, amish market and pretty much every store you need. This is your peaceful retreat you have dreamed of.

  • Katie M.

    Submitted Jul 6, 2025

    Stayed Jul 3, 2025

    Absolutely adorable cottage with a great yard to relax and enjoy the view. Fully stocked kitchen and had everything we could need. Tilghman island is adorable and the cottage is a quick drive to lovely St Michael’s. Really enjoyed our stay and would recommend, especially if you want to bring your dog!

  • John M.

    Submitted Jun 14, 2025

    Stayed Jun 6, 2025

    Peaceful with beautiful water views. House is in good shape, and only a couple houses nearby. Saw plenty of osprey, turkeys near the woods and skates prowling the waters at night.

  • Torrey P.

    Submitted May 18, 2025

    Stayed May 2, 2025

    A few local spots to eat were great in the morning especially the Tighlman Market! Market has all you need to stock up with groceries and is just 2 minutes from the house.

  • Submitted Mar 8, 2025

    Stayed Nov 28, 2024

    Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again

  • Sheldon J.

    Submitted Sep 24, 2024

    Stayed Sep 18, 2024

    Quiet, peaceful, relaxing!

Your dates are Available!

Total

Includes taxes and fees
$536+
View details