Pet-Friendly Tilghman Island Coastal Retreat

Tilghman Island, Maryland
$427 avg/night
Minimum Stay 3 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 5

Max Sleeps

Night 3 nights

Min Stay

Summary:
Escape to this beautifully designed Tilghman Island retreat, the perfect blend of coastal charm and modern comfort. Ideal for families, couples, and small groups, this pet-friendly getaway offers everything you need for a relaxing Chesapeake Bay vacation — just minutes from St. Michaels and the island’s best waterfront dining.

Talbot County Licensure: STRN-24-72

The Space:
Step inside to a bright, open-concept living area filled with natural light. Thespacious living room features an oversized sectional, cozy fireplace, and large windows that bring the outdoors in. The fully equipped kitchen has everything you need to cook family meals or host a casual get-together after a day of exploring. The comfortable bedrooms ensure restful nights with plush bedding and thoughtful touches throughout. High-speed Wi-Fi and smart TVs make it easy to relax and stay connected.

Spend your days soaking in the relaxed island pace. The private backyard is perfect for yard games, morning coffee, or evening cocktails under the stars. Enjoy dining al fresco on the patio or gather around the fire pit to share stories and make s’mores.

Why Guests Love It:
- Pet-friendly – bring your furry family members!
- Quiet island setting – peaceful, private, and just minutes to restaurants and marinas.
- Perfect for all seasons – sunny summer escapes, cozy winter weekends, and everything in between.
- Family-friendly amenities – spacious layout, full kitchen, outdoor space for kids and pets.

Explore nearby St. Michaels, enjoy fishing charters, visit the Chesapeake Bay Maritime Museum, or take a scenic bike ride around the island. Tilghman offers a rare mix of small-town charm, waterfront views, and easy access to all that Maryland’s Eastern Shore has to offer.

Curated by Flaneur, this experience is designed in the spirit of slow travel , where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.

Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

The Neighborhood:
Tilghman Island is a picturesque Eastern Shore gem, known for its working watermen’s culture, fresh seafood, and scenic beauty. Within minutes, you can enjoy waterfront dining, boutique shopping, and maritime history in St. Michaels — just a short drive away.

Other Things to Note:
Starter supply of paper towels, toilet paper, and basic toiletries provided.

Please bring extra supplies if you prefer more than the starter set.

Pets welcome upon approval — $200 non-refundable fee.

Quiet, residential neighborhood — respect local noise guidelines.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • 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

    3 Bedrooms Bed Sheets Provided
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    WiFi Available
  • OUTDOORS

    Balcony Firepit Garden
  • BATHROOMS

    2 Bathrooms Hair Dryer Shower Towels Provided
  • WORKSPACES

    Desk Office
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Golf Privileges
  • ENTERTAINMENT

    TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Toys
  • LOCATION HIGHLIGHTS

    In A Rural Location
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 5

Map Map

School District Availability

Review Review

  • Ryan M.

    Submitted May 17, 2026

    Stayed May 14, 2026

    Close as you can get to the black walnut. Great spot for a small group or family in town.

  • Ashley T.

    Submitted Apr 7, 2026

    Stayed Apr 2, 2026

    We really enjoyed our time here and would recommend to others!

  • MELISSA M.

    Submitted Oct 22, 2025

    Stayed Oct 16, 2025

    Very nice home. Only issue was one kitchen window that didn’t latch therefore upper sash would not stay up and was letting in some bees but we were able to take care of it. The layout of the 1st floor bathroom is a bit odd and the couple steps that could be hazardous if you’re not paying attention. Wonderful location right up the street from the public pier in a nice quiet neighborhood. Property manager responded quickly to my messages.

  • Mary C.

    Submitted Sep 3, 2025

    Stayed Aug 29, 2025

    The house was wonderful for our small group. We loved being able to walk to the public dock and bike to Tickler's and Gina's for meals. The bedrooms were clean and cozy and we had great movie nights in the den downstairs. The firepit was also a huge hit. We will definitely return!!

  • BRANDON W.

    Submitted Jun 21, 2025

    Stayed Jun 8, 2025

    Tastefully restored traditional property in a quiet location. Plenty of equipment, though an electric kettle would improve this further. Lots of space!

  • Robert J.

    Submitted Sep 24, 2024

    Stayed Sep 14, 2024

    If you are looking for a quiet, serene, comfortable setting for your upcoming visit to Tilghman Island, I’d highly recommend the Skipjack Cottage. While the exterior of the cottage is a tad weathered, the interior was lovely with a great combination of restoration and contemporary appointments. All three bedrooms were nicely decorated, clean and comfortable. The modern kitchen has all that’s needed for meal preparation and dining. We would go back in a heartbeat!

  • Alexandra J.

    Submitted Jul 30, 2024

    Stayed Jul 19, 2024

    We had a wonderful stay here. It is so charming, beautiful inside, very clean and fit perfectly with the vibe of the island. Loved being able to walk to the pier to go crabbing. You will love this place. Highly highly recommend!

  • Daniel M.

    Submitted Jul 17, 2024

    Stayed Jul 13, 2024

    The skipjack cottage was amazing. Our group of friends have been exploring different regions of the Eastern Shore for about two decades and we'll definitely be back to Tilghman Island. We appreciated that the house had a full kitchen (complete with utensils, implements, and staples) and tasteful finishes and furnishings throughout the house. The neighborhood was calm and quiet, the public dock was a short walk away for fishing and relaxing near the water, and the low speed roads on Tilghman Island were perfect for biking. Thanks for offering this property

  • Libby D.

    Submitted Jul 2, 2024

    Stayed Jun 20, 2024

    The house was very cute, kept old style southern charm with many modern updates. Great space for a family trip. The beds were very comfortable. Minor plumbing issues towards the end of our trip. We unfortunately picked a very hot week to visit so there was not much to do nearby, (closest public beach an hour away) but thankfully the house was well air conditioned. The neighborhood was quiet, beautiful, well kept, neighbors were very friendly. We enjoyed waking down to the dock several times a day and sitting on the porch people watching.

  • C. Jason B.

    Submitted Jun 14, 2024

    Stayed Jun 7, 2024

    A delightful, quiet and peaceful spot for a family getaway.

Your dates are Available!

Total

Includes taxes and fees
$427+
View details