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

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A white house with a red door and chimney, surrounded by greenery and a view of the water.
A spacious living room with two brown sofas, a wooden coffee table, and a kitchen in the background.
A compact kitchen with a central island, a dining area with a patterned sofa, and a small table with a lamp.
A lakeside property with a house, a grassy lawn, a dock, and a stone wall.
A dining area with a round glass table, four chairs, and a view of the sea through large windows.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Your own private chef
    One of the few properties offering private chef services.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Chesapeake Bay

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue
  • Breakfast for a fee
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Tilghman Island, MD
  • Place, Northern Chesapeake Bay
    ‪19 min walk‬
  • Place, Tilghman Watermen’s Museum
    ‪4 min drive‬
  • Place, St. Michaels Winery
    ‪29 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪49 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

1 bathroom, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub · Toilet · Shower only · Hair dryer

Bathroom 2

Soap · Toilet · Hair dryer

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden
Dining area

Add dates for prices

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  • Washing machine
  • Dryer
  • Air-conditioning
10.0 out of 10, Exceptional, (14 reviews)
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About the area

Tilghman

Located in Tilghman, this cottage is on the waterfront. The area's natural beauty can be seen at Chesapeake Bay and Northern Chesapeake Bay, while Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum are cultural highlights. Phillips Wharf Environmental Center and Chesapeake Beach Railway Museum are also worth visiting.
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Map
Tilghman Island, MD

What's nearby

  • Northern Chesapeake Bay - 19 min walk - 1.6 km
  • Tilghman Watermen’s Museum - 4 min drive - 3.1 km
  • Chesapeake Bay Maritime Museum - 28 min drive - 32.1 km
  • St. Michaels Winery - 29 min drive - 32.8 km
  • Saint Michaels Village - 30 min drive - 34.2 km

Getting around

  • Cambridge Station - 64 min drive
  • Easton, MD (ESN-Easton - Newnam) - 39 min drive

Restaurants

  • ‪Big Mack's Kitchen & Dock Bar - ‬4 min drive
  • ‪Gina’s @ The Bridge - ‬4 min drive
  • ‪Tickler's Crab Shack and Restaurant - ‬3 min drive
  • ‪Two if by Sea - ‬3 min drive
  • ‪Marker Five Waterfront Dining - ‬4 min drive

Frequently asked questions

Is Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE?

On-site parking is available at the property.

What time is check-in at Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE?

Check-in begins at 3:00 PM.

What time is check-out at Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE?

Checkout is at 11:00 AM.

Where is Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE located?

Situated on the waterfront, this cottage is within 1 mile (2 km) of Chesapeake Bay, Northern Chesapeake Bay and Tilghman Watermen’s Museum. Talbot County Library Tilghman Branch and Kronsberg Park are also within 2 miles (3 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 24 out of 27 reviews
Rating 8 - Good. 2 out of 27 reviews
Rating 6 - Okay. 1 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful setting and home. Will recommend to friends and family. We always enjoy the area and history. Locals are all so friendly and accommodating.
Stayed 3 nights in Sep 2026
Response from VrboOwner on 3 October 2026
Thank you for your review. We ae happy you enjoy our cottage and Tilghman Island. and look forward to our return.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely cottage with great Bay views. Cozy, clean, quiet - perfect dog-friendly getaway!
Stayed 3 nights in Aug 2026
Response from VrboOwner on 21 September 2026
Our views are the best - we are happy you and your pet enjoyed our wonderful Simplicity Cottage
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice place to go relax love the house caught crabs right off the dock would recommend this place to anyone who wants peace and quite
Stayed 4 nights in Aug 2026
Response from VrboOwner on 21 September 2026
We are pleased that you feel the same about our wonderful Simplicity Cottage
Verified review

8/10 Good

Liked: Cleanliness, check-in, location, listing accuracy
Excellent location on beautiful Tilghman Island. Well equipped kitchen and plenty of outdoor furniture to enjoy the views and sit on the dock.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I absolutely fell in love with this cottage. I walked a lot, spent time painting and slow stitching, and made a few fun trips into St. Michael's. I will be back next year definitely and perhaps this winter. If it's ever on the market I would scoop it up in a minute!! Thank you Barbara and Karen!
Stayed 5 nights in Sep 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
This cottage is a very nicely renovated, it feels large and cozy at the same time. The kitchen was well equipped and easy to use, The bed was comfortable as were the sofas and a nice selection of outside chairs. The gas grill was good. The views of the bay are great and other houses were not in sightlines to bay. We were there during the 100 4th of July heat, so we were inside a lot, the AC was cool. Near by VG restaurant Two If By Sea!
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great little cottage, just as described!We were in town for a wedding and loved waking up to the sunrise over the water (and sunsets!)When we first entered, I noticed a musty smell, but it went away soon after we turned on the air-conditioning and I lit a couple candles that I brought. We were there during a record heat weekend and the air conditioner worked well.Loved that it was pet friendly, our Boykin Spaniel had a blast.Super easy check-in and check-out. Host was great!Many thanks for sharing this precious cottage with us!
Stayed 3 nights in Aug 2026
Response from VrboOwner on 29 August 2026
We are happy you enjoyed your stay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in May 2026
Response from VrboOwner on 25 May 2026
Exactly what we love about our wonderful property,
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stunning property! Stunning bay front with a cool dock. Quiet! Everything we needed. Perfect spot to totally unplug from DC Metro madness!! Obviously, we had the best crab cakes in the world. We are Marylanders! We KNOW If you are looking to totally unplug(yes, there’s good AC and WiFi) This is the place. A million likes
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything about the place was perfect for a getaway loved the place everything was handy and setup perfectly to relax and enjoy the scenery
Stayed 3 nights in Aug 2025
Response from VrboOwner on 14 October 2025
Thank you for appreciating our perfect getaway.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our most relaxing vacation yet! This cottage was perfect for our trip. Clean, spacious and the views were worth the trip. The bed was comfortable and we appreciated that. The kitchen was well equipped and the grill was perfect for the two of us. The cottage had everything we needed. There isn’t a hammock as shown in the photos but there are 2 Adirondack chairs we spent quite a bit of time in watching the boats go by. The area is quiet and peaceful. We saw heron, osprey and an egret, as well as several crabs right at the dock. The WiFi worked well as I worked one day while there.
Stayed 4 nights in Jul 2026
Response from VrboOwner on 29 August 2026
We are happy you enjoyed your stay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
nice place . large kitchen which was helpful because we made a large meal.
Stayed 3 nights in Sep 2025
Response from VrboOwner on 18 May 2026
We are lad you enjoyed our open floor plan as well as the broad view of the water.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Aug 2025
Response from VrboOwner on 14 October 2025
We appreciate your enjoying our wonderful cottage on the bay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Aug 2025
Response from VrboOwner on 14 October 2025
Thank you for appreciating our wonderful cottage o the bay.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tranquil Getaway

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!
Stayed 3 nights in Jul 2025
Response from VrboOwner on 30 July 2025
Thank for your wonderful review. We know that Simplicity Cottage" offers the best quiet views for guests and their fury friend. Please come again. Barbara
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved it.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 18 May 2026
Glad you enjoyed our Simplicity Cottage.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing!

Quiet, peaceful, relaxing!
Stayed 5 nights in Sep 2024
Response from VrboOwner on 8 October 2024
So glad your stay was exactly what you wanted.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dreamy!

Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing spot!

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.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tilghman Island Cottage

If you want to get away from it all, this is the place to be. My wife and I celebrated our 20th wedding Anniversary. Calm and peaceful, nestled right by the Choptank River. The cottage itself was very comfortable. The air conditioner worked great. It was a pleasure staying there and we will probably return next year.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 8 October 2024
So happy your stay was what you expected and maybe more. Look forward to your return visit again soon.
Verified review

6/10 Okay

Liked: Cleanliness, check-in, location, listing accuracy
Lovely location. The dock was great for crabbing. Stunning views of the bay. I was very disappointed at the grass being very overgrown. We had planned outdoor activities, but struggled to play since the grass was so tall. When I reached out to the owner/property manager, I received a sarcastic response, however the landscaper was called. We finally had the lawn mowed at 3pm the day before we had to check out. Once the lawn was mowed, it was gorgeous. It should have been taken care of before our arrival. We also had to walk through the tall grass to get to the dock and car. In addition, for a party of 4, you receive 4 shower towels with no additional back-up. There were extra blankets, but when I asked about towels, I was told that this is what they supply. The kitchen supplies such as pans and coffee maker were old. The dock and view were by far the best part. The crabbing was great.
Stayed 3 nights in Aug 2026
Response from VrboOwner on 29 August 2026
We apologize . We never intend to be sarcastic As you know, Rain and the lawn service schedule prevented the lawn from being cut a second time in one week. Your wife told me she found the additional towels on the second floor and never mentioned
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Jul 2025
Response from VrboOwner on 30 July 2025
Your review describes "Simplicity Cottage" the best! We are delighted your had a wonderful experience and we hope yo will return soon. Thank you Barbara
Verified review

10/10 Excellent

Liked: Location
A lovely cottage on the water. There was lots of room and the AC cranked. We enjoyed the peace and quiet. Thanks for having us.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 3 nights in May 2026
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