Entire home

Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!

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A wooden pier extending into calm waters with a distant island, a bench, and a small structure on the right. - Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! (Tilghman)
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A room with a large window, wicker furniture, and a white lamp. - Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! (Tilghman)
A rectangular swimming pool with a tiled deck, surrounded by white lounge chairs and a covered patio area. - Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! (Tilghman)
Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! provides amenities, such as a garden and laundry facilities. Stay connected with in-room WiFi.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms4 bathrooms

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Add dates for prices

About this property

Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!

  • Summary:

    Experience the ultimate Chesapeake Bay getaway on Tilghman Island! This stunning waterfront retreat will feature a brand new pool ready for Summer 2026, perfect for relaxing, soaking up the sun, and enjoying breathtaking bay views.



    Talbot County Licensure: ST-557-LEE



    The Space:

    Experience the beauty of Tilghman Island in this open-concept waterfront home, perfectly positioned on the Chesapeake Bay. Enjoy a private dock for fishing, crabbing, or launching kayaks, and soak in unforgettable sunset views from the deck.

    Inside, large bay-facing windows fill the home with light. The living room is perfect for gathering, while the fully equipped kitchen makes cooking for a group a breeze. With three bedrooms (all with water views) and two full baths, this property comfortably accommodates up to 8 guests.



    What you'll love:

    - Private waterfront dock

    - 2 kayaks with paddles

    - Furnished deck & outdoor dining area

    - Gas grill

    - Fully equipped kitchen with modern appliances

    - High-speed WiFi & streaming TV



    Location Highlights:

    - Quiet setting with bay breezes

    - Short drive to St. Michaels



    This property blends peaceful waterfront living with easy access to the best of the Chesapeake.



    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 waterfront 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.



    Getting Around:

    Bike, Walk , Drive



    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.



    Quiet, residential neighborhood — respect local noise guidelines.



    The private pool is scheduled to open for the season by Memorial Day.

Property amenities

Pool/Spa

  • Communal pool
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Bathtub
  • Hair dryer
  • Shampoo
  • Shower
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Games
  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • On the waterfront

Things to do

  • Cycling nearby
  • Fishing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden

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Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.

About the area

Located in Tilghman, this holiday home is in a rural area and on the waterfront. Tilghman Watermen’s Museum and Chesapeake Bay Maritime Museum are cultural highlights, and some of the area's activities can be experienced at Knapp's Narrows Marina & Inn and Tilghman Island Marina. Phillips Wharf Environmental Center and Chesapeake Beach Railway Museum are also worth visiting. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby. Visit our Tilghman travel guide
View more Holiday homes in Tilghman
Map
Tilghman, MD

What's nearby

  • Tilghman Watermen’s Museum
    14 min walk - 0.8 miles
  • Talbot County Library Tilghman Branch
    19 min walk - 1.0 mile
  • Kronsberg Park
    3 min drive - 1.8 miles
  • Knapp's Narrows Marina & Inn
    3 min drive - 2.2 miles
  • Phillips Wharf Environmental Center
    4 min drive - 2.4 miles

Getting around

  • Easton, MD (ESN-Easton - Newnam)
    43 min drive

Restaurants

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

Frequently asked questions

Does Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! have a pool?

Yes, this property has a pool.

Is Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!?

On-site parking is available at the property.

What time is check-in at Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!?

Check-in begins at 4:00 PM.

What time is check-out at Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!?

Checkout is at 10:00 AM.

Where is Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! located?

Situated on the waterfront, this holiday home is steps away from Chesapeake Bay and Northern Chesapeake Bay. Tilghman Watermen’s Museum and Talbot County Library Tilghman Branch are also within 1 mile (2 km).

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Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026! Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 28 out of 30 reviews
Rating 8 - Good. 2 out of 30 reviews
Rating 6 - Okay. 0 out of 30 reviews
Rating 4 - Poor. 0 out of 30 reviews
Rating 2 - Terrible. 0 out of 30 reviews

10

Cleanliness

10

Location

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This property was so BEYOND anything we could have imagined! We were in town for a wedding and there was plenty of room for our family. The house was immaculate and all of the appliances were top quality. The beds were incredibly comfortable too. BUT - the best thing (other that the view and waterfront location) was the GORGEOUS swimming pool with a retractable cover. We all decided we can't wait to return - and for longer next time!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

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

Paradise at Tilghman Island

Four of us gathered for out annual reunion in this beautiful house. It was comfortable, clean and very well appointed.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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

Great long weekend

Five of us enjoyed this house and location. Great place to recharge and relax. Thinking of returning next year.
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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

Perfect Get Away

Beautiful location. Lots of Osprey, fishing and good weather . House was perfect as well. Everything neat and tidy.
Stayed 7 nights in Apr 2025
Verified review

8/10 Good

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

Nice getaway!

We had a wonderful time. There was plenty of space in the house, beautiful views, and the sunsets were amazing! It was also nice being close to St. Michaels for shopping, restaurants, etc. We really enjoyed our stay.
Stayed 3 nights in Dec 2024
Verified review

10/10 Excellent

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

Great stay!

House very well-appointed with beautiful views. Appreciated all of the amenities available - we utilized the beach chairs, hammock, and swim ladder off the dock. Cooked every night and were lacking nothing in the kitchen. Great stay!
Stayed 4 nights in May 2024
Verified review

10/10 Excellent

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

great property in a scenic location

Highly recommend this property. the views were astounding and made the evenings picturesque. Not too far from St Michael's - Fool's Lantern is a definite must-visit spot.
Stayed 4 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Well equiped kitchen. Wonderful views over the Bay. Beds were very comfy. If you could control the mosquitoes it would be heaven. Everyone had a fantastic stay and would definitely come again. My son fell in love with the couches by the way.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

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

Perfect for our family!

Was on Tilghman for my son’s wedding. The house very comfortable, clean and a lot of thought was put in for making sure we had what we needed.
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

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

The view!!!

Much better than the description. The view is mesmerizing. House is very comfortable and our 3 year old grandson had a blast inside and out! Would gladly stay there again!
Stayed 3 nights in Jun 2024
Verified review

10/10 Excellent

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

Fabulous house for family in a wonderful spot!

We loved this house! It was very well stocked with everything we could have thought we needed. The layout of the house was perfect for our 6 adults and 1 toddler - much open space to enjoy each other's company as well as some more secluded, private spaces for quiet time. We all enjoyed ourselves immensely and we would highly recommend to others!
Stayed 7 nights in Aug 2023
Verified review

8/10 Good

Liked: Cleanliness, location, listing accuracy

Wedding Weekend

This property is lovely. It is spacious and sparkling clean, with plenty of room to spread out. For folks spending more time on Tilghman Island, the huge yard is wonderful. The kitchen has everything you need to enjoy your stay. And, for us, the location was perfect for the wedding venue but still easy access to St. Michaels.
Stayed 3 nights in Sep 2024
Verified review

10/10 Excellent

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

Best house on the Island!

This is the 2nd time we've rented this home and it felt like coming home! The layout is perfect, with lots of common area space. We loved watching the sunset, sitting on the dock and gazing at the stars at night. It is well stocked with thoughtful touches and amenities (soap, tissues, shampoo) and the house is well maintained!
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

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

Change of Pace

I have stayed at rentals all over; most recently in Japan. "10 Mile View," exactly as portrayed in its VRBO listing, is now a week captured as a cherished memory of outstanding sunrises and sunsets, puzzle building, crabbing and further family bonding. Thank you, Jennifer.
Stayed 7 nights in Aug 2023
Verified review

10/10 Excellent

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

AMAZING!

Just today back from my vacation at this amazing property, and my wife and I are already looking at the calendar to plan another visit! Wonderful, home, immaculately clean, thoughtfully and thoroughly appointed with million dollar views! Morning bald eagle visits (and ospreys all day), swimming all day, yard and deck relaxation in the evening along with fishing off the dock, and puzzles at night! Tilghman on the whole is an amazing place to unwind! Host communication is thorough and thoughtful. Without a the best rental I've stayed in in many years. If anything the listing understates how fantastic this home and area is!
Stayed 4 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
If you’re looking to escape the city you found the perfect place. The backyard views are incredible and it’s so peaceful out there. Tons of seating options if you have a bigger crowd. We had a girls trip with the ladies in the family and it was the perfect spot for us. It was too cold to use the pool when we were there but we spent a good portion of our time out in the backyard so we could soak up the views. We went into St Michael’s (about a 20 min drive) for dinners. The Ruse is a favorite of ours - get the burger and a Speedo and you’ll still be thinking about it a year later. Two If By Sea is a diner a couple minutes up the road with great food! If you’re looking for something a bit more secluded and quiet this house is perfect. Wish I could be back there now!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

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

Peaceful shore weekend

We love the comfort of the home with easy biking and a few breakfast options nearby.
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

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

Lovely Property

Comfortable and spacious together with the beautiful views made this an enjoyable long weekend with family.
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

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

Beautiful, quiet location & thoughtfully detailed!

Absolutely loved this place! The home and kitchen were well stocked, with thoughtful touches - we could find everything that we needed to cook multi-course meals and to serve them graciously!
Stayed 3 nights in Oct 2022
Verified review

10/10 Excellent

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

Waterfront WOW!

Best appointed property I have ever stayed in....... period. There wasn't anything we could think of that wasn't already provided. Amazing views of the bay and sunsets.
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

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

We had a blast live the house

It was amazing
Stayed 3 nights in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful well kept property. Fully stocked kitchen. Comfy beds. Quiet street. Magical views of the bay. Enjoyed sitting on the dock and the large deck watching the wildlife. Spacious house for folks to spread out for quiet time or all gather and be together. Highly recommend to friends and family.
Stayed 4 nights in Jun 2025
Verified review

10/10 Excellent

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

Beautiful Water View

This home is beautiful inside and outside. It is definitely in our top 3 for rentals. It is very comfortable and spacious. The deck is large and a great place to relax near the water. Our host was very responsive and made sure we had everything we needed. We definitely revisit this home.
Stayed 3 nights in Dec 2022
Verified review

10/10 Excellent

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

Great property right on the water in Tilghman Island!

We were visiting family who have a house on Tilghman, so we only used the house for sleeping, breakfast and showering in late afternoon before heading back to our family’s house. The views were fantastic and the house is very spacious and the air conditioning worked great. The house was exactly as advertised and the communication with the property manager was very good. A couple things that we would suggest that they could improve on: 1) there were exactly 8 bath towels for the 8 of us. There were also no beach towels provided. So know that ahead of time! It would have been nice if there could have been at least 1.5 towers per person. 2) there were no toiletries provided. Most rental homes that i have stayed in provide at least basic shampoo, conditioner and body soap. This house does not provide and I think providing these things is very helpful! 3) this would have been a nice to have, but the blinds don’t do much to keep the bedrooms dark. We were there early July, when the sun goes down late and comes up early! (Most rentals that I stay in do not provide this - but if you are coming with you children - be prepared!) 4) another nice to have would be 11 am checkout (I do recognize that this is often because cleaning crews need enough time to clean before the next guests - but 10 am checkout was hard for us!) We would definitely stay there again, but be more prepared for the items mentioned above!
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome host, great property. Will certainly be back!
Stayed 5 nights in Jun 2026