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Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels

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TV, offices - Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels (Tilghman Island)
Minutes from St. Michaels, this waterfront home offers a perfect vacation experience with panoramic views of the water and exciting activities like kayaking and fishing from the dock. Relax in the pool, unwind at the waterfront firepit on starry nights or rejuvenate in the hot tub.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathrooms

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels

Summary:

Wake up to sweeping waterfront views, spend your days crabbing from your private dock, kayaking along the shore, or lounging by the pool with a good book. Just minutes from charming St. Michaels, this 4-bedroom retreat blends coastal charm with modern comfort — perfect for families, friends, or a romantic getaway.



In the evenings, grill, gather around the firepit under the stars, and let the day fade away in the bubbling hot tub. Guests love the spacious layout, the dreamy screened-in porch for morning coffee, and the unbeatable sunsets right from the deck.



Talbot County Licensure: STRN-24-62.



The Space:

This stunning 4-bedroom, 3-bath waterfront property is your gateway to relaxation, adventure, and unforgettable memories. Just minutes from St. Michaels, it offers panoramic water views, a private dock, and a pool overlooking the bay.



What you'll love:

- Private dock for crabbing, fishing, kayaking, or paddleboarding

- Pool and hot tub for year-round enjoyment

- Fire pit with Adirondack chairs for cozy nights under the stars

- Screened-in porch for coffee at sunrise or wine at sunset

- Spacious layout with gourmet kitchen — perfect for family feasts



Whether you’re here for a summer getaway, a fall foliage retreat, or a quiet winter escape, this home offers everything you need for a perfect stay.



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:

Located in a peaceful waterfront community, yet just minutes from shops, restaurants, and boat tours in St. Michaels. Enjoy biking, local wineries, and fresh seafood year-round.



Getting Around:

Easily explore by car, bike, or on foot. Cyclists will love the scenic rides, and the property offers a secure area to store bikes.



Other Things to Note:

Ideal for year-round getaways — cozy by the fireplace in winter, breezy sunsets in summer

We supply a starter supply of toilet paper and paper towel.

We welcome your furry friends for a nonrefundable $200 pet deposit.



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

Property amenities

Pool/Spa

  • Communal pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4.5 bathrooms
  • Hair dryer
  • Shower
  • Towels provided

Entertainment

  • Games
  • TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • On a river
  • On the waterfront

Things to do

  • Bicycles
  • Boat
  • Optional golf privileges
  • 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)
  • Fire extinguisher

General

  • Bicycles
  • Garden

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9.4 out of 10, Exceptional, 764 reviews
The price is CA $255
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includes taxes & fees
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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 allowed
Service animals are welcome, and are exempt from fees
Note from host: Charge may apply

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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

About the area

Located in Tilghman, this vacation home is in a rural area and on the waterfront. Chesapeake Bay and Northern Chesapeake Bay reflect the area's natural beauty and area attractions include Phillips Wharf Environmental Center and Chesapeake Bay Maritime Museum. Chesapeake Beach Railway Museum and Chesapeake Beach Water Park 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 Vacation homes in Tilghman
Map
Tilghman Island, MD

What's nearby

  • Tilghman Watermen’s Museum
    7 min drive - 5.9 km
  • Talbot County Library Tilghman Branch
    7 min drive - 6.2 km
  • Kronsberg Park
    8 min drive - 6.6 km
  • Tilghman Island Marina
    8 min drive - 7.2 km
  • Phillips Wharf Environmental Center
    9 min drive - 7.6 km

Getting around

  • Cambridge Station
    68 min drive
  • Easton, MD (ESN-Easton - Newnam)
    48 min drive

Restaurants

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

Frequently asked questions

Does Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels have a pool?

Yes, this property has a pool.

How much does it cost to stay at Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels?

As of Jun 3, 2026, prices found for a 1-night stay for 2 adults at Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels on Jun 11, 2026 start from CA $692, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels?

Check-out is at 10:00 AM.

Where is Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels located?

Situated on the waterfront, this vacation home is within 3 mi (5 km) of Tilghman Watermen’s Museum, Talbot County Library Tilghman Branch, and Chesapeake Bay. Northern Chesapeake Bay and Kronsberg Park are also within 3 mi (5 km).

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Waterfront Home with Pool, Hot Tub, Dock & Sunset Views – Near St. Michaels 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. 19 out of 19 reviews
Rating 8 - Good. 0 out of 19 reviews
Rating 6 - Okay. 0 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

9.8

Cleanliness

9.8

Location

Reviews

Verified

10/10 Excellent

Kathy B.

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

Amazing Waterfront Stay

Our family stayed here for Spring Break in April 2025. The property has amazing views, with a well stocked kitchen, pool, hot tub and lots of privacy. The wildlife was also incredible. We will definitely be back to enjoy this beautiful space on Tilghman Island.
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Dan A.

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

Great week!

We had an amazing time at this house, which is very spacious and exactly as reflected in the photos! Would highly recommend for a relaxing week a little away from everything, but not too far!
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Elizabeth P.

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

Superb property

Wonderful property and such a beautiful location. The home is so well equipped (the best stocked kitchen in a rental!) and the beds were unbelievably comfortable! Jennifer and the team at Flaneur were so helpful in the lead up to our stay and answered all of our questions really quickly. We would not hesitate to recommend this property to others.
Stayed 7 nights in Sep 2024
Verified

10/10 Excellent

Kevin

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

Our Tilghman Island Getaway

My wife and I spent a fabulous weekend with 3 other couples at this Tilghman Island property. The property has amazing waterfront views and a large dock. Our VRBO agent, Jennifer Brown was very helpful and quick to respond to questions and requests.
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Sandra K.

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

Beautiful view

We had a wonderful time in Tilghman and particularly at this house. The setting and home were better than we expected. The house was clean, comfortable and provided everything we needed. The view was amazing and we were also able to enjoy the pool. We were in the area for a wedding so didn’t get to enjoy the house as a destination but planning to return again for just thst.
Stayed 3 nights in Sep 2024
Verified

10/10 Excellent

Robin S.

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

Peaceful Breeze and Bay Sounds

We enjoyed our stay immensely. Five of us, friends since kindergarten, celebrating turning 60 this year. The house was very comfortable, especially the beds. We spent alot of time on the screened-in porch. Beautiful sun rises & sunsets. Only 10 miles to St. Michaels for shopping. porch.
Stayed 4 nights in Sep 2024
Verified

10/10 Excellent

Maria Q.

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

Lovely house at a fantastic destination!

What a great stay we had at this Tilghman Island retreat! The wide-open waterfront location, pool, and neatly laid out back yard was an instant sell for me, but the house itself had a great layout, updated local/coastal-themed decor, and tons of interesting material available to soak in and learn about the area. The house is about a 12 minute drive to/from St Michaels proper, so if peace and quiet with close proximity to the (laid back) action is your thing- as it is mine- this lovely home will suit you well. (The fact that they had coffee service available was a thoughtful touch too!) Thanks for a great and memorable stay!
Stayed 4 nights in Aug 2023
Verified

10/10 Excellent

Kathy P.

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

Solitude and Bliss

This house and property are every bit as nice as the pictures show. You will not regret staying in this home. The pool was incredible, the location is completely private. Our family of 6 adults had the best time.Plenty of room for multiple cooks in the kitchen. Every space is thoughtfully used. Watching the eagles every day was a highlight as they nest in the trees along the shore. We will definitely return to the area and to this home as it was perfect.
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Anita K.

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

Absolutely lovely

Stunning house and property is exactly as described. We were 5 adults and 4 kids with plenty of room. Heated pool and hot tub were clean and functioned well. Grounds are well manicured and we had fun throwing frisbees and flying kites. Caught a few crabs off the dock. Kitchen was well stocked with everything needed to cook. We did have a leaky toilet, but that was repaired quickly after reaching out to management. We all had a great time here.
Stayed 6 nights in Aug 2023
Verified

10/10 Excellent

Susan M.

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

Quiet getaway

Property & house very well maintained with beautiful views. Area is so peaceful with lots of wildlife. Hot tub & pool were awesome. We all had a relaxing stay & hated to leave.
Stayed 4 nights in May 2023
Verified

10/10 Excellent

Jorge R.

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

Beautiful home and location

My family of five had an amazing time at this home. It was the perfect size for a family of 5 to spread out and come together. We especially enjoyed the pool, hot tub, and screened porch. The grounds are gorgeous and the wildlife (birds) also kept us entertained.
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Sunny H.

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

Amazing Family Vacation

The property was perfect. Time seemed to stand still. We created so many wonderful memories. Looking forward to our return trip next summer, maybe even before!
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Monty G.

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

Awesome property. 3 side ocean. Very well maintained.

Awesome property. 3 side ocean. Very well maintained
Stayed 4 nights in Feb 2023
Verified

10/10 Excellent

Amy W.

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

Amazing views and so peaceful

This property was so beautiful. Panoramic views that were amazing. Sunrise and sunsets! The house was perfect! Clean, stocked and ready to go!
Stayed 4 nights in Mar 2023
Verified

10/10 Excellent

Sue M.

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

Family vacation

This house is the perfect getaway for relaxation, quiet and calm. It was large enough to house our family for the week. We enjoyed the pool and the hot tub and loved listening the water and watching the boats go by. The kitchen had everything you needed to cook in, if you wanted and enough full bath/bedrooms to give everyone their space!
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Verified traveller

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

fun stay

The house is nice, the property is beautiful. I think the cleaning service should have done a better job of vacuum cleaning, toilet scrubbing and washing the bath mats and more.
Stayed 7 nights in Aug 2023
Verified

10/10 Excellent

Nancy S.

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

Absolutely gorgeous & serene home

Our family of 4 stayed here for 4 nights in early June. Kids ages 18 & 23. This is the place to be for relaxation. The view is stupendous-water water everywhere. We came mainly to relax -but also to bike (we brought ours, but they are available to rent right at the house) & boat (2 thumbs up to Tilghman Island Marina-for boat rentals). The interior of the house is very nicely designed. We look forward to a return visit!
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Jerry B.

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

Perfect Getaway on the Bay

The property is spotlessly clean, comfortable and beautifully furnished. We took advantage of hikes along the bay and bird watching. The private dock equipped with picnic table (!) is perfect for fishing. It is a short drive to shopping, restaurants, and hiking trails in St. Michaels and Easton. The sunrise and sunset views are spectacular from all parts of the house. Jennifer was very helpful and responsive. We plan to return so we can use the pool, swim and kayak on the bay. This is one of the best vacation properties we've rented.
Stayed 6 nights in Dec 2022
Verified

10/10 Excellent

Laura B.

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

Beautiful Property

Beautiful home with gorgeous views of the bay. Perfect location for a quiet, relaxing weekend. Just what we needed to refresh and reset. Would absolutely stay again!
Stayed 3 nights in Oct 2022