Captain's Cove

24692 Yacht Club Road
Saint Michaels, MD 21663
Popular! Recently viewed by 121 other travelers!

- New gazebo; restored barn w/ game room (open seasonally) - Gym & rowing equipment - Pool & pool house w/ kitchenette & full bathrooms - Hot tub (open year round) Talbot County STR License #ST-102-WEI






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Fantastic Family Compound Just 1/2 Mile to Historic District!

Located just on the outskirts of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway. The lovingly restored farmhouse has a brand new gourmet kitchen, five bedrooms, a cozy den, and a screened porch with a gas fireplace to warm you on those breezy summers or early fall mornings. There is plenty of room for everyone to spread out, play games, or enjoy coffee and plan the day while overlooking the formal garden.

The grounds are lush with mature landscaping, plenty of privacy, centuries-old shade trees, and room to roam for the little ones. Enjoy the new gazebo: a perfect backdrop to capture some treasured family photos! The newly restored barn supplies endless opportunities for your kids or kids-at-heart with game tables, air hockey, and foosball. Work off the crab cakes and ice cream with the Vectra gym and rowing equipment! The pool is flanked by a pool house complete with a changing area and two full baths for showering, in addition to a kitchenette for your snacks and favorite beverages. The hot tub is open year round for your enjoyment as well.

The deepwater slip has easy access to the Miles River and St. Michaels harbor. Kayaks are included with this property to explore the smaller creeks and nature-watch on a peaceful morning. Like a good Captain, the owner has taken meticulous care to ensure your enjoyment of this home. Guests who have previously stayed here will appreciate the continual upgrades, including new pool furniture, restored steps in the barn and other improvements. This home offers something for everyone!

Please note the ground floor of the barn is not available to guests between October and April.

Talbot County STR License #ST-102-WEI

Property Information & Notes

  • Koi Pond: This property has a koi pond. Please supervise young children!

  • Swimming Pool: Please note our swimming pools are open from May 15-October 15. Please be sure to bring your own pool towels

  • Hot Tub: Open Year Round

  • Waterfront: Long Haul Creek

  • Dock Information: 100 ft L-shaped dock with 6 ft MLW, water, electricity (30 amp). Please note the owner keeps sailboat at the long end of dock; guest slips are interior slips

  • Water Toys Included: 1 tandem kayak, 2 medium-sized kayaks (175 lbs or less), 1 stand up paddleboard

  • To ensure proper sizing for your group, please bring your own life jackets, or we can recommend a rental agency

  • Fireplace: Gas

  • Firepit: Firewood is not provided

  • Main house has 2.5 baths; Pool house has 2 baths

  • WiFi: Please note that the rural nature of the area limits the data access and some properties can experience slow speeds or access limited to email and web browsing and not streaming

  • Pet Policy: Pets Not Permitted

  • Grill: This property has a propane grill. Propane is provided


  • TVs in the living room, kids room, and game room

  • Stereo/Bose Radio

  • Barn with a home gym and game room with pool table. 1st level used for storage in off season, 2nd level still available. NO CENTRAL AIR/HEATING but has ceiling fan upstairs and furnace.

  • Only a half-mile to town proper of St. Michaels

Bed Sizes

  • Bedroom 1 - King

  • Bedroom 2 - Queen

  • Bedroom 3 - Double

  • Bedroom 4 - 2 Single

  • Bedroom 5 - 2 Single

Please Note:

All ESVR properties include 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 properties do not allow group rentals to guests under the age of 25. Therefore, online bookings for group rentals will not be honored.

Please Note: Weddings and special events of any kind are not permitted at our vacation rental properties due to local zoning ordinances and our homeowner agreements.

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



  • Kayaks # and Type = (1)tandem, 2 medium, 1 paddleboard
  • Internet Service = WiFi
  • Microwave = Yes
  • Central A/C = Yes
  • Coffee Maker = Yes
  • Dishwasher = Yes
  • Stove = Yes
  • Washer = Yes
  • Dryer = Yes
  • Location = Waterfront
  • Area = St. Michaels
  • Unit Type = Luxury
  • Non-Smoking = Yes
  • Rental Type = Saturday - Saturday
  • Pool Type = Private Outdoor Pool
  • Hot Tub / Jacuzzi = Yes
  • Boat Slip/Dock = Yes
  • Linens Provided = Yes
  • Pets Not Allowed = Yes
  • Oven = Yes
  • Heating = Yes
  • Towels = Yes
  • Dining Area = Yes
  • Smoke Detector = Yes
  • Waterfront = Creekfront
  • Water View = Creek View

Ask us about Mini Week Availability!

Period Nightly Weekly
07/24/2021 - 07/30/2021 $875 $6125
07/31/2021 - 08/06/2021 $875 $6125
08/07/2021 - 08/13/2021 $875 $6125
08/14/2021 - 08/20/2021 $875 $6125
08/21/2021 - 08/27/2021 $875 $6125
08/28/2021 - 09/03/2021 $875 $6125
09/04/2021 - 09/10/2021 $875 $6125
09/11/2021 - 09/17/2021 $875 $6125
09/18/2021 - 09/24/2021 $875 $6125
09/25/2021 - 10/01/2021 $875 $6125
10/02/2021 - 11/12/2021 $875 $6125
11/13/2021 - 11/19/2021 $875 $6125
11/20/2021 - 11/26/2021 $875 $6125
11/27/2021 - 12/24/2021 $875 $6125


We loved this place and have already rebooked for June 2021!
Captain's Cove is a gorgeous, beautifully furnished house with plenty of room for large families/groups. The property is huge and sprawling, with over 3 acres, so it feels very private. The bedrooms are spacious with the master on the first floor. We were there in July in a heat wave and can attest that the air conditioning works great. Lots of windows and light with great views down to the water. The kitchen is well equipped with Bosch appliances, a Subzero refrigerator and plenty of cookware and serving pieces. The laundry room also has a wine fridge and another small refrigerator which were well used during our visit. The property description and pictures don't do the pool house justice; it is a private little oasis on its own with a bedroom/queen bed, gorgeous full bath and separate half bath, plus a living room, small kitchenette and hot tub. We spent most of our time hanging out around the very large pool. It was too hot to use the gaming/gym space in the barn, but we did enjoy the bikes and kayaks. Our family group is already looking forward to our return next June. Thank you Eastern Shore!
Betty Uzupis
Oct 2020
Best Family Vacation Home!!!
Outstanding! Phenomenal! Perfect! Those words plus many more could describe our experience at the Captain's Cove. We had a family vacation there and it couldn't have been more wonderful! The home, yard, pool, pool house, hot tub, kayaks and barn had everyone of us fully taken care of. So many awesome amenities! We barely left the property! The memories made there are priceless. The entire booking process was a breeze and everyone was exceptional in their customer service. Our family will forever love and cherish our time there! Will HIGHLY recommend to everyone! THANK YOU!!!!
Erica Cooke
Jun 2020
Our family loved it.
This is the second vacation home we've rented through Vantage Vacations and we have been very pleased both times with our house and it's condition. Captain's Cove is a very lovely and large home on an inlet off the Miles River, adjacent to the Yacht Club. It has a swimming pool, dock, game room and basketball net in the barn, and lots of room for everyone to play and relax. There were kayaks and bicycles available for use.The house is beautifully decorated and comfortable. It is very conveniently located, near the shops and restaurants in St. Michaels, yet very private and quiet. Everyone in our three-generation family loved our vacation at Captain's Cove.
Richard Mason
Aug 2019
We loved this property!
We loved this property! It met all of our families needs! It was a gorgeous place, close to st. Michaels and lots to do right at the house! If it stays up for rent we would definitely love to rent this property again! I mostly worked with Sarah and she was very helpful.
Craig E.
Aug 2019
The place and location are magnificent!
Everything went very smoothly. It made our vacation more enjoyable. Friendly team members. There was anything and everything provided for the children and adults to do. It was really beyond our expectations. The owners were incredibly nice and helpful. It was simply perfect for our family. This property was simply gorgeous and just had everything you could want for an outstanding vacation. The game room was great! There was always something to do regardless of the weather. We also enjoyed the wildlife in the area, boating and the closeness to the town. This place was as perfect as it gets for our family. We will be back. 😊 The team members were very helpful and courteous. Everything went smoothly which made our vacation even more enjoyable.
Dixie Horst
Aug 2019
The whole process was very easy and smooth!
What a beautiful perfect house! Great location, beautiful but very comfortable furnishings---huge lawn, dock with gorgeous sailboat, tons of equipment (kayaks, paddle board, bikes) not to mention the game room and barn with basketball court! The owners were very friendly and available but also respected our privacy. Great kitchen and family room area. The pool house is ADORABLE--we had my mother-in-law with us and she moved in there right away. Our family loved this house--My husband is from Maryland so we had friends and family come over in the day to hang out and enjoy the amenities--it was perfect---very well equipped kitchen, room to spread out. Great TV room for watching movies in the evening or read on a rainy day. We biked into town every day--I went to Perry Cabin for a massage one day---truly a dreamy spot to set up camp on the eastern shore! Honestly besides a few emails back and forth I did not have much experience with the team which is actually a good thing in my book--I'm really busy working w family etc so I prefer that things are just taken care off quickly and easily without too much work!
Suzanne Goin
Jul 2019
5 star review
Judy Semler
Jul 2019
This was our second time staying at Captain's Cove
This was our second time staying at Captain's Cove. The property is absolutely wonderful, and I'd highly recommend it. The house is very comfortable and well-appointed. The proximity to downtown St. Michael's is perfect, and I can not say enough positive things about the amenities of this home. There is a fantastic game room in the adjacent outbuilding that is second-to-none. It will keep your family entertained for hours. There are plenty of kayaks and a paddleboard for use during your stay along with a large pool and hot tub. The pool house is wonderfully appointed and a nice addition of living space to the main farmhouse. In addition, there is a great selection of bikes to ride during your stay. I promise you that Captain's Cove will not disappoint! We have been visiting the Eastern Shore for many, many years and Captain's Cove is a premier property that will make your family's vacation perfect! Vantage Vacation Rentals was very easy to work with. They were responsive on the phone as well as via email regarding our reservation.
Stacey P.
Apr 2019
Everything went smoothly from booking, staying at the property and checkout. Very nice home with plenty of space and close to town.
Bradley Edwards
May 2018
Lovely well-maintained home and spacious enough for our large family! The newly renovated Pool House is gorgeous! Private setting, yet close enough to all the wonderful shops and restaurants in St. Michaels. Our kids enjoyed the pool, hot-tub, large yard and the barn-loft game room. The indoor sun room was a welcomed relief from the August heat with a large screen TV and, great air-conditioning throughout the entire house. The home-owners were very gracious and accommodating. Highly recommend 😊
Cynthia Tone
Feb 2018

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