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Private Pier Waterfront Jolly Roger mins to DTA - Image 1
Private Pier Waterfront Jolly Roger mins to DTA - Image 2
Private Pier Waterfront Jolly Roger mins to DTA - Image 3
Private Pier Waterfront Jolly Roger mins to DTA - Image 4
Private Pier Waterfront Jolly Roger mins to DTA - Image 5

Private Pier Waterfront Jolly Roger mins to DTA


Amenities

  • Pet Friendly

  • Refrigerator

  • Coffee / Tea Maker

  • Cable / Satellite TV

  • Microwave

  • Hair Dryer

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Property description

Experience the Difference: Professionally Managed by iTrip AnnapolisArrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is open to guests and offers many water sporting opportu...
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From

US$948
/ night

Guest reviews

10

Lydia W.

VRB-logo

8 Oct 2025

·

Stayed 2 nights

Incredible view! We had a great time
Incredible view! We had a great time

10

Dr R Jeff S.

VRB-logo

23 Jun 2025

·

Stayed -20,254 nights

The Jolly Roger is exactly as described. The view from the deck is even better than the pictures showed it to be. The beds are very comfortable. The kitchen is laid out well for three people to work in it at the same time and is well-equipped with any appliance we wanted. There were plenty of dishes and silverware for our family to use even when the dishwasher was running. The downstairs area was perfect for our grandchildren and has a good supply of games and foosball and ping pong tables. We had the misfortune of renting the house during two major storms so were not able to swim off the dock because of poor water quality. There are several kayaks and paddle boards, with many life jackets of varying sizes which were clean and in good shape. The outdoor swing was a a big hit. If we return to the area, we would definitely want to rent this property again.
The Jolly Roger is exactly as described. The view from the deck is even better than the pictures showed it to be. The beds are very comfortable. The kitchen is laid out well for three people to work in it at the same time and is well-equipped with any appliance we wanted. There were plenty of dishes and silverware for our family to use even when the dishwasher was running. The downstairs area was perfect for our grandchildren and has a good supply of games and foosball and ping pong tables. We had the misfortune of renting the house during two major storms so were not able to swim off the dock because of poor water quality. There are several kayaks and paddle boards, with many life jackets of varying sizes which were clean and in good shape. The outdoor swing was a a big hit. If we return to the area, we would definitely want to rent this property again.

6

Mary Kate H.

VRB-logo

20 Apr 2025

·

Stayed 3 nights

We booked the Jolly Roger for a group of about 10 family and friends to enjoy Easter weekend. The best part: the peaceful river views from the deck and dock access for kayaking and paddle boarding. It was really great for that: The house itself felt like it needed a thorough clean up and clean out. While charming—it felt like a home that has never been prepped or cleaned as a rental—it just felt like residents left their home quickly to rent it out for a few days.
We booked the Jolly Roger for a group of about 10 family and friends to enjoy Easter weekend. The best part: the peaceful river views from the deck and dock access for kayaking and paddle boarding. It was really great for that: The house itself felt like it needed a thorough clean up and clean out. While charming—it felt like a home that has never been prepped or cleaned as a rental—it just felt like residents left their home quickly to rent it out for a few days.

10

Peter N.

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9 Oct 2024

·

Stayed 4 nights

Great house for the family to get together. Plenty of toys and things to do on the property. Sitting on the deck as the sun went down was a big hit.
Great house for the family to get together. Plenty of toys and things to do on the property. Sitting on the deck as the sun went down was a big hit.

10

Camilla M.

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20 Aug 2024

·

Stayed 3 nights

My nuclear family stayed here for a big family reunion weekend that was also in Crownsville. Absolutely perfect stay! Close to where we needed to be, plenty of space and activities for our downtime. Spent tons of time kayaking with all of the provided equipment, able to cook multiple meals and all implements were provided. Will definitely come back!
My nuclear family stayed here for a big family reunion weekend that was also in Crownsville. Absolutely perfect stay! Close to where we needed to be, plenty of space and activities for our downtime. Spent tons of time kayaking with all of the provided equipment, able to cook multiple meals and all implements were provided. Will definitely come back!

Crownsville, Maryland

Location

Located on the waterfront, this vacation home is in Arden-on-the-Severn, a neighborhood in Crownsville. Ballet Theater of Maryland and Annapolis Civil Rights Plaque are cultural highlights, and travelers looking to shop may want to visit Arundel Mills Mall and Westfield Annapolis Mall. Traveling with kids? Consider Maryland Renaissance Festival and Annapolis Bowl.

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Property policies

Check-in instructions

Everything you need to know for a smooth check-in.

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Check-out

Check-in from 16:00

Before 11:00


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