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Private Pier Waterfront Jolly Roger mins to DTA

From

$950
/ night
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

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From

$950
/ night

About this property

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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  • Pet Friendly

  • Refrigerator

  • Cable / Satellite TV

  • Microwave

  • Hair Dryer

  • DVD Player

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Location

Crownsville, Maryland

Guest reviews

10

Lydia W.

VRB-logo

Oct 8, 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

Jun 23, 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

Apr 20, 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.

VRB-logo

Oct 9, 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.

VRB-logo

Aug 20, 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!

Property Policies

Check-in instructions

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

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Check-in

Check-out

Check-in from 16:00

Before 11:00


FAQs about Private Pier Waterfront Jolly Roger mins to DTA

Is parking available at the property?

Parking is available on-site in the driveway, accommodating multiple cars.


Are pets allowed at the property?

Pets are allowed with a non-refundable fee of $150 paid prior to check-in. Service animals are exempt from this fee.


What are the check-in and check-out times?

Check-in is at 16:00 and check-out is at 11:00. Early or late check-in/check-out may be available upon request.


What accessibility features does the property have?

The property features step-free entrances and wheelchair-accessible facilities, including public areas and bathrooms.

What is the location of the property in relation to key landmarks?

The property is located on the waterfront in Arden-on-the-Severn, approximately 13 miles from downtown Annapolis and the U.S. Naval Academy, and 32 miles from Washington, DC.


Are children allowed at the property?

Children are allowed at the property, with no additional charge for ages 0-17.


What are the policies for extra beds and cribs?

The property does not provide cribs or extra beds. It accommodates a maximum of 12 guests, including children.


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