Private Pier Waterfront Jolly Roger mins to DTA

Top rated by guests
Welcome to the Jolly Roger!
The gourmet kitchen overlooks the dining room and has great views of the water.
The gourmet kitchen's high end stainless steel appliances.
The bright gourmet kitchen opens up to the dining room.
Guests can park their boat at the owner's private pier (the one on the right).
review stars
10Outstanding
(34 Ratings)
"Incredible view! We had a great time "
Lydia W.
Don't miss out! Price and availability may change
10 / 10
Outstanding(34 Ratings)

House in Severna Park, MD

12 guests · 4 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

Experience the Difference: Professionally Managed by iTrip Annapolis

Arrive 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 opportunities during your stay! Nestled in the desirable quiet Arden on the Severn community. There are kids' and adult kayaks, canoes, stand-up paddle boards, fishing poles and crab traps. There are plenty of life jackets in the meticulous boat house. Sit on the back deck with unobstructed water views of the Severn River through the new glass railing. The deck has plenty of seating, a dining table and a gas grill.



Head inside the home to the living space on the main floor that stretches across the kitchen, family and dining rooms - all with MILLION DOLLAR WATER VIEWS. The Main Floor Master Bedroom has a King bed (split with individual controls), master bath with multiple shower heads, a bidet and a walk-in closet. There are two more guest rooms on the main floor with Queen beds that share a full bath in the hall.



The lower level is perfect for families with a large guest room with Queen Bed, a full bath and bunks for 4 kids or teens. Additional outdoor living space includes a large back yard, downstairs covered patio and a built-in firepit. The home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis.



SLEEPING ARRANGEMENTS 4 BR / 3 BA / Sleeps 8 adults and 4 kids/teens in bunks:

Main Floor Suite:

-King bed (Split with individual controls)

-Private Bathroom with Shower, bidet and vanity

-Large walk-in closet



Bedroom 1 on Main Floor:

-Queen bed

-Full Hall Bath



Bedroom 2 on Main Floor:

-Queen bed

-Full Hall Bath



Bedroom on lower level:

-Queen Bed

-Full Hall Bath



Bunk Room on lower level

-2 Bunks (4 Twin beds)

-Full Hall Bath



HIGHLIGHTS:

-Wrap-around deck with glass railing and water views a dining table and plenty of seating

-Water access from private pier on the Severn River

-BBQ Gas grill (propane tank provided)

-Spacious kitchen with stainless steel appliances

-Covered Patio on lower level

-Firepit

-Adult and kid kayaks (Life jackets provided)

-Lower level recreation room with foosball and indoor/outdoor ping pong table and TV

-Dining room table seats 10-12

-High Speed Internet and WiFi

-Smart Flatscreen TV's

-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service

-Parking for multiple cars in driveway

-Full Laundry room with washer & dryer located inside the home

-Dogs allowed with $150 non-refundable fee paid prior to checkin



Property Distance to:

-Downtown Annapolis – 13 miles

-U.S. Naval Academy – 13 miles

-Washington, DC – 32 miles

-Baltimore - 25 miles



*Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid.

* All beds are made for you with freshly-laundered sheets & towels.



House Rules

Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.

Amenities at Private Pier Waterfront Jolly Roger mins to DTA

Non-smoking
Pets allowed
Family friendly

Map of Severna Park, MD


Ratings and reviews

10 / 10
Outstanding(34 Ratings)
10 / 10Outstanding·Oct 2025
Incredible view! We had a great time
10 / 10Outstanding·Jun 2025
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.
10 / 10Outstanding·Oct 2024
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.
6 / 10Average·Apr 2025
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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Private Pier Waterfront Jolly Roger mins to DTA. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Private Pier Waterfront Jolly Roger mins to DTA pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Private Pier Waterfront Jolly Roger mins to DTA?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.