Private Pier Waterfront Jolly Roger mins to DTA

Crownsville, Maryland
$1193 avg/night Minimum Stay 2 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

Night 2 nights

Min Stay

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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2400 Sq Ft (223 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Kitchen Island Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Firepit Garden Gas Grill Outdoor Furniture
  • BATHROOMS

    3 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Kayak On Site
  • ENTERTAINMENT

    Books DVD Player Foosball Table Games Table Tennis Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • LOCATION HIGHLIGHTS

    On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Rates & Availability

Review Review

  • Lydia W.

    Submitted Oct 8, 2025

    Stayed Oct 3, 2025

    Incredible view! We had a great time

  • Dr R Jeff S.

    Submitted Jun 23, 2025

    Stayed Jun 15, 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.

  • Mary Kate H.

    Submitted Apr 20, 2025

    Stayed Apr 17, 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.

  • Peter N.

    Submitted Oct 9, 2024

    Stayed Oct 2, 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.

  • Camilla M.

    Submitted Aug 20, 2024

    Stayed Aug 15, 2024

    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!

  • Linda H.

    Submitted Jul 8, 2024

    Stayed Jul 4, 2024

    This home has a beautiful deck, with a fantastic water view. The house has a well equipped kitchen, and updated bathrooms.

  • Jim C.

    Submitted Jul 5, 2024

    Stayed Jun 28, 2024

    We had a great time at the Jolly Rogers on the Severn. I trip was great to work with. Very professional. Place was beautiful right on the water. Lots to do for all ages. Perfect location. Highly recommend

  • A.J. S.

    Submitted Jun 5, 2024

    Stayed May 31, 2024

    We had a really nice stay in Crownsville. We took the time to visit D.C. and Baltimore on the way home, brought the ferry over on the way. We all took advantage of what the house had to offer kayaking, fishing, a nice fire the one night and cards and games out on the deck each night. The house and that view couldn't have been better. The process didn't ask for too much on the way in or the way out and that's nice for the price. A fun getaway for all!!

  • Angela w.

    Submitted May 31, 2024

    Stayed Dec 31, 1969

    We have rented many properties in the past, both from AB&B and VRBO. This home is unequivocally the most beautiful, the best kept, and the service the friendliest of any. From the booking process all the way until the final day the service was cordial, affable, and inviting. Many ads for properties and amenities must be taken with a grain of salt, but not The Jolly Roger. It easily slept 10 adults perfectly comfortably! It could easily sleep up to 12 as the ad describes, and if there are children, probably more. Like many in the area, we were there for the USNA commissioning week, so unfortunately we did not get to use the many amenities the home has, although we would have loved to. The drive to The Yard was easy even though the home itself is out-of-the-way and private. I could go on and on but trust me, this magnificent home was worth every penny. Unlike many rentals, they have cut no corners. Even the toilet paper is top notch, and I know that sounds silly, but I have stayed in many places that like to buy the wafer-thin public tp in bulk. There are more than enough extra towels and other bathroom amenities to go around and there are plenty of extra sheets, blankets, and pillows for extra bedding. Altogether, I would stay here 101 out of 100 times when next we have the opportunity. The nautical diving theme was an exotic cherry on top. Don't pass it by! I forgot to mention: plenty of easy parking as well.

  • Sarah W.

    Submitted Apr 7, 2024

    Stayed Apr 1, 2024

    It was a beautiful home to be in with many activities for my children along with my two gfs children. There was plenty to do to entertain our children as it rained for a few days. The view was quite breathtaking and the host was very accommodating to our needs. We will def be back! Thanks!

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Total

Includes taxes and fees
$1,193+
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