The Jolly Roger

4 BR
3 Baths
Sleeps 12


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


-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


-Adult and kid kayaks (Life jackets provided)

-Lower level recreation room with foosball and ping pong tables 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

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/no pets. 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.

1148 Severnview Dr Crownsville, MD 21032
Registration Number: 000327

Sleeping Arrangements

Master Bedroom King
Main Floor Queen Guest Room 1 Queen
Main Floor Queen Guestroom 2 Queen
Basement Guestroom Queen
KIds Bunk Room Bunk Twin (2)

Bathroom Configuration

Main Floor Master: Shower, Toilet
Main Floor Hall: Shower, Toilet
Lower Level Hall: Shower, Toilet

Property Rules

Check In: After 4pm
Check Out: Before 11am
Smoking: Not Allowed


Air Conditioning
BBQ Grill
Bath Towels
Bed Linens
Big Screen TV
Carbon Monoxide Detector
Clothes Dryer
Coffee Maker
Cooking basics
Covered Patio
Dining room
Enhanced Cleaning
Full Kitchen
Hair Dryer
Ice Maker
Internet Access
Iron and Board
Living room
Open Patio
Parking Available
Pets Considered
Ping Pong
Private Backyard
Private Fishing Pier
Private Pier
Private entrance
Satellite or Cable
Self Check-In
Smoke Detector
Smoke alarms
Travel crib
Washing Machine
Water View
body wash
hot water
outdoor Fireplace
portable crib



Frequently Asked Questions


Tenant is at least 25 years old and will be an occupant of the unit The Jolly Roger. Should any unauthorized persons occupy or use the Premises, Tenant shall vacate the premises immediately without any refund.


Balance is due 30 days prior to arrival date and includes a refundable damage deposit. The balance is due on _BalanceDueDate_. Payment may be made by major credit card. 


Cancellations must occur at least 30 days prior to arrival date, or WILL BE CHARGED THE FULL AMOUNT. If cancellation occurs 30 days or more prior to arrival date all monies will be refunded with the exception of a $100.00 administrative fee.


No BBQ grills of any kind are permitted in the unit. No open flames permitted in the unit.


If you wish to bring your dog, you will need to pay the $150 non-refundable pet deposit per pet prior to arrival.  If you bring an unathorized pet on to the property, you will be asked to vacate immediately with no refund of rent or damage deposit. Homeowner and Agent assume no responsibility for any illness or injury that may occur to pets or humans while on the premises. Homeowner and Agent assume no responsibility for the behavior of the pet(s); that responsibility is the Tenant owner.


Any reservation obtained under false pretense will be subject to forfeiture of reservation deposit, damage deposit, and/or balance of rental payment.


There is no daily maid service. Linens and towels are included and not to be taken from the unit. There is a $_CleaningFee_ one time cleaning fee.


No compensation will be given for temporary outage of electricity, gas, water or cable. 


Your damage deposit will be forfeited and you will incur an additional charge for cleaning and deodorizing if any evidence of smoking is found.


Owner or owner's agents may enter the premises: in case of an emergency; to make any necessary or agreed upon repairs, alterations, or improvements; supply necessary or agreed upon services or show the premises to prospective purchasers, renters or contractors.  24 hours notice of Owners intent to enter will be given (except in the case of an emergency).


  1. Tenant agrees to leave the premises and its contents in the same condition, neat and tidy, as Tenant found the premises to be upon move-in, normal wear and tear expected. Please leave all used towels on the floors of the bathrooms and beds linens should all be left on each bed for housekeeping.
  2. All dishes are to be washed and all garbage removed from the premises and placed in outside receptacles. If these items are not completed, the guest will be charged an additional cleaning fee. 
  3. The maximum number of occupants shall not exceed 12 people, not including a child in a crib.
  4. Furnishings are not to be removed from the premises for use outside or in other properties.
  5. No Smoking.
  6. Reservations are not made by or for a minor, defined as any person under the age of 25.
  7. Tenant and any guest of Tenant shall obey all laws of the state of Maryland, as well as local laws, at all times while they are on the premises. Failure to abide by the laws of Maryland or the above rules may cause tenant to be asked to vacate the premises and forfeit all rents and security/damage deposits.
  8. All noise must be brought inside by 10pm. Failure to do so could result in a $500 fine.


Tenant and all other occupants will be required to vacate the premises and forfeit the rental fee and security deposit for: Occupancy exceeding the sleeping capacity of 12 people, using the premises for illegal activity, causing damage to the premises rented or to any of the neighboring properties and any other acts which interferes with neighbors' right to quiet enjoyment of their premises.


iTrip or the Owner, does not assume any liability for loss, damage or injury to persons or their personal property. Neither does owner accept any liability for any inconveniences, damage, loss or injury arising from any temporary defects or stoppage in supply of water, gas, cable service, electricity or plumbing, as well as due to weather conditions, natural disasters, acts of God, or other reasons beyond its control.


Please report any maintenance needs for the premises to the us and we will respond as quickly as possible. Refunds will not be made for maintenance issues including, but not limited to heating and air conditioning, appliances, televisions, and stereos.


Delightful, picturesque home on the river.
5/5 stars
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.
- Angela

Hi Angela- Thank you for your positive feedback & for letting us know you enjoyed your stay! Guests like yourself & your happiness, mean the world to us & we welcome you back to stay again, anytime! Melissa~iTripAnnapolis

- Manager Response
Spring break vacay
5/5 stars
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!
- Sarah

Hi Sarah! Thank you for your positive feedback & we are thrilled to know you enjoyed your stay! We welcome you back anytime, thank you, Melissa~iTripAnnapolis

- Manager Response
Snowed in
4/5 stars
"Overall, the vacation rental house was stunning with a modern kitchen that was fully equipped. Unfortunately, the deck wasn't cleared of snow, but the basement made up for it with a fantastic play area, including a ping pong table, toys, board games, and books. Despite the snow, we managed to barbecue. However, the lack of snow removal was disappointing, none of us had a shovel, and we couldn’t find one in the house, so it was a lot of manual snow removal in the entrance and sidewalk. The deck was too match to remove by hand. We hoped for a better response from the rental company, especially since check in was at 4 pm, enough time to clean some of it. We also wished for some leniency with the check-out time due to the heavy snowfall, but were instead charged an extra fee to stay two hours longer. The experience was lovely, but the snow removal issue was a bit disappointing. All in all, we had a great time, the view is spectacular and would recommend staying here, especially if you have a big family, just make sure there’s no snow in the forecast!
- Sil
5/5 stars
Jolly Roger was perfect for family holiday. The Fall foilage views were breathtaking from the deck and dock. The location was so convienient for day tripping.
- Mary
Family getaway
5/5 stars
House was nice and as-advertised. Beautiful view. Only thing to note are the many steps down to the dock which were not possible for an elderly parent, and the bunk beds are not in a room.
- Kimberly
Great Family Geyaway
5/5 stars
We rented the Jolly Roger in Annapolis to celebrate my daughter’s birthday. We had several of her cousins and 2 aunts join us. The house had a well appointed kitchen - we love to cook as a family. Despite the rain we all had a wonderful time. We played ping pong and even sat on the dock in the rain. Will definitely consider staying again next year!
- Treva
Stay at the Jolly Roger
5/5 stars
Home was so pretty and view was even better! We enjoyed the on-site paddle boards & kayaks. Girls trip was a success. Thank you!
- Kirra
Beautiful River View
5/5 stars
This house was very comfortable and had all the amenities to host a large family group. The view of the river was spectacular! It was November while we were there and couldn’t enjoy summer water as activities. We did, though, use the fire pit which was nice on a cool evening. We may come again.
- Nancy
Great Family Rental
5/5 stars
We just completed Thanksgiving at the Jolly Roger so we could spend the holiday with our Midshipman. We had 9 people at the house comfortably. The house is situated about halfway in between BWI and Annapolis - which is very convenient if you have folks flying in and out at different times. It sits beautifully on the Severn River. The morning views are fantastic. The house is clean and well-appointed. It is very roomy inside, so don't let the streetview concern you. We also found the management company proactive and responsive. This won't be our last time staying there.
- Rob
The porch is to die for!
5/5 stars
We spent 99% of our time on the back porch-we ate there, played there, and chatted. Great accommodations on the porch. The company was easy to work with and quick with communication. I would highly recommend renting a boat and keeping it at the dock. It was the highlight of the trip! Uber was not as accessible as we had hoped so I would rent a car if we visit again.
- Crystal

Thank you Crystal for your kind words! We are so very happy you had a lovely time at the Jolly Roger! Please come back and visit us again anytime! Cathy

- Manager Response

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Contact Manager

Phone (410) 571-4076