Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
21 min drive
Rooms & beds
4 bedrooms (sleeps 12)
Basement Guestroom
1 Queen Bed
KIds Bunk Room
2 Single Bunk Beds
Main Floor Queen Guestroom 2
1 Queen Bed
Main Floor Queen Guest Room 1
1 Queen Bed
Master Bedroom
1 King Bed
3 bathrooms
Lower Level Hall
Toilet · Shower only
Main Floor Hall
Toilet · Shower only
Main Floor Master
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Balcony
Number of living rooms
Garden
About this property
2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Crownsville
Located on the waterfront, this holiday home is in Arden-on-the-Severn, a neighbourhood in Crownsville. Ballet Theater of Maryland and ARTFX Gallery of Fine Crafts and Arts are cultural highlights, and travellers looking to shop may want to visit Arundel Mills Mall and Westfield Annapolis Mall. Travelling with kids? Consider Maryland Renaissance Festival and Annapolis Bowl.
Maryland Renaissance Festival - 11 min drive - 15.1 km
Westfield Annapolis Mall - 15 min drive - 20.7 km
Annapolis Mall Shopping Center - 15 min drive - 20.7 km
Getting around
Odenton Station - 21 min drive
Baltimore Washington International Airport (BWI) - 32 min drive
Restaurants
McDonald's - 18 min drive
Gina's Cantina - 9 min drive
Rise Up Coffee - 18 min drive
Little Carmine's N.Y. Pizza Kitchen - 15 min drive
Dunkin' - 11 min drive
Frequently asked questions
Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
As of 13 Apr 2026, prices found for a 1-night stay for 2 adults at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free on 13 May 2026 start from £704, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
On-site parking is available at the property.
What time is check-in at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
Check-in begins at 4:00 PM.
What time is check-out at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?
Checkout is at 11:00 AM.
Where is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free located?
Located on the waterfront, this family-friendly holiday home is within 9 mi (15 km) of Joyces Marina, Maryland Renaissance Festival and Annapolis Bowl. Westfield Annapolis Mall and Annapolis Mall Shopping Center are also within 9 miles (15 km).
Reviews
9.8
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Thanks, Lydia! We’re thrilled to hear that The Jolly Roger impressed you with its incredible view. We hope to host you again next time you’re in town!
Melissa~iTrip Annapolis
We had a great experience staying at the Jolly Roger. The house was unique and was everything we had hoped for! I’m sure we’ll stay there again in the future!
Joe H.
Stayed 9 nights in Aug 2023
Response from VrboOwner on 24 Oct 2023
Thank you Joe! We would love to welcome you back to The Jolly Roger anytime. Safe Travels!
-Tiffany
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.
Peter N.
Stayed 4 nights in Oct 2024
Response from VrboOwner on 11 Oct 2024
Hi Peter! Thank you for being a great guest & we welcome you back anytime! Thank you for sharing your positive feedback, we sincerely appreciate knowing you enjoyed your time in the home, Melissa~iTripAnnapolis
We had a great time! It was wonderful to be able to prepare meals in the well appointed kitchen and play ping pong during the rainy times. We also enjoyed the deck and the dock. I would highly recommend this for a family getaway!
Treva G.
Stayed 3 nights in Jun 2023
Response from VrboOwner on 29 Jun 2023
Thank you Treva for your kind review of The Jolly Roger. We would love the opportunity to host you again. Safe Travels!
-Tiffany
The pictures do not di justice to the besuty if the house and its location. The house has everything we needed for our big group of 10 people. Looking forward to staying here again.
Shankari S.
Stayed 3 nights in Aug 2023
Response from VrboOwner on 30 Aug 2023
Thank you for your kind review of The Jolly Roger. We look forward to hosting you again. Safe Travels!
-Tiffany
From a partner site
10/10 Excellent
Kirra E.
3 Jul 2023
Stay at the Jolly Roger
Home was so pretty and view was even better! We enjoyed the on-site paddle boards & kayaks. Girls trip was a success. Thank you!
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!
Camilla M.
Stayed 3 nights in Aug 2024
Response from VrboOwner on 27 Aug 2024
Thank you for staying with us, Camilla & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Wonderful home for a family gathering. We felt like we were staying with family as the house has a very lived in home feeling. We enjoyed all the activities offered but our favorite was sitting on the deck enjoying the view and each other's company.
Maria B.
Stayed 4 nights in Sep 2022
Response from VrboOwner on 7 Oct 2022
Thanks, Maria! Come back and stay with us again any time.
Sean
From a partner site
10/10 Excellent
Jim C.
5 Jul 2024
Family vacation
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
Jim C.
Stayed 3 nights in Jun 2024
Response from VrboOwner on 6 Jul 2024
Thank you for staying with us Jim & for your positive feedback! We welcome you back anytime! Melissa~iTripAnnapolis
Nice, comfortable place to stay with a large family group! Water views are beautiful. House had all the amenities you will need for a comfortable stay! Would like to stay during warm summer months to enjoy the water activities. Close to Baltimore, Annapolis and BWI.
Verified traveller
Stayed 4 nights in Nov 2022
Response from VrboOwner on 15 Dec 2022
Thank you for the wonderful review of The Jolly Roger Nancy. We are so happy to hear you enjoyed your stay. We look forward to welcoming you back anytime.
-Tiffany
Beautiful views, quiet location. Enjoyed watching the birds with our dog. Primary bedroom - comfortable large bed and very nice bathroom. Our son loved playing ping pong and foosball downstairs.
Alyssa A.
Stayed 2 nights in Mar 2024
Response from VrboOwner on 29 Mar 2024
Thank you for allowing us to host your stay Alyssa & we welcome you back anytime! Melissa~iTripAnnapolis
Verified
6/10 Okay
Mary Kate H.
20 Apr 2025
Liked: Check-in, communication, location
Disliked: Cleanliness
Lived in with lovely views
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.
House was very well equipped for all. Kids (toys) to adults (outdoor seating, dock , kayaks). Most definitely recommend for large gatherings
Walter G.
Stayed 2 nights in Nov 2023
Response from VrboOwner on 24 Nov 2023
Thanks, Walter! Glad you enjoyed everything. Please come back again!
Sean
From a partner site
10/10 Excellent
Kimberly G.
13 Jul 2023
Family getaway
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 G.
Stayed 6 nights in Jun 2023
Response from VrboOwner on 19 Jul 2023
Thank you Kimberly for your kind review of The Jolly Roger. We hope you enjoyed your stay. We appreciate your feedback as we are always striving to improve out properties. Safe Travels!
-Tiffany
Attended the Annapolis boat show. Location was a quick drive to downtown Annapolis
House had everything you could ask for and more. Spectacular sunsets and a very quiet neighborhood. Would highly recommend. Just a beautiful home
Betty M.
Stayed 2 nights in Oct 2022
Response from VrboOwner on 11 Nov 2022
Hello Betty! We really hope you will come back and stay with iTrip Vacations Annapolis and The Jolly Roger again! - Cathy
Thank you for your review of The Jolly Roger. Please come back and stay with us again. Safe Travels!
-Tiffany
From a partner site
10/10 Excellent
Sarah W.
7 Apr 2024
Spring break vacay
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 W.
Stayed 3 nights in Apr 2024
Response from VrboOwner on 9 Apr 2024
Hi Sarah! Thank you for your positive feedback! We welcome you back anytime, thank you, Melissa~iTripAnnapolis
Our family met in Maryland for a family funeral - and we booked the Jolly Roger, so we could all stay together. This place was FABULOUS - gorgeous views, plenty of room for us to be together and also have some alone time. We had some family visit with little kids and there were plenty of toys, a foosball table and ping pong table that kept them entertained. Truly, the house was the highlight of our trip. A number of people said they'd like to rent it again!
Suzanne H.
Stayed 4 nights in Mar 2024
Response from VrboOwner on 13 Mar 2024
Thank you for allowing us to host your stay Suzanne & we welcome you back anytime!
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!!
This property is great for extended families. The layout offers places to gather as well as options for alone time. The kitchen is extremely well stocked. High quality sheets and towels are provided. Young children are accommodated with high chairs and toys. Ping pong, foosball, kayaking, paddle boarding, canoeing, and fishing can keep guests entertained. Close (15ish minutes) to Annapolis and BWI.
Teresa S.
Stayed 4 nights in Oct 2023
Response from VrboOwner on 26 Oct 2023
Thanks, Teresa! We’d love to have you back again next time you’re coming to the area.
Sean
From a partner site
10/10 Excellent
Crystal S.
19 Oct 2021
The porch is to die for!
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 S.
Response from VrboOwner on 22 Oct 2021
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
About the host
Hosted by iTrip Vacations Annapolis - Sean Degnan
Languages:
English
Premier Host
They consistently provide great experiences for their guests