Private Pier Waterfront Jolly Roger mins to DTA

Photo gallery for Private Pier Waterfront Jolly Roger mins to DTA

A wooden deck leading to a lake, surrounded by trees and a wooden fence.
A marina with boats docked, surrounded by trees and a clear sky.
A modern two-story house with a glass balcony, a covered patio, and a well-maintained garden.
A spacious living room with a large window overlooking a body of water, a ceiling fan, and a dining area with wooden furniture.
An outdoor deck with a wooden table and chairs, wicker sofas, and a glass railing overlooking a lake with boats.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • Ping pong on-site
    A rare find — challenge friends and family to endless matches.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Barbecue grill
  • Free Wi-Fi
  • Air-conditioning
  • Kitchen
  • Pet-friendly

Explore the area

View in a map
Crownsville, MD
  • Place, Joyces Marina
    ‪10 min drive‬
  • Place, Maryland Renaissance Festival
    ‪13 min drive‬
  • Place, Annapolis Mall Shopping Center
    ‪16 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪26 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

Add dates for prices

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About the area

Crownsville

Located on the waterfront, this holiday home is in Arden-on-the-Severn, a neighbourhood in Crownsville. Travellers who have shopping on the agenda can visit Annapolis City Dock and Arundel Mills Mall. Travelling with kids? Consider Maryland Renaissance Festival and Annapolis Bowl.
View more Holiday homes in CrownsvilleOpens in a new window
Map
Crownsville, MD

What's nearby

  • Joyces Marina - 10 min drive - 9.3 km
  • Maryland Renaissance Festival - 13 min drive - 15.5 km
  • Annapolis Bowl - 15 min drive - 17.6 km
  • Annapolis Mall Shopping Center - 16 min drive - 18.3 km
  • Annapolis Harbor Center Shopping Center - 19 min drive - 22.7 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
  • ‪Dunkin' - ‬11 min drive
  • ‪7-Eleven - ‬15 min drive
  • ‪Little Carmine's N.Y. Pizza Kitchen - ‬15 min drive

Frequently asked questions

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

Yes, pets are allowed at this property.

How much is parking at Private Pier Waterfront Jolly Roger mins to DTA?

On-site parking is available at the property.

What time is check-in at Private Pier Waterfront Jolly Roger mins to DTA?

Check-in begins at 4:00 PM.

What time is check-out at Private Pier Waterfront Jolly Roger mins to DTA?

Checkout is at 11:00 AM.

Where is Private Pier Waterfront Jolly Roger mins to DTA 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. Annapolis Mall Shopping Center and B&A Trail 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 32 out of 35 reviews
Rating 8 - Good. 1 out of 35 reviews
Rating 6 - Okay. 2 out of 35 reviews
Rating 4 - Poor. 0 out of 35 reviews
Rating 2 - Terrible. 0 out of 35 reviews

9.6/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Incredible view! We had a great time
Stayed 2 nights in Oct 2025
Response from VrboOwner on 14 Oct 2025
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

The house was well equipped and the views were amazing.
Stayed 3 nights in Sep 2023
Response from VrboOwner on 7 Sept 2023
Nancy we are so happy to hear you enjoyed The Jolly Roger. We hope to have the opportunity to host you again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Jolly Roger Vacation

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!
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place

The house was amazing. The view is great, the place was really clean. The process was easy.
Stayed 3 nights in Mar 2024
Response from VrboOwner on 25 Mar 2024
Thanks, Helio. Please come back and stay with us again any time! Sean, iTrip Annapolis
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Family Getaway

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!
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Summer getaway

Great and very clean house with an outstanding deck over looking the Severn River
Stayed 3 nights in Jul 2023
Response from VrboOwner on 3 Aug 2023
Thank you Garrett for the kind review of The Jolly Roger. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Boatshow family gathering

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Pleasant stay

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.
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

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!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a view

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect saty for family reunion

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!
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

What a beautiful view of the river!

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic View

This home has a beautiful deck, with a fantastic water view. The house has a well equipped kitchen, and updated bathrooms.
Stayed 3 nights in Jul 2024
Response from VrboOwner on 16 Jul 2024
Thank you for staying with us Linda & for your kind feedback! We would be happy to host you again, Melissa~iTripAnnapolis
From a partner site

10/10 Excellent

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
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous views

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.
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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice Place Fantastic Sunset

House was very well equipped for all. Kids (toys) to adults (outdoor seating, dock , kayaks). Most definitely recommend for large gatherings
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

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.
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing waterfront view !

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
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
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Jolly Roger

Great!
Stayed 6 nights in Jul 2023
Response from VrboOwner on 4 Aug 2023
Thank you for your review of The Jolly Roger. Please come back and stay with us again. Safe Travels! -Tiffany
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful location for a tough trip

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!
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!
From a partner site

10/10 Excellent

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!
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
Verified review

6/10 Okay

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.
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Four couples long weekend

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!!
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion

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.
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

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.
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
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