Entire home

Waterfront dog-friendly Private Pier, Game Room, mins to Annapolis Jolly Roger

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Welcome to the Jolly Roger!
The view of the home as you walk up from the home's private pier
Gather around the big screen TV in the family room overlooking the deck.
Arriving by boat?  Walk up the stairs from the private pier to the gorgeous Jolly Roger!
The gourmet kitchen overlooks the dining room and has great views of the water.

Reviews

10 out of 10

Exceptional

4 bedrooms3 bathroomsSleeps 12223.0 sq m

Popular amenities

  • Kitchen
    Kitchen
  • Washer
    Washer
  • Dryer
    Dryer
  • Pet-friendly
    Pet-friendly
  • Free WiFi
    Free WiFi
  • Air conditioning
    Air conditioning

Explore the area

Map
Crownsville, MD
  • Westfield Annapolis Mall
    16 min drive
  • Annapolis Mall Shopping Center
    16 min drive
  • Maryland Renaissance Festival
    19 min drive
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    30 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
Porch or lanai
Kitchen
Balcony
Separate dining area
Garden
Dining Area

About this property

Waterfront dog-friendly Private Pier, Game Room, mins to Annapolis Jolly Roger

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.

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

Important information

You need to know

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

About the area

Crownsville

Located on the waterfront, this holiday home is in Arden-on-the-Severn, a neighbourhood in Crownsville. Maryland Hall for Creative Arts and Ballet Theater of Maryland are cultural highlights, and travellers looking to shop may want to visit Arundel Mills Mall and Westfield Annapolis Mall. Travelling with kids? Consider Annapolis Bowl and Crofton Bowl. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Crownsville, MD

What's nearby

  • Westfield Annapolis Mall - 16 min drive
  • Anne Arundel Medical Center - 17 min drive
  • Navy-Marine Corps Memorial Stadium - 20 min drive
  • U.S. Naval Academy - 21 min drive
  • Annapolis City Dock - 23 min drive

Getting around

  • Odenton Station - 20 min drive
  • Baltimore Washington International Airport (BWI) - 30 min drive

Restaurants

  • ‪Chick-fil-A - ‬18 min drive
  • ‪McDonald's - ‬18 min drive
  • ‪Starbucks - ‬18 min drive
  • ‪Big Bean - ‬19 min drive
  • ‪Mi Pueblo II - ‬18 min drive

Frequently asked questions

Is Waterfront dog-friendly Private Pier, Game Room, mins to Annapolis Jolly Roger pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Waterfront dog-friendly Private Pier, Game Room, mins to Annapolis Jolly Roger?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront dog-friendly Private Pier, Game Room, mins to Annapolis Jolly Roger?

Checkout is at 11:00 AM.

Where is Waterfront dog-friendly Private Pier, Game Room, mins to Annapolis Jolly Roger located?

Located on the waterfront, this family-friendly holiday home is within 9 mi (15 km) of Joyces Marina, Annapolis Bowl and Westfield Annapolis Mall. Annapolis Mall Shopping Center and Eisenhower Golf Course are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 30 out of 31 reviews" "
Rating 8 - Good. 1 out of 31 reviews" "
Rating 6 - Okay. 0 out of 31 reviews" "
Rating 4 - Poor. 0 out of 31 reviews" "
Rating 2 - Terrible. 0 out of 31 reviews" "

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Peter N.

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

10/10 Excellent

Camilla M.

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

10/10 Excellent

Linda H.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Jim C.

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

10/10 Excellent

A.J. S.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Angela w.

Delightful, picturesque home on the river.
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.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Sarah W.

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

10/10 Excellent

Alyssa A.

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

10/10 Excellent

Helio M.

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

10/10 Excellent

Suzanne H.

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

8/10 Good

Sil S.

Liked: Check-in, communication, location, listing accuracy
Snowed in
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, and we hoped for a response from the rental company. 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 just two hours longer. The experience was lovely, but the snow removal issue and the additional fee left us somewhat dissatisfied. Would definitely recommend staying here, just make sure there’s no snow in the forecast otherwise you will be left trying to figure out how to shovel it yourselves with no shovel available on the premises.
Stayed 2 nights in Jan 2024

10/10 Excellent

Walter G.

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

10/10 Excellent

Teresa S.

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

10/10 Excellent

Nancy R.

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

10/10 Excellent

Shankari S.

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

10/10 Excellent

Joe H., St. Petersburg

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

10/10 Excellent

Kevin G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jolly Roger
Great!
Stayed 6 nights in Jul 2023

10/10 Excellent

Garrett R.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kimberly G.

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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Kirra E.

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!

10/10 Excellent

Treva G.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Betty M.

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

10/10 Excellent

Maria B.

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

10/10 Excellent

Lucy A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Set your sails for the Jolly Roger!
Nothing could beat the spectacular view! The Navy and nautical themes fit the setting -- and our family -- perfectly. I've never stayed in a house so well appointed -- every bowl, mug, dishware and kitchenware you could possibly want. An entire downstairs fitted out for kids (and kids at heart). Excellent location with good restaurants nearby and easy accesss to Annapolis. It made for a very memorable vacation for our adult family, even more special for us since we landed here after having to "salvage" our original vacation at the very last minute.
Stayed 3 nights in Aug 2022

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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