Consider a stay at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free and take advantage of a firepit, a garden and laundry facilities. Guests can connect to free in-room WiFi.
Reviews
9.89.8 out of 10
Exceptional
Entire home
4 bedrooms3 bathroomsSleeps 12223 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Add dates for prices
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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.
Property amenities
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Ice maker
Kitchen island
Microwave
Oven
Paper towels
Refrigerator
Toaster
Dining
Dining table
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
3 bathrooms
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided
Living spaces
Dining table
Living room
Entertainment
Books
DVD player
Games
Smart TV with cable/satellite channels
Outdoor areas
Balcony
Firepit
Garden
Gas grill
Outdoor furniture
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
On the waterfront
Things to do
Foosball table
Kayak
Table tennis
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events 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
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
About the area
Located on the waterfront, this holiday home is in Arden-on-the-Severn, a neighbourhood in Crownsville. Ballet Theater of Maryland and Annapolis Civil Rights Plaque 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. Visit our Crownsville travel guide
Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?
Yes, pets are allowed at this property.
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).
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2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
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!
This home has a beautiful deck, with a fantastic water view. The house has a well equipped kitchen, and updated bathrooms.
Linda H.
Stayed 3 nights in Jul 2024
From a partner site
10/10 Excellent
Jim C.
5 July 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
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.
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
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!
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!
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.
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.
Sil S.
Stayed 2 nights in Jan 2024
From a partner site
10/10 Excellent
Angela w.
31 May 2024
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.
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!
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!
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.
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
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.
Mary Kate H.
Stayed 3 nights in Apr 2025
From a partner site
10/10 Excellent
Kimberly G.
13 July 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.
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