How much is parking at 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free?

On-site parking is available at the property.

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free Reviews, Deals & Photos 2026

Q: Is 2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free pet-friendly?

Yes, pets are allowed at this property.

Q: 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 Eisenhower Golf Course, Annapolis Bowl and Westfield Annapolis Mall. Annapolis Mall Shopping Center and B&A Trail are also within 9 miles (15 km).

10/10 Excellent

Lydia W.

8 Oct 2025

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

Incredible view! We had a great time

Stayed 2 nights in Oct 2025

10/10 Excellent

Nancy R.

6 Sept 2023

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

Helio M.

17 Mar 2024

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

Peter N.

9 Oct 2024

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

Shankari S.

28 Aug 2023

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

Camilla M.

20 Aug 2024

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.

8 Jul 2024

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.

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

Stayed 3 nights in Jun 2024

10/10 Excellent

Alyssa A.

26 Mar 2024

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

Walter G.

24 Nov 2023

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

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

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!

Stayed 3 nights in Apr 2024

10/10 Excellent

Suzanne H.

11 Mar 2024

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

10/10 Excellent

A.J. S.

5 Jun 2024

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

10/10 Excellent

Teresa S.

26 Oct 2023

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

8/10 Good

Sil S.

22 Jan 2024

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

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

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.

10/10 Excellent

Joe H., St. Petersburg

13 Aug 2023

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

Treva G.

27 Jun 2023

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

Garrett R.

19 Jul 2023

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

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!

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.

Stayed 3 nights in Apr 2025

10/10 Excellent

Maria B.

22 Sept 2022

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

Verified traveller

28 Nov 2022

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

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

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.

Stayed 6 nights in Jun 2023

10/10 Excellent

Betty M.

17 Oct 2022

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

2026 Commissioning Week Promo: Book 6 Nights, Get the 7th Free

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