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Available for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room

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Ahoy and welcome to The Buccaneer's spacious 4 seasons room overlooking the private backyard.
Relax in the family room on the main floor.
There is a bedroom and full bathroom on the main level of the home and 2 more bedrooms and another full bath upstairs.
The spacious yard and playset are perfect for the younger family members and dogs!
The kitchen is conveniently located in the middle of the home.

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 9

Popular amenities

  • Barbecue grill
  • Washer
  • Dryer
  • Kitchen
  • Pet-friendly
  • Parking available

Explore the area

Map
Annapolis, MD
  • Maryland Quiet Waters Park
    ‪5 min drive‬
  • Annapolis City Dock
    ‪7 min drive‬
  • U.S. Naval Academy
    ‪9 min drive‬
  • Annapolis, MD (ANP-Lee)
    ‪15 min drive‬

Rooms & beds

3 bedrooms (sleeps 9)

Family Room

1 Double Sofa Bed

Main Floor Bedroom

1 Queen Bed

Upstairs Bunk Room

1 Single Bunk Bed

Upstairs King

1 King Bed

2 bathrooms

Main Floor

Bathtub or shower · Toilet

Upstairs Hall Bath

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden
Dining area

About this property

Available for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room

Still available for Commissioning Week 2025!

Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. This charming and fun home has a four-season patio, with adjustable plexiglass windows, overlooking the fenced-in backyard and full entertainment room in the basement, complete with foosball, an arcade and a theater room.

This home's full kitchen, dining area, family room, bedroom with Queen bed and full bath are on the main floor. The kitchen is fully-stocked with cookware, stainless steel appliances and a chef's butcher block built into the countertop. The custom dining room table is built in to allow up to 8 guests to gather and enjoy a family meal. Head out to the 4-seasons room/screened-in porch and private backyard.

The 2nd bedroom, located upstairs, has a bunk bed with a Full bed over 2 Twin beds. The 3rd bedroom, also located on the 2nd floor, has a King bed.

The home is just a short walk through a quiet neighborhood to Capital SUP on Back Creek, where paddle boards and kayaks are available for rent. Looking for a fun adventure on the water? You will be conveniently located within walking distance to Ellen Moyer Park, Annapolis Maritime Museum and Bert Jabin Yacht Yard. Or, take a water taxi into Annapolis! Just 2 blocks away at the waterfront of King James Landing, you can hire a water taxi.

SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 9:
Main Floor Bedroom:
-Queen Bed
-Full bathroom in the hall with shower/bath combo

King Bedroom
-2nd Floor
-Full bath in the hall with shower/bath combo

Upstairs family guest room
-Full bed over Two Twins bunk bed
-Full bath in the hall with shower/bath combo

Family Room
Queen sleeper sofa

HIGHLIGHTS:
-Large screened-in patio overlooking the big private backyard
-Built-in kitchen dining table seats 6-8
-High Speed Internet and WiFi
-Coffee maker with starter pack of coffee/creamers
-BBQ gas grill (propane included)
-Luxury bed and bath linens, complimentary toiletries Starter Kit, and boutique-level service
-Parking for 2-3 cars in driveway
-Full-sized washer & dryer
-Private fenced-in backyard
-Dogs allowed with $150 non-refundable fee paid prior to checkin
-Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions.
***************
Property Distance to:
-Downtown Annapolis – 2.5 miles (10 mins)
-U.S. Naval Academy – 3 miles (10 mins)
-Washington, DC – 33 miles
-Baltimore - 34 miles
***************
* Amenity pack with starter coffees, sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going
* All beds are made for you with freshly-laundered sheets & towels in the baths.

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. Please respect the neighbors and neighborhood. No parties. Quiet neighborhood hours are 9pm-8am!
Check-in time: 4:00 pm
Check-out time: 11:00 am

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

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House Rules

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

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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

Annapolis

Annapolis is home to this holiday home. Historical Society of Talbot County and Kunta Kinte Plaque & Alex Haley Memorial are local landmarks, and travellers looking to shop may want to visit Bay Bridge Market Place Shopping Center and Annapolis City Dock. Travelling with kids? Consider Wild Bird Center and Annapolis Maritime Museum. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Annapolis, MD

What's nearby

  • Maryland Quiet Waters Park - 5 min drive - 3.3 km
  • Annapolis City Dock - 7 min drive - 5.3 km
  • Annapolis Maritime Museum - 8 min drive - 5.1 km
  • Navy-Marine Corps Memorial Stadium - 9 min drive - 7.0 km
  • U.S. Naval Academy - 9 min drive - 6.3 km

Getting around

  • Odenton Station - 24 min drive
  • Fort Meade, MD (FME-Tipton) - 29 min drive

Restaurants

  • ‪McDonald's - ‬20 min walk
  • ‪The Choptank - ‬7 min drive
  • ‪Boatyard Bar & Grill - ‬7 min drive
  • ‪Pusser's Caribbean Grille - ‬7 min drive
  • ‪Carrol's Creek Cafe - ‬7 min drive

Frequently asked questions

Is Available for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Available for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room?

Check-in begins at 4:00 PM.

What time is check-out at Available for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room?

Checkout is at 11:00 AM.

Where is Available for CW 2025 Ahoy! The Buccaneer with 3-seasons room, fenced-in yard and rec room located?

This family-friendly Annapolis holiday home is within 1 mi (2 km) of Sparrows Beach, Bay Bridge Market Place Shopping Center and Annapolis Sailing School. Maryland Quiet Waters Park and Historic Mount Moriah AME Church are also within 2 miles (3 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. 13 out of 15 reviews
Rating 8 - Good. 2 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Dina C.

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

Buccaneer Review

Enjoyable stay & quick proximity to USNA.
Stayed 4 nights in Mar 2025

10/10 Excellent

Kelly S.

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

Adorable Home Perfect for Families

We were very pleased with our stay and would stay here again.
Stayed 4 nights in Jun 2024

10/10 Excellent

Debra W.

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

Family Trip

I have to say that my family and I had a wonderful stay at this house. It was a perfect location to visit both Washington DC and Annapolis. The house is in a quiet neighborhood with a great fenced in yard for small children or “canine children“. The theater room and game area were just the right space for my sons to have their own area of the house.My personal favorite spot was the enclosed back porch. With the table, seating and tv it was the perfect spot to relax on a warm evening.This home would definitely be at the top of my list if I were to visit the area again.
Stayed 4 nights in Mar 2025

8/10 Good

Whitney W.

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

Family Vacay

Overall the house was very accommodating and spacious! The highlights were the theater downstairs, the back patio, and bunk beds! It was in a great location for easy access to downtown Annapolis and food/shopping. The place had plenty of towels and kitchen items.
Stayed 5 nights in Oct 2024

10/10 Excellent

Ronald V.

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

Wonderful Property

It’s an amazing house, near everything . Everything you need is available at the property We had a great time
Stayed 4 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Katie C.

Great trip!

We have loved exploring Annapolis and DC with our family. The house has all the things we need and the added bonus of being kid friendly! We are loving it, thank you!
Stayed 4 nights in Mar 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Linda M.

The Buccaneer

We thoroughly enjoyed our stay at The Buccaneer! All rooms were very comfortable, great location, and very clean. We especially enjoyed the screened in porch - spent a lot of time there. Very easy access to Eastport and Main Street Annapolis. Our family birthday celebration was very special and successful.
Stayed 4 nights in Jul 2024

10/10 Excellent

Rosemary H.

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

Great Annapolis Visit

We really enjoyed our weekend in Annapolis and staying at the Buccaneer. The home was very comfortably furnished and fully equipped. We especially enjoyed the porch and the basement game and TV room. The kitchen was well stocked with good quality cookware and I was able to prepare the meals as planned. The beds were comfortable and the plush towels were great too. Our grandchildren have already asked to return next year!
Stayed 3 nights in Sep 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Brenna J.

Perfect Place

We stayed at The Buccaneer for our 20 year USNA reunion. Nestled in a cute neighborhood just 10 minutes from downtown Annapolis. Awesome, spacious screened in porch w a beautiful dining size table, great backyard, and just the right amount of space for two families of 5 w young kiddos. Linens were beautiful and stocked w plenty of towels, spotlessly clean, a great kitchen w all the amenities, and a beautiful finished basement w a movie room (perfect for the kids to disappear into). Beds were comfortable and more than enough storage space. Place was perfect and we would stay again.
Stayed 2 nights in Nov 2024

10/10 Excellent

Missy F.

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

great

This is a great house with amazing outdoor space
Stayed 4 nights in May 2024

8/10 Good

Margaret H.

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

Family vacation friendly

Great house in a great location. My kids (12 and 14 years old) enjoyed the theatre room and foosball table in the basement. I appreciated the newer appliances in the kitchen. Comfy seating in the kitchen and living room. Nice sized backyard with playset and outdoor games.
Stayed 4 nights in Aug 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Nicole H.

12 Pirates!

We loved the Pirate theme in this house! It was the perfect place for our families to relax after sailing the day away. Movie theater in the basement complete w popcorn machine, huge screened in porch and a playground out back. It’s a cozy house with comfy beds and everything we needed! We will definitely come back here!
Stayed 5 nights in Jul 2024

10/10 Excellent

Sandra M.

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

Wonderful Property!

We were in town for husband/father's funeral. The house was perfect for our stay. The kids loved the home theater soace and games in the basement. After a very long and difficult day, we were able to relax. They owners supplied all towels, linens and small bags of toiletries for our stay. The porch was large and peaceful. The kitchen was stocked well with all needed dishes, utensils, and pots and pans. If we need to stay in the area again, I would definitely choose this property!
Stayed 2 nights in Jul 2024

10/10 Excellent

Dennis K.

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

Annapolis, DC and Ocean City!

We had a great time and enjoyed the home. The kids loved the arcade game, foosball, and movie theater. My 78 yo dad had his own bath and a first floor bedroom. Everything was perfect. A few minor things but nothing even worth mentioning. Everyone was more than satisfied! Would stay here again o. A heartbeat!
Stayed 5 nights in Jun 2024

10/10 Excellent

Dean D.

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

Awesome in Annapolis

It is safe to say we scored when we booked the Buccaneer! The home was perfect. It was spacious enough for a few old friends and their boys to hang and reminisce. It was clean, in a great location and roomy. Despite our stay being in the middle of a heat wave we enjoyed the back patio. Speaking of a heat wave, when we arrived it was quite warm inside and we could not get the AC to stay set to a cooler temp. Melissa and her team were awesome when I brought this to their attention and worked with me until 11 PM to get the temp dropping! Who does that? We enjoyed our stay thoroughly and when back in Annapolis we will look to book the Buccaneer first!
Stayed 3 nights in Jun 2024

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests