Ahoy! Game Room, Screened Porch, Yard Mins to DTA

Annapolis, Maryland
$603 avg/night Minimum Stay 2 Nights
Bed 3

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 9

Max Sleeps

Night 2 nights

Min Stay

Experience the Difference: Professionally Managed by iTrip Annapolis

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 withQueen 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.

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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

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* 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

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    3 Bedrooms Sofa Bed
  • GENERAL

    Recycling Unit Size: 1272 Sq Ft (118 Sq M) Uses Some LED Lighting
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Gas Grill Patio
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Shampoo
  • LANGS SPOKEN

    English
  • ENTERTAINMENT

    DVD Player Foosball Table TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Games
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 9

Map Map

School District Availability

Review Review

  • Mackenzie Q.

    Submitted Jul 16, 2025

    Stayed Jun 19, 2025

    A beautiful and spacious place that is so well decorated! Annapolis is an incredible town :)

  • Debra W.

    Submitted Apr 4, 2025

    Stayed Mar 30, 2025

    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.

  • Dina C.

    Submitted Mar 16, 2025

    Stayed Mar 12, 2025

    Enjoyable stay & quick proximity to USNA.

  • William C.

    Submitted Dec 16, 2024

    Stayed Dec 13, 2024

    We loved The Buccanneer. We were only in town for a quick weekend visit for the Army-Navy game and did not get a chance to spend much time at the house, but when we did we found it to be clean, comfortable, and convenient to town.

  • Brenna J.

    Submitted Nov 25, 2024

    Stayed Nov 15, 2024

    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.

  • Whitney W.

    Submitted Oct 19, 2024

    Stayed Oct 11, 2024

    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.

  • Rosemary H.

    Submitted Sep 10, 2024

    Stayed Sep 6, 2024

    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!

  • Margaret H.

    Submitted Aug 7, 2024

    Stayed Aug 1, 2024

    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.

  • Linda M.

    Submitted Aug 2, 2024

    Stayed Jul 26, 2024

    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.

  • Nicole H.

    Submitted Jul 29, 2024

    Stayed Jul 21, 2024

    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!

  • Sandra M.

    Submitted Jul 21, 2024

    Stayed Jul 19, 2024

    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!

  • Dennis K.

    Submitted Jul 6, 2024

    Stayed Jun 27, 2024

    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!

  • Dean D.

    Submitted Jul 1, 2024

    Stayed Jun 23, 2024

    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!

  • Kelly S.

    Submitted Jun 23, 2024

    Stayed Jun 19, 2024

    We were very pleased with our stay and would stay here again.

  • Ronald V.

    Submitted Jun 21, 2024

    Stayed Jun 9, 2024

    It’s an amazing house, near everything . Everything you need is available at the property We had a great time

  • Missy F.

    Submitted Jun 3, 2024

    Stayed May 21, 2024

    This is a great house with amazing outdoor space

Your dates are Available!

Total

Includes taxes and fees
$603+
View details