Entire home

Captain's Quarters - Eastport!

Photo gallery for Captain's Quarters - Eastport!

Exterior
Dining
Room
Outdoor dining
Private kitchen

Reviews

9.4 out of 10

Exceptional

4 bedrooms3 bathroomsSleeps 1023540.6 sq ft

Popular amenities

  • Parking available
    Parking available
  • Pet-friendly
    Pet-friendly
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning
  • Barbecue grill
    Barbecue grill
  • Outdoor space
    Outdoor space

Explore the area

Map
Annapolis, MD
  • Annapolis City Dock
    20 min walk
  • Ego Alley
    3 min drive
  • Annapolis Maritime Museum
    3 min drive
  • Annapolis, MD (ANP-Lee)
    16 min drive

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Kitchen
Office
Garden
Dining Area

About this property

Captain's Quarters - Eastport!

Ditch the car, bring the family and the dog and make this beloved and restored 1920's bungalow in the desirable maritime neighborhood of Eastport yours for a weekend, a week or longer. Enjoy the best of Annapolis with an easy one mile walk to Downtown Annapolis, City Dock, Naval Academy, State House, etc.

The Captain’s Quarters is a unique mix of old and new craftmanship featuring wood floors (some that creak) covered in oriental rugs, wood furniture, and hand-picked antiques that all reflect Captain Paul’s style, adding up to good old fashioned homey and relaxed comfort for up to ten guests. The Captain's Quarters has four Queen bedrooms and a full Futon sofa, but we think the home is best arranged for a group of eight or fewer. Uniquely, the Captain’s Quarters provides both a primary and secondary suite with full ensuite bathrooms; perfect for two families or accommodating the In-Laws.

We pride ourselves in providing the best of green living with rooftop solar panels, permeable gravel driveway, energy efficient tankless water heater (NO Navy Showers!) composting, recycling, organic garden, fig & pawpaw trees, 2 fish ponds, and environmentally friendly landscaping. We offer a single off-street parking spot with only two steps up to enter a spacious foyer to unload and rest at the end of your day’s journey. There is also plenty of free, on-street parking for extra vehicles. Ceiling fans, central AC and a private, fenced backyard with patio and grill, chiminea, lawn furniture, and plenty of shade trees add up to the perfect place to relax and entertain.

The Captain’s Quarters provides complimentary wireless internet access, two smart TVs, coffee & tea with proper brewing devices, two office spaces with desks and chairs for your teleworking needs, a fitness nook in the master bedroom with weight bench and yoga mat, and numerous books to research sailing and the local area.

As mentioned above, most Annapolis destinations are within walking distance, however, if you want to experience travel the way the locals do - Eastport residents fully utilize the Water Taxi!

The Captain's Quarters is just a three minute walk to the water taxi pick up spot @ South Annapolis Yacht Center (750 Boucher Ave.). A beautiful and entertaining ride takes you directly to the Annapolis City Dock with a few other dockside (and potentially boat side) pickups along the way. Don't forget to ask your Captain for his or her recommendations and local info.

This is unique and exciting addition to your trip - a MUST on your to-do checklist!

Note: On occasion, a local service provider may enter the backyard shed he has rented for five years to store or retrieve tools. Visits are never after dark, rarely if ever on weekends, are usually very brief and guests will almost always be informed in advance. We thank you for your cooperation.

Property manager

Carolyn R. Leonforte Howard

Languages

English

Add dates for prices

Amenities

Kitchen
Pet-friendly
Free WiFi
Air conditioning
Outdoor space
Parking available

Similar properties

House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

Events allowed: family gatherings

Pets

Pets allowed: less than 23 kg per pet (limit one pet total)

Smoking

Smoking is not permitted
Check-in window: 4:00 PM
Checkout time: 11:00 AM
Quiet Hours: 10:00 PM- 10:00 AM

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
Parties and events (including family gatherings) are allowed on site. Maximum attendees: 20
Long-term renters welcome
This property uses solar energy, plus eco-friendly cleaning products
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
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Annapolis

Annapolis is home to this holiday home. Annapolis Maritime Museum and The Colonial Players are cultural highlights, and travellers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. French Soldiers Monument and Wild Bird Center are also worth visiting.
Map
Annapolis, MD

What's nearby

  • Annapolis City Dock - 20 min walk
  • U.S. Naval Academy - 3 min drive
  • Annapolis Maritime Museum - 3 min drive
  • Maryland State House - 3 min drive
  • Navy-Marine Corps Memorial Stadium - 5 min drive

Getting around

  • Odenton Station - 24 min drive
  • Fort Meade, MD (FME-Tipton) - 28 min drive

Restaurants

  • ‪The Choptank - ‬18 min walk
  • ‪Starbucks - ‬2 min drive
  • ‪O'Brien's Annapolis' Original Steakhouse - ‬20 min walk
  • ‪Chick & Ruth's Delly - ‬3 min drive
  • ‪Chipotle Mexican Grill - ‬20 min walk

Frequently asked questions

Is Captain's Quarters - Eastport! pet-friendly?

Yes, this property allows pets (limit 1 total) with a maximum weight of up to 23 kg per pet.

What time is check-in at Captain's Quarters - Eastport!?

Check-in begins at 4:00 PM.

What time is check-out at Captain's Quarters - Eastport!?

Checkout is at 11:00 AM.

Where is Captain's Quarters - Eastport! located?

Situated in Annapolis, this holiday home is steps from Spa Creek and 1.3 mi (2.1 km) from U.S. Naval Academy. Kunta Kinte Plaque & Alex Haley Memorial and Maynard-Burgess House are also within 1 mile (2 km).

Reviews

9.4

Exceptional

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

8.8/10

Cleanliness

9.2/10

Check-in

9.2/10

Communication

9.6/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Brittany D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing customer service!
Cute little property with lots of character and huge master bedroom was great for my little one. They even had 2 rocking chairs which was super helpful at night. Very responsive team too! We needed to check in a few hours earlier for my little one and they were very sweet in letting us do so. Overall highly recommend!
Stayed 2 nights in Oct 2024

8/10 Good

Verified traveller

Liked: Check-in, location, listing accuracy
Needs work
The house might needs a lit bit of work to modernization. There was no phone to directly reach out to the manager. Besides that, I appreciate the response about the loose faucet. Thanks
Stayed 2 nights in Aug 2024

10/10 Excellent

Heidi R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Comfortable and easy
The place was comfortable, felt like we were staying at our grandmas house. Cute neighborhood, walkable. Beds were comfy. Used for a small work retreat and was great for 5 women!
Stayed 2 nights in Jun 2024

10/10 Excellent

Abigail H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Eastport Convenience!
This is our second time staying at this property for the Helly Hansen Sailing Regatta. Its conveniently located near where we keep the boat for this weekend (EYC). Property is a little quirky in a great way. Very easy check-in with the electronic lock. Host was great- offered to bring us coffee when they realized they had forgotten to supply. Very spacious backyard! Can't wait to return next year!
Stayed 4 nights in May 2024
This review comes from a trusted partner site and has not been verified.

8/10 Good

Inna P.

Short stay in Annapolis with family and friends
We loved the location and neighborhood, the house was lovey too, the management team was also very helpful and responsive ( we had some glitches with electronic key access) . The reason for 4 star is beds-very uncomfortable mattresses ( soft, not enough support for 2 people in double beds) . Other than that, everything was great.

10/10 Excellent

Johnny J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Holiday Getaway
My family and I enjoyed our stay at Captain's Quarters in Annapolis. It was a convenient and spacious location for us (5 adults, 1 8 year old). We really appreciated the bedroom for grandma on the first floor. (We'd recommend a railing of some sort for the front porch.) The master bedroom was spacious and had a great tub! The host/management team was very friendly and extremely responsive, and we really appreciate that! Thank you for a great holiday stay!
Stayed 6 nights in Dec 2023

About the host

Hosted by Carolyn R. Leonforte Howard

Host profile image
Carolyn Leonforte Howard has traveled the globe for twenty years on Active Duty with the United States Air Force. She immersed herself in varying hospitality traditions and drank in the cultural differences surrounding travel in all nations. Her unique perspective translated to immediate success when she started her own STR journey upon receiving orders to Ramstein, Germany.

Carolyn developed strategies for success over her three and a half years overseas and was able to manage highly successful rentals, even with a six-hour time difference. Upon return, the hallmark of her plan was obvious, nothing had changed! The management strategy she worked so hard to perfect was so succinct there was no further daily interaction needed. As Carolyn brought two additional STRs online, she found herself asking why more people have not jumped at the opportunity to start their own holiday rentals for vacation travelers?

This is where B4K was born. It’s not easy for everyone to take the leap. Some have too much on their plates, some just don’t know where to start, and others have it all figured out but no longer wish to self-manage their properties. B4K offers a perfect balance for achieving passive income through STRs. Using a combination of tried-and-true strategies, as well as thorough data analysis, Carolyn’s goal is to provide immediate peace of mind for her clients as she helps them build their own success story.

Carolyn has a 4.9 Star Rating over six years on competitive platforms and has copied all listings to Vrbo!

Why they chose this property

From the homeowner, Captain Paul: "Deep backyards with ld and tall trees. Every street is different. I can walk to restaurants, marinas, convenience stores, post office, athletic club, bakery, gourmet to go and a package store! Water taxi stop nearby. Oh and the backyard! Private, completely fenced in (let the children and doggie run around), enjoy the Black Walnut, Crepe Myrtle, Hibiscuses, Mock Orange, Spirea and Bridal Bouquets, patio and fish ponds--and grill with plenty of metal and wood furniture and two tables with umbrellas."

What makes this property unique

Captain Paul's unique description: "Unique is the word. PLEASE stay here if you like the unusual, the distinct and the slightly quirky. My home is perfect for you if you crave light and airy, unique and eclectic, wood floors and oriental rugs, solid wood furniture and floors.If you are looking for the standard, the average, the normal this may not be the best choice for you.. But here you will have the comfort of knowing that your host cares about you and has loved his home for more than 30 years, that the neighbors are nice (next door-a retired Navy Admiral on one side and a veteran Marine Major). Please understand that I am doing my best so that you can enjoy my simple and comfy home that had been my residence for many years. I provide coffee and a wide selection of tea, condiments and spices in a well equipped kitchen with gas cooking--and all the while your electricity is being delivered by rooftop solar panels, and a highly efficient tankless water heater that delivers all you need for a house full of guests."

Languages:

English
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