Entire home·Private host

Captain's Quarters - Eastport!

Holiday home with kitchen, near U.S. Naval Academy

Photo gallery for Captain's Quarters - Eastport!

Fridge, microwave, oven, stovetop - Captain's Quarters - Eastport! (Annapolis)
Marina - Captain's Quarters - Eastport! (Annapolis)
Interior - Captain's Quarters - Eastport! (Annapolis)
TV, offices - Captain's Quarters - Eastport! (Annapolis)
4 bedrooms, iron/ironing board, WiFi, bed sheets - Captain's Quarters - Eastport! (Annapolis)
Captain's Quarters - Eastport! provides amenities, such as a garden and laundry facilities. Stay connected with in-room WiFi.

Reviews

9.2 out of 10
Wonderful

Entire home

4 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Kitchen
  • Pet-friendly
  • Air-conditioning
  • Laundry room
  • Outdoor space
  • Barbecue grill

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.

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 amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Hair dryer
  • Shower

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • Up to 23 kg per pet

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

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)
  • First aid kit
  • Fire extinguisher

General

  • At least 80% lighting from LEDs
  • Composting
  • Eco-friendly cleaning products used
  • Garden
  • Recycling
  • Solar energy

Similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Rules

Check-in window: 4:00 PM Checkout time: 11:00 AM Quiet Hours: 10:00 PM- 10:00 AM No commercial photography and filming allowed Number of guests: 8...

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 23 kg per pet)
Note from host: Charge may apply

Children and extra beds

Children are welcome

Events

Events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 are allowed on site
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
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

Property is also known as

67ffdf0e02fdee001328961a

About the area

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. Visit our Annapolis travel guide
View more Holiday homes in Annapolis
Map
Annapolis, MD

What's nearby

  • U.S. Naval Academy
    U.S. Naval Academy
    4 min drive - 2.1 km
  • Chesapeake Bay Bridge
    Chesapeake Bay Bridge
    19 min drive - 18.0 km
  • Annapolis Maritime Museum
    19 min walk - 1.6 km
  • Annapolis City Dock
    20 min walk - 1.7 km
  • Westfield Annapolis Mall
    11 min drive - 8.3 km

Getting around

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

Restaurants

  • The Choptank
  • Starbucks
  • Carrol's Creek Cafe
  • Boatyard Bar & Grill
  • O'Brien's Oyster Bar & Seafood Tavern

Frequently asked questions

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

Yes, this property allows dogs (limit 2 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. Annapolis Harbor and Kunta Kinte Plaque & Alex Haley Memorial are also within 1 mile (2 km).

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Captain's Quarters - Eastport! Reviews

Reviews

Wonderful

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.
More informationOpens in a new window
Rating 10 - Excellent. 5 out of 9 reviews
Rating 8 - Good. 4 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.0

Cleanliness

9.8

Location

Reviews

Verified

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
Verified

8/10 Good

Martha J.

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

Comfortable, clean ,convenient

Nice place but dated if that matters. Clean, comfortable, host was very helpful. Convenient to downtown. We also went to close by Sandy point to see the Lights on the bay. We reccomend a better door offering more privacy in downsatairs bath.
Stayed 3 nights in Dec 2024
Verified

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
Verified

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
Verified

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
From a partner site

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.
Verified

8/10 Good

Robert M.

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

Commissioning week 2025

Over all the property met our needs. It is a great location. Downtown and the Naval Academy are within walking distance. The house could use some updating but was comfortable. The neighborhood is quiet and feels safe.
Stayed 7 nights in May 2025
Verified

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
Verified

10/10 Excellent

Tom S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 6 nights in Aug 2025