Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

Photo gallery for Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

A white door with a glass panel and a black handle.
A kitchen with wooden cabinets, a granite countertop, and a built-in microwave.
A playground with a blue slide and climbing structure, surrounded by a sandy area and a white fence.
A bathroom with a shower, a toilet, and a sink.
A modern living room with a dark blue sofa, a round coffee table, and a wooden sideboard.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • At the center of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Close to Chesapeake Bay

Popular amenities

  • Toys
  • Barbecue grill
  • Air conditioning
  • Refrigerator
  • Onsite parking available
  • Washer

Explore the area

View in a map
Annapolis, MD
  • Place, Northern Chesapeake Bay
    ‪1 min walk‬
  • Place, U.S. Naval Academy
    ‪15 min drive‬
  • Place, Annapolis City Dock
    ‪16 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪48 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Double Bed

1 bathroom

Bathroom

Toilet · Shower only

Spaces

Kitchen
Outdoor play area
Garden
Dining area

Add dates for prices

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About the neighborhood

Annapolis

Located near the beach, this vacation home is in Oyster Harbor, a neighborhood in Annapolis. John Smith House and William Paca House are local landmarks, and travelers looking to shop may want to visit Annapolis City Dock and Bay Bridge Market Place Shopping Center. Wild Bird Center and Annapolis Maritime Museum are also worth visiting. Jet skiing, kayaking, and water skiing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
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Map
Annapolis, MD

What's nearby

  • Northern Chesapeake Bay - 1 min walk - 0.1 km
  • U.S. Naval Academy - 15 min drive - 8.2 km
  • Annapolis City Dock - 16 min drive - 8.9 km
  • Navy-Marine Corps Memorial Stadium - 17 min drive - 10.7 km
  • Chesapeake Bay Bridge - 31 min drive - 24.8 km

Getting around

  • Odenton Station - 29 min drive
  • Fort Meade, MD (FME-Tipton) - 31 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪The Beacon Restaurant - ‬8 min drive
  • ‪Royal Farms - ‬8 min drive
  • ‪Grump's Cafe - ‬5 min drive
  • ‪Jack's Fortune - ‬5 min drive

Frequently asked questions

Is Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis ?

As of Nov 6, 2026, prices found for a 1-night stay for 2 adults at Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis on Nov 30, 2026 start from $424, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis ?

Check-in begins at 4:00 PM.

What time is check-out at Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis ?

Check-out is at 10:30 AM.

Where is Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis located?

Located in Oyster Harbor, this vacation home is steps from Chesapeake Bay and Northern Chesapeake Bay. Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park are also within 3 mi (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 99 out of 100 reviews
Rating 8 - Good. 0 out of 100 reviews
Rating 6 - Okay. 0 out of 100 reviews
Rating 4 - Poor. 0 out of 100 reviews
Rating 2 - Terrible. 1 out of 100 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy two bedroom, the development has a private beach quiet neighborhood… nice stay
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

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

Great weekend getaway!

Great property and great time in Oyster Harbour!
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

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

Wonderful location

The hosts were so attentive and friendly, the location is wonderful- close to downtown yet tucked away in a nice neighborhood away from everything! Perfect getaway, can’t wait to rent this home again in the future.
Stayed 5 nights in Jun 2024
Verified review

10/10 Excellent

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

Clean & cozy

Great location, clean and cozy.
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

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

Wonderful VRBO

Quiet neighborhood, beautiful home
Stayed 5 nights in Apr 2023
Verified review

10/10 Excellent

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

Great stay!

Oyster Harbor is a wonderful home to stay when in Annapolis. The cottage has everything you need to feel comfortable, make a meal, walk the lovely neighborhood and have easy access to DTA. We are lucky to have found this gem and are sure to return.
Stayed 2 nights in Mar 2023
Verified review

10/10 Excellent

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

Beautiful place

Wonderful
Stayed 4 nights in Sep 2023
Verified review

10/10 Excellent

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

Tranquility and comfort

Nicely equipped, very comfortable and lovely location.
Stayed 6 nights in Jun 2023
Verified review

10/10 Excellent

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

Easy trip for visiting family and Annapolis

Fantastic location - was close enough to downtown Annapolis for easy access but also felt like a beach getaway being just a short the the community beach. Incredibly responsive hosts!
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

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

Great Stay

We loved the community/neighborhood. It was perfect for walks and the beach area was excellent and very well kept. The house was perfect; everything you needed and then some. We felt very comfortable and enjoyed the stay! Would definitely book this property again.
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
"Remarkable! To sum it up, my two young children and I had an unforgettable stay. Winston and Carolyn were truly the hosts of all hosts—there aren’t enough stars to give or words to describe how wonderful it was."."
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
The property was quaint and nicely appointed. Comfortable and clean. Hosts were wonderful!
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Enough space for us; very close to the water and also super clean and well kept. Would definitely return.
Stayed 2 nights in Sep 2022
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
The cottage was wonderful - clean, quiet, and just great. Fit all of our needs. Winston and Carolyn were absolutely fantastic and I look forward to staying again on my next trip to Annapolis. I highly recommend this great place in such a quiet, charming, and safe neighborhood.
Stayed 3 nights in Jul 2022
Verified review

10/10 Excellent

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

Oyster Harbor Cottage

We stayed for 4 days and loved it. The cottage was tastefully done and immaculate! A short 5 walk to a private beach was a wonderful bonus. The beds were very comfortable and our hosts Winston and Carolyn were so accommodating. We would definitely go back!
Stayed 4 nights in Oct 2023
Verified review

10/10 Excellent

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

Weekend with grandson

A great location for our weekend in Annapolis with our 6 year-old grandson. Having the beach and playground just down the street was perfect! Clean house. Great local host!
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

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

Perfect spot for a relaxing getaway

We stayed here last year for a long weekend and loved it so much we came back for a full week this year! It's the perfect place to relax and de-stress -- quiet neighborhood, beautiful beach, comfortable house, wonderful hosts. We spent all day on the beach with our 4-year-old and enjoyed trying different local restaurants -- recommended by Winston and Carolyn -- in the evenings. This is a dream spot -- we will be back again!
Stayed 6 nights in May 2022
Response from VrboOwner on May 27, 2022
Jennifer and Brock it was great to see you all again. Thank you again for choosing to come back for a longer stay. We look forward to seeing you again soon. Enjoy the summer and stay well. Winston & Carolyn
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
The Anchors is a wonderful place in every way. The house is beautifully furnished, spotless, has every amenities you could every need and is in one of the best locations in Annapolis. The house is located in a quiet neighborhood surrounded by water Yet a short distance from downtown. The owners are incredibly hospitable and had great communication. Definitely a wonderful place to stay!
Stayed 2 nights in Sep 2022
Verified review

10/10 Excellent

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

Awesome cottage for Annapolis events

The Host was accommodating and easy to deal with on every way. The property easily accommodated 2 couples and literally is just a few steps from the local beach in a quaint and quiet neighborhood. Also an easy 5-10 minute drive to all local events and experiences around downtown Annapolis and the Naval Academy.
Stayed 4 nights in Feb 2023
Verified review

10/10 Excellent

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

Perfect Stay

My husband, my son and I loved the or petty. It was extremely clean and had everything we needed. The are is calm so you have a great night sleep. The owners are very nice and welcoming. Could not ask fir a better stay, it is 15 minutes away from the historic district.
Stayed 3 nights in Mar 2021
Verified review

10/10 Excellent

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

Amazing house!!!

We had an absolutely wonderful stay! The house was immaculate and had everything we needed! Winston and Carolyn were very responsive from the moment we booked the property. We couldn’t have asked for a better experience. We can’t wait to book this property again!
Stayed 4 nights in Aug 2019
Response from VrboOwner on Mar 29, 2020
So glad it worked out for you all. We look forward to seeing you again soon. Winston and Carolyn
Verified review

10/10 Excellent

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

Best Place to Stay!

We have stayed at The Anchors several times when visiting Annapolis and hope you will as well. The home is beautifully and comfortably furnished with all you need. The location is ideal, close to downtown in a beautiful water community ideal for long walks. The hosts are welcoming and really interested in your comfort. We will be back for sure!
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

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

Perfect

I would definitely recommend this cottage! I was very impressed with cleanliness of this home. The neighborhood is very quiet and friendly. We booked this home to attend my son’s graduation from the US Naval Academy. It was the perfect distance from the stadium. The beach was very relaxing and private. We hated to leave.
Stayed 6 nights in May 2025
Verified review

10/10 Excellent

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

Peaceful and Easy

Clean, well stocked, nice furniture, quiet neighborhood, lots of amenities, good location. I would highly recommend this property. We stayed very comfortably for a week. Went in and out of DC without issue. Check in and out was easy. I'd stay here again.
Stayed 6 nights in Jul 2024
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