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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

Newly decorated living space
Newly added porch
Private kitchen
Private kitchen
Private kitchen

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Barbecue grill
  • Garden

Explore the area

View in a map
Annapolis, MD
  • Place, Maryland Quiet Waters Park
    ‪4 min drive‬
  • Place, Bay Bridge Market Place Shopping Center
    ‪5 min drive‬
  • Place, Bay Ridge Beach
    ‪8 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪47 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

About this property

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

New Outdoor Space for 2026! Enjoy sunrises on the newly built porch. A great space for morning coffee or to spend an evening outdoors. This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay. Whether you're looking for a place to relax and recharge or to enjoy water sports, this is the place for you. Just a 5 minute stroll and you’re on the beach or curl up and enjoy the cozy interior of this home. Kitchen has everything you need to prepare meals or store leftovers from one of many nearby restaurants. Located on the shores of the Chesapeake Bay, this property is only 5 miles from downtown historical Annapolis and 35 minutes from Washington DC. Just the spot for a relaxing getaway on your own or a fun packed time with family and friends. This community offers a variety of activities from water sports to beach volleyball. Want to keep up with your exercise routine, try our 1 mile, three station exercise circuit course. Want to take your canoe/kayak out, you have access to the water at the boat ramp just a short walk away. A kid and pet friendly neighborhood with playgrounds and doggie stations nearby for your usage. Check out the video for more information about the neighborhood. Welcome home to "The Anchors"!
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:30 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
Please do rearrange any furniture.
To avoid additional fees, do not allow additional guest to stay overnight.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

About the neighborhood

Annapolis

Located near the beach, this vacation home is in Oyster Harbor, a neighborhood in Annapolis. Historical Society of Talbot County and Kunta Kinte Plaque & Alex Haley Memorial are local landmarks, and travelers looking to shop may want to visit Bay Bridge Market Place Shopping Center and Annapolis City Dock. 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

  • Maryland Quiet Waters Park - 4 min drive - 4.2 km
  • Bay Bridge Market Place Shopping Center - 5 min drive - 4.2 km
  • Historical Society of Talbot County - 7 min drive - 4.8 km
  • Bay Ridge Beach - 8 min drive - 6.9 km
  • Carrs Beach - 9 min drive - 6.9 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Sammy's Italian Pizza Kitchen - ‬8 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Royal Farms - ‬8 min drive
  • ‪Eastport Kitchen - ‬8 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 May 6, 2026, prices found for a 1-night stay for 2 adults at Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis on May 7, 2026 start from $481, 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. 95 out of 96 reviews
Rating 8 - Good. 0 out of 96 reviews
Rating 6 - Okay. 0 out of 96 reviews
Rating 4 - Poor. 0 out of 96 reviews
Rating 2 - Terrible. 1 out of 96 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

10/10 Excellent

Steven B.

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

10/10 Excellent

Betsy Dinan W.

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

10/10 Excellent

Lauren K.

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

10/10 Excellent

Brad H.

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

10/10 Excellent

kaya r.

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

Clean & cozy

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

10/10 Excellent

Bethany M.

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

10/10 Excellent

Susan M.

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

Wonderful VRBO

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

10/10 Excellent

Lauren M.

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

10/10 Excellent

Susan M.

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

Beautiful place

Wonderful
Stayed 4 nights in Sep 2023
Verified

10/10 Excellent

Karen S.

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

10/10 Excellent

Errol L.

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

10/10 Excellent

Ryan C.

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

10/10 Excellent

Tina

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

10/10 Excellent

Hernan

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

10/10 Excellent

Keyvan

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

10/10 Excellent

Judy C.

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

10/10 Excellent

Gara S.

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

10/10 Excellent

Jennifer W.

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
Verified

10/10 Excellent

Lauren

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

10/10 Excellent

Maryann J.

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

10/10 Excellent

Jim W.

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

Lovely!

Spotless, super comfortable, and very lovely owners. A stone's throw from a little private "beach" with fishing pier and playground. It was great!
Stayed 2 nights in Feb 2021
Verified

10/10 Excellent

robert w.

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

10/10 Excellent

Maria A.

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

10/10 Excellent

Ashley A.

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
Verified

10/10 Excellent

Lauren M.

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

About the host

Hosted by Winston & Carolyn

Host profile image

Premier Host

They consistently provide great experiences for their guests
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