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

Holiday home in Annapolis with kitchen

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

Private kitchen
Living area
Interior
Living area
Living area

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen
  • Barbecue grill
  • Outdoor space

Explore the area

View map
Annapolis, MD
  • Place, Maryland Quiet Waters Park
    ‪5 min drive‬
  • Place, Annapolis City Dock
    ‪10 min drive‬
  • Place, U.S. Naval Academy
    ‪11 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪40 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

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"!

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Amenities

Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space

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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 to 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 rubbish
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
On-site parties or group events are strictly prohibited
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, a first aid kit and a deadlock

We should mention

A car is required for transport to and from this property

About the area

Annapolis

Located near the beach, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. Annapolis Golf Club and Annapolis Landing Marina are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Wild Bird Center and Annapolis Maritime Museum. French Soldiers Monument and Helen Avalynne Tawes Garden are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Annapolis, MD

What's nearby

  • Maryland Quiet Waters Park - 5 min drive - 3.8 km
  • Annapolis City Dock - 10 min drive - 8.2 km
  • Annapolis Maritime Museum - 10 min drive - 7.6 km
  • U.S. Naval Academy - 11 min drive - 7.9 km
  • Navy-Marine Corps Memorial Stadium - 12 min drive - 10.6 km

Getting around

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

Restaurants

  • ‪Bay Ridge Wine & Spirits - ‬5 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Starbucks - ‬5 min drive
  • ‪Main & Market - ‬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.

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 ?

Checkout is at 10:30 AM.

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

Located in Oyster Harbor, this holiday home is within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay. Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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

Eco-friendliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

10/10 Excellent

Michelle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect house in a perfect location! We drove from Long Island to visit friends in Severn on our way to NC. This house is perfectly situated on a quiet block across from a creek with beach access via a 5 min walk down the block. We met Winston and Carolyn and they were lovely! We look forward to staying at this house again the next time we visit our MD friends! Winston and Carolyn, thank you for making your home feel like our home! Especially with a 4 year old and 2.5 year old! See you soon :) —barely have pics because we were too busy having fun!!
Stayed 2 nights in Jul 2025

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

10/10 Excellent

Karen (Casey) S.

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

Adorable little house

We loved staying here! Everything is updated. Kitchen tools very high quality. Appreciated all the extras found in the pantry. Bed super comfy. Nice pillows. Backyard is lovely. Street is quaint and quiet. Quiet beach is a 5 minute walk away. We enjoyed hiking in Quiet Waters Park and Thomas Point Park also. Friendly neighbors and friendly owners who live next door!
Stayed 4 nights in Apr 2023

10/10 Excellent

Crystal F., Where do you live?

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

Love this cottage!

This was the perfect place for us to stay. We had a family event in the area and the cottage became the central meeting point for our extended family. The kids were able to let off some steam playing in the large back yard before heading down to the beach for a birthday party. The beach is truly within walking distance from the cottage. Kitchen is fully stocked - your choice of a Keurig, drip coffee maker, or a french press. Everything is neat and clean. Only caveat I would have - if you have mobility issues: the bathroom is on the small side and there are steps to gain entry into the cottage. Will definitely stay there again.
Stayed 3 nights in Jun 2019

10/10 Excellent

Brad H.

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

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

10/10 Excellent

Susan S.

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

Cozy cottage

My BFF and I very much enjoyed our four day stay at the anchors cozy cottage. The queen bed super soft and comfortable, was told the full size bed was a little firmer, but still just as good, cozy sheets, and bedding.Rain showerhead made the shower luxurious I felt very spoiled!TVs with streaming services in each room if you choose to use them.Excellent location you can see the water through the front of the house and it’s just a minute walk down the nice quiet road. Lots of people walking their dogs and bike riders.Private beach for the residence.The owners were very accommodating and answered any questions very quickly.I give this an A rating and would definitely stay again if back in the Annapolis area.
Stayed 3 nights in Jul 2025

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

10/10 Excellent

Becky W.

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

USNA Parents Weekend

It was nice to get outside DTA and see another part of Annapolis. 15 minutes from DTA it was quiet and beautiful small cottage perfect for our family. The home was clean and designed well. We would stay again. Thank you!!!
Stayed 2 nights in Sep 2024

10/10 Excellent

Laura K.

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

Immaculate and Comfortable Cottage By the Beach

We have stayed in many VRBO properties around the country and "The Anchors" is by far the most pleasant experience we have ever had. The cottage is immaculately clean, thoughtfully fitted out, and in a safe, quiet neighborhood. The beds are comfortable and there is plenty of hot water-these are the most important things we look for in a rental property. The rainfall shower is a pleasant touch! The owners, Carolyn and Winston, are tremendously gracious and accommodating. They made us feel very much at home in this jewel of a cottage! The neighborhood is very quiet and relaxed- you can actually feel your blood pressure go down as you arrive in this laid back community! Cannot wait to return!
Stayed 3 nights in Aug 2024

10/10 Excellent

Jennifer S.

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

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

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

10/10 Excellent

Cale

Liked: Cleanliness, amenities, property conditions & facilities, communication
This beautiful cozy little cottage is nestled in a delightful quiet private beach community. The Anchors (owners) are super friendly, attentive and quick to respond to you if you have any questions. Our family of 4 from Katy, Texas, stayed there for 1 week to celebrate our son’s commissioning week and graduation from the US Naval Academy and we thoroughly enjoyed our stay at their cottage. Grocery stores, restaurants, pharmacies, etc. are just minutes away. I highly recommend this beautiful cottage for any couple or small family that wishes to get away, unwind and enjoy the tranquility of a private beach community in beautiful Annapolis, Maryland.
Stayed 8 nights in May 2024

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

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

10/10 Excellent

Susan M.

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

Beautiful place

Wonderful
Stayed 4 nights in Sep 2023

10/10 Excellent

Betty S.

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

130th Anniversary of Highland Beach, MD

Excellent, had everything imaginable for my visit away from home, fabulous outdoor space, short distance to important events, no traffic, walk to beach. Very quiet and relaxing on a busy holiday weekend. Try it, you will love it. Sign up before i take your dates! I will return!
Stayed 3 nights in Sep 2023

10/10 Excellent

Steven B.

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

Great neighborhood

Immaculate little place, loved the neighborhood, quiet diverse with homeowners, family rentals, young people old people ethnicity diverse. The beach for the little community on Chesapeake Bay is small but nice , gated, is open until midnight had plenty of room for family parties, has a small play ground and volleyball owners were in touch but not intrusive, can’t find a single thing to complain about.
Stayed 3 nights in Jul 2023

10/10 Excellent

Kent C.

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

Oyster Harbor Gem

Winston and Carolyn are extremely nice and thoughtful hosts. The space feels larger than it is with two comfortable bedrooms a nice living area and kitchen. They had the bedrooms, kitchen, and bathrooms extremely well stocked and were very easy to communicate with. We loved Annapolis but it was wonderful to be away from Downtown in a very quiet and extremely friendly neighborhood. We will be back no doubt. Thank you so much Winston and Carolyn!
Stayed 3 nights in Jul 2023

About the host

Hosted by Winston & Carolyn

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Premier Host

They consistently provide great experiences for their guests
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