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

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Beach nearby, sun-loungers, beach towels - Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis (Annapolis)
Interior - Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis (Annapolis)
Exterior detail - Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis (Annapolis)
Fridge, microwave, oven, stovetop - Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis (Annapolis)
Children’s area - Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis (Annapolis)
Nestled in a private beach community off the Chesapeake Bay, The Anchors offers a serene water view escape. Whether you're looking to recharge or enjoy water sports, this cozy cottage is perfect for relaxation and fun. With its fully-equipped kitchen and nearby restaurants, you'll have everything needed to prepare meals or store leftovers.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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.

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"!

Property amenities

Beach

  • Beach nearby
  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car required
  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Video games

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 3 accessible parking spaces
  • No lift
  • Single level property
  • Wheelchair-accessible parking
  • Wheelchair-accessible path of travel
  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Meal delivery service

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina

Things to do

  • Tennis
  • Basketball nearby
  • Birdwatching nearby
  • Casino nearby
  • Cycling nearby
  • Fishing nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Surfing/bodyboarding nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

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
  • Deadbolt lock

General

  • Garden

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  • Free Wi-Fi
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  • Air-conditioning
9.0 out of 10, Wonderful, 1,855 reviews
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Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in and check-out are available

Minimum check-in age - 25

Check-out

Check-out before 10:30 AM

Special check-in instructions

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

Information provided by the property may be translated using automated translation tools

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.

Rules

Please do rearrange any furniture.

To avoid additional fees, do not allow additional guest to stay overnight.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

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
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

We should mention

This property does not have any lifts
A car is required for transport to and from this property

About the area

Located near the beach, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. Historical Society of Talbot County and Kunta Kinte Plaque & Alex Haley Memorial are local landmarks, and travellers 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 waterskiing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby. Visit our Annapolis travel guide
View more Holiday homes in Annapolis
Map
Annapolis, MD

What's nearby

  • Maryland Quiet Waters Park
    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
  • Royal Farms
    8 min drive
  • Starbucks
    5 min drive
  • Oscar’s Coffee
    10 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 is parking at Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis ?

On-site 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 ?

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 steps away from Chesapeake Bay and Northern Chesapeake Bay. Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park are also within 3 miles (5 km).

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

Reviews

Exceptional

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. 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

Cleanliness

10

Location

10

Property conditions & facilities

Reviews

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

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

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

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

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

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

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
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

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

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

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

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