Entire home

Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis

Choose dates to view prices

Where to?

Dates

August 2025

September 2025

Beach nearby, sun loungers, beach towels

Overview
Amenities
Policies
Location
Host

Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4

Popular amenities

Barbecue grill
Washer
Dryer
Kitchen
Parking available
Outdoor Space

Explore the area

Annapolis, MD

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

Room options

About the neighborhood

Annapolis

Located in Oyster Harbor, this vacation home is within a few miles (5 km) of sights such as Bay Bridge Market Place Shopping Center and Maryland Quiet Waters Park. The vacation home includes a kitchen, a refrigerator, and a microwave.

View more Vacation Homes in Annapolis

What's nearby

Maryland Quiet Waters Park - 5 min drive - 2.4 miles
Annapolis City Dock - 10 min drive - 5.1 miles
Annapolis Maritime Museum - 10 min drive - 4.7 miles
U.S. Naval Academy - 11 min drive - 4.9 miles
Navy-Marine Corps Memorial Stadium - 12 min drive - 6.6 miles

Getting around

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

Restaurants

‪McDonald's - ‬5 min drive
‪Little Italy Annapolis - ‬7 min drive
‪Boatyard Bar & Grill - ‬9 min drive
‪Carrol's Creek Cafe - ‬9 min drive
‪Annapolis Yacht Club - ‬9 min drive

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 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"!

The vacation home is air-conditioned and features a kitchen and space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

Property manager

Winston & Carolyn

Similar properties

Kitchen
Washer
Dryer
Free WiFi

Air conditioning
Laundry
Parking available
Microwave

$417 nightly

Aug 7 - Aug 8

Total includes taxes and fees

Property amenities

Beach

Beach nearby
Beach loungers
Beach towels

Internet

Available in the house: Free WiFi

Parking and transportation

Car required
Parking on site

Kitchen

Blender
Coffee grinder
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Ice maker
Kitchen island
Microwave
Oven
Paper towels
Refrigerator
Spices
Stovetop
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.
Single level property
Smoking not allowed

Services and conveniences

Iron/ironing board
Meal delivery service

Location highlights

Near a health/beauty spa
Near a hospital
Near an outlet shopping mall
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

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in 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

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

Pets

This property doesn't allow pets

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

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

Check-in: 4:00 PM
Check-out: 10:30 AM
Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

This property is managed by a private host, not a professional engaged in trade or business.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Property is also known as

Cozy Cottage Beach House Annapolis

Cozy Cottage Beach Annapolis

Cozy Cottage by the Beach

Cozy Cottage by the Beach Minutes From Downtown Annapolis

Cozy Cottage by the Beach Minutes from Downtown Annapolis

Frequently asked questions

What's there to see within easy reach of this vacation home?

This vacation home is situated in Oyster Harbor, close to Bay Ridge Beach, Maryland Quiet Waters Park, and Annapolis Landing Marina. You'll also find Annapolis Maritime Museum and Annapolis City Dock within a short drive.

Is parking available on site at this vacation home?

No, there isn't parking at this vacation home.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Is Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis good for couples?

Amenities that appeal to couples at this vacation home include a kitchen, a meal delivery service, and a smart TV.

Does Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis have a hot tub?

No, this vacation home doesn't have a spa tub.

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at this vacation home?

No, this vacation home doesn't feature connecting guestrooms.

What is the closest airport to this vacation home?

The closest major airport to this vacation home is Fort Meade, MD (FME-Tipton), which is 23.3 mi away (31 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is located 28.2 mi away (38-minute drive).

Are there rooms with balconies at Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis ?

No, there aren't any accommodations with balconies at Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis .

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

Exceptional

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness

10/10 Excellent

Michelle K.

Jul 26, 2025

Liked: Cleanliness

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

Susan S.

Jul 14, 2025

Liked: Cleanliness

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

Maryann J.

May 24, 2025

Liked: Cleanliness

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

Bethany M.

Oct 19, 2024

Liked: Cleanliness

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.

Sep 8, 2024

Liked: Cleanliness

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

Betsy Dinan W.

Sep 2, 2024

Liked: Cleanliness

Great weekend getaway!

Great property and great time in Oyster Harbour!

Stayed 2 nights in Aug 2024

10/10 Excellent

Paul D.

Aug 20, 2024

Liked: Cleanliness

Stayed 2 nights in Jun 2024

10/10 Excellent

Laura K.

Aug 20, 2024

Liked: Cleanliness

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

Paige A.

Aug 11, 2024

Liked: Cleanliness

Stayed 3 nights in Jun 2024

10/10 Excellent

Jennifer S.

Jul 8, 2024

Liked: Cleanliness

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., Annapolis

Jun 21, 2024

Liked: Cleanliness

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.

Jun 13, 2024

Liked: Cleanliness

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, Katy

Traveled with family

Jun 1, 2024

Liked: Cleanliness, amenities, property conditions & facilities

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.

Oct 23, 2023

Liked: Cleanliness

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.

Oct 8, 2023

Liked: Cleanliness

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.

Oct 1, 2023

Liked: Cleanliness

Beautiful place

Wonderful

Stayed 4 nights in Sep 2023

10/10 Excellent

Betty S.

Sep 5, 2023

Liked: Cleanliness

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

Ryan C.

Aug 2, 2023

Liked: Cleanliness

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

Steven B.

Jul 29, 2023

Liked: Cleanliness

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.

Jul 18, 2023

Liked: Cleanliness

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

10/10 Excellent

kaya r.

Jun 29, 2023

Liked: Cleanliness

Clean & cozy

Great location, clean and cozy.

Stayed 2 nights in Jun 2023

10/10 Excellent

Karen S.

Jun 24, 2023

Liked: Cleanliness

Tranquility and comfort

Nicely equipped, very comfortable and lovely location.

Stayed 6 nights in Jun 2023

10/10 Excellent

Tina

Traveled with group

Jun 21, 2023

Liked: Cleanliness, amenities, property conditions & facilities

The property was quaint and nicely appointed. Comfortable and clean. Hosts were wonderful!

10/10 Excellent

Ling P.

May 28, 2023

Liked: Cleanliness

What a pleasant stay

I rented this house almost 2 years ago for my mid’s commission week. The Winston couple are the best host of Annapolis I have met in the past 4 years. The house is spotless and has everything we need. We held a postgraduation party and Winston couple helped us to turn it to successful party. What a pleasant stay!! I believe that Winston couple become our friends and we definitely will come back in the future.

Stayed 8 nights in May 2023