Entire home

Cozy Cottage by the Beach - Waterview Minutes from Downtown Annapolis

Overview
Amenities
Policies
Location
Host

Exceptional

2 bedrooms1 bathroomSleeps 4

Popular amenities

Dryer
Washer
Kitchen
Parking available
Barbecue grill
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)
‪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 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"!

Property manager

Winston & Carolyn

Premier Host

Add dates for prices

Amenities

Kitchen

Washing machine

Dryer

Free WiFi

Air conditioning

Outdoor space

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Kitchen
Washer
Dryer
Free WiFi

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:30 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

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. 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

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

‪McDonald's - ‬5 min drive
‪Bay Ridge Wine & Spirits - ‬5 min drive
‪Royal Farms - ‬8 min drive
‪Davis' Pub - ‬9 min drive
‪Oscar’s Coffee - ‬10 min drive

Frequently asked questions

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:30 AM.

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

Located in Oyster Harbor, this holiday home is within 3 miles (5 km) of Bay Bridge Market Place Shopping Center, Maryland Quiet Waters Park and Historic Mount Moriah AME Church. Historical Society of Talbot County and Annapolis Golf Club are also within 3 miles (5 km).

Exceptional

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

Learn more

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

10/10 Excellent

Errol L.

13 Aug, 2025

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

Betsy Dinan W.

2 Sept, 2024

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.

24 May, 2025

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

Michelle K.

26 Jul, 2025

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

Lauren K.

21 Jun, 2024

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

Bethany M.

19 Oct, 2024

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

Susan S.

14 Jul, 2025

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

Susan M.

1 Oct, 2023

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

Beautiful place

Wonderful

Stayed 4 nights in Sep 2023

10/10 Excellent

Susan M.

1 May, 2023

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

Wonderful VRBO

Quiet neighborhood, beautiful home

Stayed 5 nights in Apr 2023

10/10 Excellent

Lauren M.

29 Mar, 2023

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

Karen S.

24 Jun, 2023

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

Tranquility and comfort

Nicely equipped, very comfortable and lovely location.

Stayed 6 nights in Jun 2023

10/10 Excellent

Ryan C.

2 Aug, 2023

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

Judy C.

13 Jun, 2024

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

Tina

21 Jun, 2023

Liked: Cleanliness, amenities, property conditions & facilities, communication

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

10/10 Excellent

Gara S.

8 Oct, 2023

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

Hernan

26 Sept, 2022

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

10/10 Excellent

Jennifer S.

8 Jul, 2024

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

Becky W.

8 Sept, 2024

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

Keyvan

6 Jul, 2022

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

10/10 Excellent

Jennifer W., Baltimore, MD

21 May, 2022

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

10/10 Excellent

Lauren

12 Sept, 2022

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

10/10 Excellent

robert w.

7 Mar, 2023

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

10/10 Excellent

Jim W.

2 Mar, 2021

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

Maria A.

21 Mar, 2021

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

10/10 Excellent

Lauren M.

23 Oct, 2023

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