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Chesapeake Bay Retreat W/Breathtaking Views

Photo gallery for Chesapeake Bay Retreat W/Breathtaking Views

A kitchen with a large island, bar stools, and a view of the ocean.
A spacious living area with a large sofa, a coffee table, and a fireplace. There are multiple windows providing natural light and a view of the outdoors.
A spacious room with a pool table, a piano, and large windows offering a view of the sea.
A modern kitchen with a large island, bar stools, and a view of the ocean.
Exterior

Reviews

10 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
Sleeps 7•3 bedrooms•5 beds

Popular amenities

  • Hot tub on site
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washer
  • Air conditioning

Explore the area

View in a map
Rock Hall, MD

Rooms & beds

3 bedrooms (sleeps 7)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Twin Beds

Living room 1

1 Twin Bed

2 bathrooms

Bathroom 1

Bathroom 2

Spaces

Kitchen
Office
Garden
Dining area

About this property

Chesapeake Bay Retreat W/Breathtaking Views

Escape to serenity on the shores of Chesapeake Bay! This luxurious, multimillion-dollar waterfront retreat offers sweeping water views, upscale furnishings, and timeless historic charm. Minutes from vibrant Rock Hall and Chestertown. Relax on the deck with morning coffee, stroll or bike the scenic waterfront paths, enjoy sun dips at Ferry Park beach, catch live performances at The Mainstay, or explore birdwatching trails at Eastern Neck Wildlife Refuge.

I am here for you during your stay. Our level of interaction is up to you. I’m only a phone call/message away. You will be able to self check-in upon arrival.

✔ Exclusive use of the entire home offering complete privacy

✔ Spacious backyard with a fire pit for gatherings under the stars

✔ parking on the premises

✔ Effortless check-in process with a private entrance

Beachfront but no access to the beach unsafe for swimming. Nearby beach to swim in located on Beach Road / ferry park

**NO basement access***

FIRST FLOOR:

Master bedroom with King bed. Master bathroom attached.

Queen bedroom.

Living room has a trundle.

2nd floor: Loft area has twin beds. No door: just a stairwell the way it shows in photos.


✔ Spacious open-plan home with large windows flooding rooms with light
✔ Stylish Luxury furnishings providing a cozy and contemporary feel

✔️Fully-equipped kitchen
✔️ A private backyard oasis with a access to beach (please do not swim) deck & fire pit

✔ Pet-friendly ; Must provide upon booking
✔ Indoor fireplace to snuggle up during cooler evenings

✔ Explore the historic charm of nearby Chestertown and its unique local shops
✔ Visit scenic Rock Hall for a slice of nautical history
✔ Beach activities abound, from lounging on the sand to water sports
✔ Proximity to hiking and nature trails offering outdoor adventure

Please remember that you’re staying in a house not a hotel. Please treat the space with respect. This is a quiet secluded neighborhood, so please be mindful of our neighbors. No noise after 10PM!

If any problems arise, we will do our best to take action ASAP, but there is no one living on site 24/7.

The entire house is yours, please respect the locked closets. No access to basement.


The cleaning fee goes directly to our amazing cleaner.

The house is on a private driveway please go 13 MPH
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: less than 50 lbs per pet (limit 2 pets total)
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
Failure to complete these may result in a negative review from the host.
✅ Allowed • Registered guests only on the property • Pets allowed (with pre-approval and fee, if applicable) • Fishing from our dock is welcome
🕒 Check-in & Check-out • Check-in: 4:00 PM • Check-out: 10:00 AM
• No swimming from our dock – fishing only • No parties or events

Important information

You need to know

Property # 4607016
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

Rock Hall

Located in Rock Hall, this vacation home is in a rural area and on the waterfront. The Mainstay and Waterman’s Museum are cultural highlights, and some of the area's activities can be experienced at Rock Hall Harbor and Bill's Yacht Basin. Traveling with kids? Consider Larrabee Arts Center and Garfield Center for the Arts at the Prince Theater.
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Map
Rock Hall, MD

Getting around

  • Baltimore, MD (MTN-Martin State) - 145 min drive

Restaurants

  • ‪Admiral’s Club Beachside Bar - ‬15 min drive
  • ‪Ford's Seafood - ‬12 min drive
  • ‪Chester River Seafood - ‬18 min drive
  • ‪American Legion - Post 228 - ‬12 min drive
  • ‪Osprey Point Restaurant - ‬14 min drive

Frequently asked questions

Is Chesapeake Bay Retreat W/Breathtaking Views pet-friendly?

Yes, this property allows pets (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much does it cost to stay at Chesapeake Bay Retreat W/Breathtaking Views?

As of Aug 26, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Bay Retreat W/Breathtaking Views on Sep 6, 2026 start from $695, 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 Chesapeake Bay Retreat W/Breathtaking Views?

Check-in begins at 4:00 PM.

What time is check-out at Chesapeake Bay Retreat W/Breathtaking Views?

Check-out is at 10:00 AM.

Where is Chesapeake Bay Retreat W/Breathtaking Views located?

This family-friendly Rock Hall vacation home is located on the waterfront, just steps from Chesapeake Bay and Northern Chesapeake Bay. The Mainstay and Waterman’s Museum are also within 6 mi (10 km).

About the host

Hosted by JOEANNA NAPOLES

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