See all properties
Entire home

Chesapeake Bay Retreat W/Breathtaking Views

Family-friendly stay near Chesapeake Bay

Choose dates to view prices

Photo gallery for Chesapeake Bay Retreat W/Breathtaking Views

A kitchen with a large island, bar stools, and a view of the ocean.
A modern 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 hallway with a wooden floor, a bench, a door, and a glass door leading outside.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathrooms2866 sq ft

Popular amenities

  • Ocean view
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Rock Hall, MD
  • Place, The Mainstay
    ‪12 min drive‬
  • Place, Rock Hall Harbor
    ‪13 min drive‬
  • Place, Waterman’s Museum
    ‪13 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪151 min drive‬

Room options

About the neighborhood

Rock Hall

Oceanside stay.Within a 5-minute walk of the vacation home, you'll find Chesapeake Bay and Northern Chesapeake Bay. The Mainstay and Rock Hall Harbor are also within 6 miles (10 km).
View more Vacation Homes in Rock HallOpens in a new window

What's nearby

  • The Mainstay - 12 min drive - 6.9 miles
  • Rock Hall Harbor - 13 min drive - 7.3 miles
  • Waterman’s Museum - 13 min drive - 7.3 miles
  • Ferry Park - 14 min drive - 8.2 miles
  • beach near Ferry Park - 14 min drive - 8.2 miles

Getting around

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

Restaurants

  • ‪Harbor Shack - ‬14 min drive
  • ‪Admiral’s Club Beachside Bar - ‬15 min drive
  • ‪Ford's Seafood - ‬12 min drive
  • ‪Chester River Seafood - ‬18 min drive
  • ‪Waterman's Crab House - ‬13 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.

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

Similar properties

A covered outdoor seating area with a view of a landscaped garden and a body of water.
Inn at Haven Harbour
Rock Hall
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.0 out of 5, Very Good, 5 reviews
Inn at Haven Harbour

Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Games
  • Smart TV
  • Stereo

Outdoor areas

  • Barbecue grill
  • Garden

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • No elevator (single-level property)
  • Single level property
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In a rural location
  • In a village
  • Near the ocean
  • On the waterfront

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

  • Double-glazed windows
  • Garden
  • Recycling
  • Some LED lighting used
  • Unit size: 2,866 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 10:00 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 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.

Rules

✅ 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

Pets

  • Pets are welcome
  • Maximum 2 (weight limit: 50 lbs per pet)
  • Service animals are exempt from fees

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
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

8a000c0e-26f3-4658-b4cb-26850163ddf4

Frequently asked questions

How close is Chesapeake Bay Retreat W/Breathtaking Views to the airport?

This vacation home is 94.9 mi (145-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does Chesapeake Bay Retreat W/Breathtaking Views have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does Chesapeake Bay Retreat W/Breathtaking Views offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Chesapeake Bay Retreat W/Breathtaking Views?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Chesapeake Bay Retreat W/Breathtaking Views?

Free parking is not available at this vacation home.

Does Chesapeake Bay Retreat W/Breathtaking Views have a pool?

This vacation home does not have a pool.

Does Chesapeake Bay Retreat W/Breathtaking Views have a spa?

There are no spa services available at this vacation home.

How close is Chesapeake Bay Retreat W/Breathtaking Views to downtown Rock Hall?

This vacation home is 3.3 mi away from Rock Hall.

Chesapeake Bay Retreat W/Breathtaking Views Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

William J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was such a wonderful break from City life! Place was amazing! Community was amazing people in the small town were so nice! We’ll definitely be back! The place is amazing!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

josh b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home situated right on the water with everything we could need. Would not hesitate to return!
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

ashish n.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic location for a quiet getaway. Loved the home- very comfortable, well maintained and stocked and cared for. Joeann was most kind and helpful with all the information we neededThe highlight was the amazing sightings of bald eagles over the bay. Thank you!
Stayed 3 nights in Jul 2026

Explore More Ways to Travel with Travelocity