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A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Chestertown vacation home with private pool

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Photo gallery for A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

A house with a large glass conservatory, a fenced yard, and a lake view.
A spacious kitchen with wooden cabinets, a large island, and a stone backsplash.
A cozy living room with a stone fireplace, leather sofa, and a painting above it.
A swimming pool with stone tiles, surrounded by grass and trees, with a view of a lake and a dock in the background.
A house with a dock extending into a body of water, surrounded by lush greenery.

Reviews

9.8 out of 10
Exceptional

Entire home

5 bedrooms3 bathrooms

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Chestertown, MD
  • Place, Washington College
    ‪14 min drive‬
  • Place, River Arts Chestertown
    ‪15 min drive‬
  • Place, Chestertown Historic District
    ‪16 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪122 min drive‬

Room options

About the area

Chestertown

On waterfront.You'll be within 9 miles (15 km) of Washington College and 12 miles (20 km) of Larrabee Arts Center. Chestertown Farmers Market and Garfield Center for the Arts at the Prince Theater are within 12 miles (20 km).
View more Vacation homes in ChestertownOpens in a new window

What's nearby

  • Washington College - 14 min drive - 16.2 km
  • River Arts Chestertown - 15 min drive - 17.6 km
  • Chestertown Historic District - 16 min drive - 18.0 km
  • Historical Society of Kent County Maryland - 16 min drive - 18.0 km
  • Garfield Center for the Arts at the Prince Theater - 16 min drive - 18.0 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 123 min drive

Restaurants

  • ‪Harbor Shack - ‬28 min drive
  • ‪Ford's Seafood - ‬25 min drive
  • ‪Waterman's Crab House - ‬27 min drive
  • ‪Chester River Seafood - ‬29 min drive
  • ‪Admiral’s Club Beachside Bar - ‬28 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.

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.

Welcome to Lovely Cove Farm. Close to Chestertown and Rock Hall for shopping and dining, but a world away. Secluded and serene spot for birders and boaters and stargazers. Bald eagles, osprey, herons, songbirds and migratory waterfowl can be seen as they go about their daily routines. And a public boat ramp is nearby. Come by boat or land. Enjoy a dip in your private pool before cooking in the gourmet kitchen. Or grilling outside on the gas grill. The skies at night are dark enough to enjoy constellations, meteors and the Milky Way so vividly and memorably.

Enter the house and be amazed with the views throughout with large windows overlooking East Langford Creek. There is a lovely living room which opens to the outdoor deck and screened-in porch. The first floor includes the living room, kitchen, dining area, a sitting room, powder room, and an office with a daybed.

The second floors have 2 staircases. The one has the master suite with ensuite bathroom. There is a Queen bed and a daybed. The main staircase takes you up to 3 more bedrooms and a hall full bathroom. Bedroom 2 has 2 twin beds. Bedroom 3 has a king bed, and bedroom 4 has a queen bed.

The pier can be used for fishing or crabbing. Or, to tie up your boat. There is a floating pier which can be used to launch the provided kayaks (2) or canoe.

The pool is for your personal use. Sorry, no daytime guests.

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Guest Suite for up to 2 in a Victorian on the Chester River
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  • Free WiFi
  • Air conditioning
  • Parking available
  • Water view
4.9 out of 5, Exceptional, 29 reviews
The price is CA $97
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includes taxes & fees
Oct 19 - Oct 20
Guest Suite for up to 2 in a Victorian on the Chester River

Property amenities

Pool/Spa

  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 2.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • DVD player
  • Smart TV with cable/satellite channels
  • Video library

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Service animals only (pets not 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 steps to reach entrance
  • Area rugs in public areas
  • Hardwood flooring in public areas
  • Tile flooring in public areas
  • Upper floors accessible by stairs only
  • Smoking not allowed

Location highlights

  • Near a hospital
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Kayak
  • Birdwatching nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Wildlife walks 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)
  • Fire extinguisher
  • First aid kit

General

  • Garden
  • Recycling

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 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
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, lock the doors, and return the keys
Failure to complete these may result in a negative review from the host.

Rules

This is not a party house and we ask that you use the property as you would any family home.
Being near the water, noise carries. Please respect the ambience of your surroundings by not having any loud voices, noise or music outside.
Please keep all exterior doors closed and keep food off counters to deter ants.

Pets

  • No pets allowed, but service animals are welcome

Children and extra beds

  • Children are welcome.
  • Note from host: The pool and waterfront are not fenced off.

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 and a first aid kit
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 private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Frequently asked questions

How close is A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. to the airport?

This vacation home is 86 mi (123-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.?

No, there is no casino at this vacation home.

What time is check-in at A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.?

Check-in begins at 4:00 PM.

Is there free parking at A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.?

Free parking is not available at this vacation home.

Does A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. have a pool?

This vacation home features an outdoor pool.

Does A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. have a spa?

There are no spa services available at this vacation home.

How close is A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. to downtown Chestertown?

This vacation home is 6.7 mi away from Chestertown.

A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 5 out of 6 reviews
Rating 8 - Good. 1 out of 6 reviews
Rating 6 - Okay. 0 out of 6 reviews
Rating 4 - Poor. 0 out of 6 reviews
Rating 2 - Terrible. 0 out of 6 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful house and stunning location. Very cozy in the winter and great for a family getaway. We loved the decor and homeiness. Hosts were responsive and kind. We want to come back in the summer!
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice amd well appointed
Stayed 4 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Check-in was seamless. It’s evident this house was built with love. Every detail was user friendly and artfully done. My family made memories that will last a lifetime.
Stayed 3 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our second time staying at this wonderful house and we loved it. The pool is huge and warm, the views are unbeatable, and the house and yard are so well taken care of. We loved grilling, fishing, crabbing, and jumping in the pool. It's such a special place!
Stayed 7 nights in Jul 2026

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