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

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

A waterfront property with a dock, a large house with a covered porch, and a well-maintained lawn.
A house with a large glass conservatory, a fenced yard, and a lake view.
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.
A spacious kitchen with wooden cabinets, a large island, and a stone backsplash.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.

Popular amenities

  • Private pool
  • Patio
  • Barbecue
  • Air-conditioning
  • Refrigerator
  • Onsite parking available

Explore the area

View map
Chestertown, MD
  • Place, Washington College
    ‪17 min drive‬
  • Place, River Arts Chestertown
    ‪18 min drive‬
  • Place, Chestertown Historic District
    ‪19 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪125 min drive‬

Rooms & beds

5 bedrooms (sleeps 7)

Bedroom 1

1 Queen Bed and 1 Single Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 Single Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo

Bathroom 3

Soap · Towels provided · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area

Add dates for prices

Similar properties

An early summer afternoon viewed from our porch.
Eastern shore beachfront cottage with stunning sunset views!
Worton
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
10.0 out of 10, Exceptional, (16 reviews)
Eastern shore beachfront cottage with stunning sunset views!

About the area

Chestertown

Located in Chestertown, this holiday home is on the waterfront. Rock Hall Harbor and Rolphs Wharf Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Chestertown Historic District. Larrabee Arts Center and Garfield Center for the Arts at the Prince Theater are also worth visiting. Discover the area's water adventures with kayaking, power boating and sailing nearby, or enjoy the great outdoors with hiking.
View more Holiday homes in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Washington College - 17 min drive - 16.2 km
  • River Arts Chestertown - 18 min drive - 17.6 km
  • Chestertown Historic District - 19 min drive - 18.0 km
  • Historical Society of Kent County Maryland - 19 min drive - 18.0 km
  • Rock Hall Harbor - 26 min drive - 23.2 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

Frequently asked questions

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

Yes, this property has an outdoor pool.

How much does it cost to stay at A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.?

As of 5 Nov 2026, prices found for a 1-night stay for 2 adults at A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. on 10 Mar 2027 start from AU$3,155, 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.

Is A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. pet-friendly?

No, only service animals are welcome at the property.

How much is parking at A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown.?

On-site parking is available at the property.

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.

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

Checkout is at 11:00 AM.

Where is A Waterfront Retreat with pier and pool. Spacious 4 bedrooms near Chestertown. located?

Situated on the waterfront, this holiday home is within 12 miles (20 km) of Washington College, Larrabee Arts Center and Chestertown Farmers Market. Garfield Center for the Arts at the Prince Theater and Schooner Sultana are also within 12 miles (20 km).

Reviews

9.8

Exceptional

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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is the perfect get away for a family. If you love the bird life and relaxing vacation this is the spot.
Stayed 4 nights in Aug 2026
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
Verified review

8/10 Good

Stayed 5 nights in Jul 2026
Tell us how we can improve our siteShare feedback