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Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Photo gallery for Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Pool closed in winter and virtually staged because it was closed during pic.
Exterior
Private kitchen
Interior
Exterior detail

Reviews

8.8 out of 10
Excellent
2 bedrooms1+ bathroomSleeps 7

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Elkton, MD
  • Place, Chesland Park
    ‪5 min drive‬
  • Place, Brantwood Park
    ‪5 min drive‬
  • Place, Elkton Golf and Batting Center
    ‪8 min drive‬
  • Airport, Wilmington, DE (ILG-New Castle)
    ‪26 min drive‬

Rooms & beds

2 bedrooms (sleeps 7)

Bedroom 2

2 Twin Bunk Beds

Living Room 1

2 Double Sofa Beds

Main Bedroom

1 Queen Bed

1 bathroom, 1 half bathroom

Bathroom 2

Toilet

Main Bath

Towels provided · Bathtub or shower · Bathtub · Toilet · Shower only · Hair dryer

Spaces

Deck or patio
Kitchen

About this property

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Welcome to our beautiful getaway located on the water in a peaceful wooded setting. Our home is situated on over an acre of land, offering plenty of privacy and serene natural surroundings. Inside, you'll find a spacious and inviting open floor plan, with hardwood floors and stylish décor. Outside, you'll find a private oasis, with a large deck overlooking the water and a sparkling pool. There are plenty of outdoor activities to enjoy, from swimming and fishing in the water to hiking and exploring the woods. Our home has been totally renovated and is well-maintained, so you can be sure that you'll have a comfortable and enjoyable stay. We look forward to welcoming you! 10 Minutes from Chesapeake Inn!
Our prices include all fees. No hidden fees.

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House Rules

Check in after 3:00 PM
Check out before 11:00 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: dogs (limit 2 total)
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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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Elkton

Elkton is home to this cottage. Historical Society of Cecil County and South Chesapeake City Historic District are local landmarks, and travelers looking to shop may want to visit Christiana Mall and Newark Shopping Center. Delaware Rock Gym and Fred Rust Ice Arena are also worth visiting.
View more Cottages in ElktonOpens in a new window
Map
Elkton, MD

What's nearby

  • Chesland Park - 5 min drive - 3.2 km
  • Brantwood Park - 5 min drive - 4.2 km
  • Meadow Park - 8 min drive - 5.2 km
  • Elkton Golf and Batting Center - 8 min drive - 5.2 km
  • Cow Pond - 9 min drive - 6.9 km

Getting around

  • Newark Station - 23 min drive
  • Wilmington, DE (ILG-New Castle) - 30 min drive

Restaurants

  • ‪Wawa - ‬11 min drive
  • ‪McDonald's - ‬11 min drive
  • ‪Royal Farms - ‬10 min drive
  • ‪Dunkin' - ‬11 min drive
  • ‪Starbucks - ‬10 min drive

Frequently asked questions

Does Chesapeake City Pool Retreat – Waterfront Stay in the Woods have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Chesapeake City Pool Retreat – Waterfront Stay in the Woods?

As of Apr 8, 2026, prices found for a 1-night stay for 2 adults at Chesapeake City Pool Retreat – Waterfront Stay in the Woods on Apr 27, 2026 start from $367, 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 Chesapeake City Pool Retreat – Waterfront Stay in the Woods pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking?

Onsite parking is available at the property.

What time is check-in at Chesapeake City Pool Retreat – Waterfront Stay in the Woods?

Check-in begins at 3:00 PM.

What time is check-out at Chesapeake City Pool Retreat – Waterfront Stay in the Woods?

Check-out is at 11:00 AM.

Where is Chesapeake City Pool Retreat – Waterfront Stay in the Woods located?

Situated in Elkton, this cottage is 1.6 mi (2.6 km) from Chesland Park and within 6 mi (10 km) of Elk Forest Wildlife Management Area and Chesapeake City Bridge. Meadow Park and Union Hospital are also within 6 mi (10 km).

Reviews

8.8

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 8 out of 15 reviews
Rating 8 - Good. 5 out of 15 reviews
Rating 6 - Okay. 1 out of 15 reviews
Rating 4 - Poor. 1 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.2/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.0/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Renae R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely place. We really enjoyed our stay
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Manuel Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place
Stayed 2 nights in Apr 2025
Verified

8/10 Good

Jean M.

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

Relaxing Escape

We loved having our own private pool with beautiful scenery! Very fun and relaxing stay.
Stayed 7 nights in Jul 2025
Verified

8/10 Good

Nate W.

Liked: Check-in, communication, location, listing accuracy
House was nice and clean. Location was good for trails and parks.
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Kim W.

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

Awesome time

The place was nice and the pool was great kids fished off the dock and caught a couple of fish
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Kathryn L.

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

Great stay

Great location right on the water. Great for fishing or just sitting and relaxing. The house is in a quiet secluded area but only 10 minutes from Chesapeake Bay. Pool was an awesome extra. My son enjoyed it. The home was clean and plenty of space.
Stayed 3 nights in May 2025
Verified

8/10 Good

Craig C.

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

Great property and even better property manager!

Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool.
Stayed 7 nights in Jul 2023
Verified

8/10 Good

Martin F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stay was great. Only negative was pool was not usable due to there being no cover, so a lot of leaves and a frog in there. The property manager (Brian) was amazing and did all he could to help, and immediately instacarted us anything we needed. Still, no pool when weather was nice was a disappointment, and the outdoor dock could use some work and cleaning too. Overall. Great stay and we'd recommend to others.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Michael O.

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

Perfect vacation spot and location..!

Had a great time at the house. Brian was super helpful and a pleasure to deal with. House was great. We enjoyed being right on the water & the pool. We will definitely be back..!
Stayed 4 nights in Jun 2023
Verified

10/10 Excellent

Marie G.

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

Quick Getaway

We checked in for a extended weekend getaway. Overall the house was in great condition clean, comfortable and cozy. Brian contacted us prior to arriving and was extremely helpful. Overall wonderful weekend would definitely stay again.
Stayed 2 nights in Aug 2023
Verified

10/10 Excellent

k. l.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place is modern yet a little rustic. The location is great. Close enough to Chesapeake City to drive over for a walk and coffee. Within ten minutes the other direction there’s a large grocery store and liquor store. The creek is in the backyard and it’s fun to sit on the dock and watch the birds. There are floats for the pool, but we didn’t have a warm enough day to get in. Really lovely place.
View from the living room window.
The deck is really big and there’s a large assortment of chairs to relax in.
Stayed 2 nights in Jun 2025
Verified

4/10 Poor

Ray M.

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy
The only reason I rented the property was the pool. I’m 74 and my wife is 71. The pool did not have handrails to get in or out of the pool which is a violation of regulations for Maryland. We could not use the pool because of this unsafe condition. Also the path down the the water was extremely steep with no steps.
Stayed 3 nights in Aug 2025
Verified

6/10 Okay

Kathy M.

Liked: Cleanliness, check-in, communication, location

Chesapeake

Overall, our mini vacation was awesome. Initially, we did have a problem with the heat. However, the host was very responsive!!! The views are so refreshing and natural. The location is close to restaurants and any other outings! Before going, check supplies!
Stayed 3 nights in Mar 2023
Verified

10/10 Excellent

Kathy R.

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

Family visit

This house has been beautifully renovated inside, it is very comfortable and cozy. It offers large windows on the front and back with views of the river. We had a fire in the real wood burning fireplace one morning when it was chilly outside. We spent Easter Sunday on the large deck enjoying the sunshine. There is a lovely pool, which we did not use. The location is very convenient to Middletown, DE and Elkton, MD; we could get to either location within 20 minutes. A fresh produce market, restaurant, ice cream shop, and park are within 5 minutes. It was quiet and peaceful during our visit. Brian was very responsive and gracious in communication.
Stayed 6 nights in Apr 2023
Verified

8/10 Good

Crystal D.

Stayed 4 nights in May 2025

About the host

Hosted by BRIAN

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