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Chesapeake City Pool Retreat – Waterfront Stay in the Woods

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A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave. There is a dining area with white chairs and a gray sofa. A flat-screen TV is mounted on the wall, and a ceiling fan is visible.
A modern kitchen with a central island, a stone fireplace, and a view of the outdoors.
A room with a large window overlooking a deck and a river, a gray sofa, a flat-screen TV, and a sign indicating the location.
A modern kitchen with white cabinets, a large island with bar stools, stainless steel appliances, and pendant lighting.
A cozy living room with a grey sofa, white chairs, a round table, and a large window.

Reviews

8.8 out of 10
Excellent

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
  • Dog-friendly
  • Refrigerator
  • Internet
  • Onsite parking available

Explore the area

View map
Elkton, MD
  • Place, Chesland Park
    ‪5 min drive‬
  • Place, Brantwood Park
    ‪5 min drive‬
  • Place, Meadow Park
    ‪8 min drive‬
  • Airport, Wilmington, DE (ILG-New Castle)
    ‪30 min drive‬

Rooms & beds

2 bedrooms (sleeps 7)

Bedroom 2

2 Single 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
Number of living rooms

Add dates for prices

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About the area

Elkton

Elkton is home to this cottage. Historical Society of Cecil County and South Chesapeake City Historic District are local landmarks, and travellers looking to shop may want to visit Christiana Mall and Newark Shopping Center. Elkton Golf and Batting Center and Delaware Rock Gym are also worth visiting.
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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 - 6.9 km
  • Elkton Golf and Batting Center - 8 min drive - 6.9 km
  • West Meadow Park - 9 min drive - 8.7 km

Getting around

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

Restaurants

  • ‪Wawa - ‬11 min drive
  • ‪Chick-fil-A - ‬13 min drive
  • ‪McDonald's - ‬11 min drive
  • ‪Royal Farms - ‬10 min drive
  • ‪McDonald's - ‬13 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 1 November 2026, prices found for a 1-night stay for 2 adults at Chesapeake City Pool Retreat – Waterfront Stay in the Woods on 5 February 2027 start from NZ$2,526, 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 at Chesapeake City Pool Retreat – Waterfront Stay in the Woods?

On-site 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?

Checkout 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 2.7 mi (4.4 km) from Brantwood Park. Elk Forest Wildlife Management Area and Elkton Golf and Batting Center are also within 6 miles (10 km).

Reviews

8.8

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 9 out of 16 reviews
Rating 8 - Good. 5 out of 16 reviews
Rating 6 - Okay. 1 out of 16 reviews
Rating 4 - Poor. 1 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

9.2/10

Cleanliness

10/10

Check-in

10/10

Communication

9.4/10

Location

9.2/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay, the house was super clean, the property is on a dead end lane, so it was very quiet and peaceful, no road noise. Very pretty setting being right on the water. The pool and deck area was spacious and nice to hang out on. We also brought our dog and plenty of space to walk her, we had a very nice time.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

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

10/10 Excellent

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

8/10 Good

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 review

8/10 Good

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 review

10/10 Excellent

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 review

8/10 Good

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

8/10 Good

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 review

6/10 Okay

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
Response from VrboOwner on 1 May 2023
Thanks for the feedback Kathy! The entire hvac system was replaced. Also, after talking with you, I had emergency tech come and repair unit within ann hour and completely refunded you for the night.
Verified review

4/10 Poor

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 review

10/10 Excellent

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
Response from VrboOwner on 1 May 2023
Thank you! So happy to host such a lovely family. Please come back soon!
Verified review

8/10 Good

Stayed 4 nights in May 2025
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