Entire home

Chesapeake Charm

Photo gallery for Chesapeake Charm

A patio area with Adirondack chairs, a fire pit, and a view of a lake.
A single-story house with a front porch, a garage, and a lawn.
A bedroom with a bed featuring a nautical-themed bedspread, a ceiling fan, and a window with curtains.
A living room with a white brick fireplace, a green armchair, a striped chair, and a wicker basket on the floor.
A kitchen with white cabinets, a microwave, a stove, a sink, and a window.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Cook, dine, and unwind
    Top-rated for its fully equipped kitchen, perfect for every meal.

Popular amenities

  • Patio
  • Dog-friendly
  • Barbecue grill
  • Air-conditioning
  • Garage parking available
  • Refrigerator

Explore the area

View in a map
Dameron, MD
  • Place, Saint Jerome Beach
    ‪19 min walk‬
  • Place, St. Mary's College of Maryland
    ‪17 min drive‬
  • Place, Point Lookout State Park
    ‪19 min drive‬

Rooms & beds

3 bedrooms (sleeps 9)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Single Beds

Bedroom 3

1 Queen Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet

Spaces

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

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About the area

Dameron

Located in Dameron, this holiday home is in a rural area and on the waterfront. Historic St. Mary's City and Patuxent River Naval Air Museum are cultural highlights, and some of the area's attractions include Montgomery Hall Fine Arts Center and Michael P. O'Brien Athletics and Recreation Center. Discover the area's water adventures with kayaking and waterskiing nearby, or enjoy the great outdoors with ecotours and cycling.
View more Holiday homes in DameronOpens in a new window
Map
Dameron, MD

What's nearby

  • Saint Jerome Beach - 19 min walk - 1.6 km
  • St. Mary's College of Maryland - 17 min drive - 18.5 km
  • Point Lookout State Park - 19 min drive - 21.4 km
  • Patuxent River Naval Air Station - 23 min drive - 28.9 km
  • Calvert Cliffs State Park - 50 min drive - 54.2 km

Restaurants

  • ‪St. James Deli - ‬13 min drive
  • ‪The Pub - ‬18 min drive
  • ‪Hacienda Los Guayabos - ‬14 min drive
  • ‪SALT Waterfront Kitchen - ‬16 min drive
  • ‪Pier450 - POV Restaurant - ‬15 min drive

Frequently asked questions

Is Chesapeake Charm pet-friendly?

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

How much does it cost to stay at Chesapeake Charm?

As of 27 Oct, 2026, prices found for a 1-night stay for 2 adults at Chesapeake Charm on 4 Nov, 2026 start from S$582, 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.

How much is parking at Chesapeake Charm?

On-site parking is available at the property.

What time is check-in at Chesapeake Charm?

Check-in begins at 4:00 PM.

What time is check-out at Chesapeake Charm?

Checkout is at 11:00 AM.

Where is Chesapeake Charm located?

Situated on the waterfront, this holiday home is within 1 mi (2 km) of Saint Jerome Beach and Chesapeake Bay. First District Community Park and Cardinal Gibbons Park are also within 9 miles (15 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. 101 out of 109 reviews
Rating 8 - Good. 5 out of 109 reviews
Rating 6 - Okay. 2 out of 109 reviews
Rating 4 - Poor. 0 out of 109 reviews
Rating 2 - Terrible. 1 out of 109 reviews

9.4/10

Cleanliness

10/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very charming, comfortable house and beautiful property, wish we could have stayed longer.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A very comfortable place my friends and I wanted more time, beautiful to set a lot of blue crab to cook at the moment without a doubt we plan to return to this place now, if you want quiet space and good view this place is 10 /10
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice house. Host is attentive to our request. Caught many crabs, kids and puppy had a lot of fun ! Will come back!
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very comfortable in extreme heat. Our family reunion went great!
Stayed 6 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We rented this property because it was conveniently located for a day trip we booked with Desperate Measures guide service, and we really enjoyed everything about it. The nicely decorated interior gets wonderful light, and the furniture and beds are comfortable. The front and back porches are great, but if it rains the double garage doors make the garage a fantastic sheltered area to hang out. The dock was the perfect spot to watch the sun go down. The area is remote, which is perfect if you’re looking for peace and quiet. Next time we’ll stay longer than just a weekend!
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean house with plenty of seclusion. We had a great time crabbing and fishing from the private pier.
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at Chesapeake Charm. The location is great with picturesque views, fantastic sunsets, and a great place to get away from it all. The kitchen is large and well stocked. The living room is very comfortable, with lovely views of the woods. The bedrooms are spacious with comfortable beds. We have stayed in a lot of vacation rentals and this was by far the nicest. We highly recommend it, and look forward to visiting again. Thank you for a great stay!
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

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

Peaceful getaway

We had a great stay. The house was very clean and as advertised in photos. We loved the quiet outdoor space and use of the kayaks and dock!
Stayed 3 nights in Mar 2024
Verified review

10/10 Excellent

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

St. Mary’s College weekend

Great place for visiting St. Marty’s College for the weekend. Could see this being really nice for warmer weather days with the pier, kayaks, and big yard too
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

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

July 4th

Another great stay. Hope to come back again next year.
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was an amazing experience. The spot is beautiful - the kids loved kayaking fishing and crabbing, and the adults loved sitting out under the big shade tree and having conversation. We also went on a charter with the property owner, which was a terrific experience and I highly recommend.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

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

Relax

Absolutely a wonderful place to relax. So peaceful and beautiful. So much wildlife to enjoy. We will be back.
Stayed 3 nights in Jun 2025
Verified review

10/10 Excellent

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

Beautiful spot by the water

Nice secluded getaway right on the water. Exactly what we needed.
Stayed 2 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a wonderful time staying at Chesapeake Charm! The house was warm and inviting and exceptionally peaceful. The water was so relaxing and the sunset was amazing. Also recommend having a try at star gazing. We were able to see the Milky Way. Phil was a gracious host and provided check-in information promptly. Would stay again!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

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

Fourth Family Reunion

Stay was better than we expected. Very comfortable home and beautiful views. Hope to book for full week next 4th.
Stayed 4 nights in Jul 2023
Archival

10/10 Excellent

Heaven touches Earth.

Beautiful piece of property on the water. Home is lovingly cared for. Special attention given to details to make your stay enjoyable.
Response from VrboOwner on 3 Apr, 2020
So glad you guys were able to fully enjoy the property and getting out on the water!
Verified review

10/10 Excellent

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

Nice view

Beautiful view, house was clean. Looked like the pictures. We will atay again. Dogs enjoyed it there.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

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

Nice & quiet

It was a great way to spend a long weekend to get away from it all. But close enough to go out and pick things up without it being a bit to do.
Stayed 3 nights in Feb 2021
Response from VrboOwner on 22 Mar, 2021
Glad you enjoyed it! Being a little bit away, yet close enough - is favorite for many folks. Thank you.
Verified review

10/10 Excellent

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

Spring break

Easy check in. Kitchen was well stocked even with a welcome basket. Love that the garage door opened to the backyard and water view. There was plenty of wood for firepit.
Stayed 3 nights in Apr 2025
Archival

10/10 Excellent

Cookies and Milk!

Great place for families. Arrived to find much appreciated cookies and milk. House spacious and comfortable. View of Bay just as beautiful as pictured. Most special were the outdoor games and enormous lawn for playing.
Response from VrboOwner on 3 Apr, 2020
Thank you - our goal is to provide a clean, relaxing, "just like home" get-away for everyone. Glad you enjoyed your stay!
Verified review

10/10 Excellent

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

Perfect getaway for rest and relaxation.

Beautiful location with amazing sunsets. Rural setting yet close to attractions and necessities. House is cozy and comfortable and had everything we needed. Lots of wildlife around (deer, rabbits, eagles, water fowl, owls) and large yard perfect for lawn games. Just wish we could have caught some crabs off the pier- may have been too cold and late in the season though.
Stayed 4 nights in Nov 2020
Response from VrboOwner on 15 Mar, 2021
Thanks so much for the review; and we agree - the sunsets are amazing. If you ever make it back this way in the summer, you'll definitely enjoy some crabs.
Verified review

10/10 Excellent

Peaceful, clean and comfortable

Chesapeake Charm has all that you need for a restful getaway. The house is very clean, comfortable and well equipped. Snacks and drinks in the kitchen make a welcoming arrival. Very cosy during the cold weather this week. Great spaces outside to sit quietly, enjoy conversation and have fun. This little place is a gem right by the water.
Stayed 3 nights in Dec 2017
Response from VrboOwner on 3 Apr, 2020
Glad you enjoyed your stay and that you were able to enjoy cozy comfort in c o l d weather. We are blessed with 4 seasons - and the Chesapeake Charm seems to make the best of each of them.
Verified review

10/10 Excellent

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

Quiet and Comfy

We came down for a swim meet at St. Marys College and wanted to be somewhere more relaxing than a hotel. This property was perfect. It was super clean and the kitchen was stocked so I was able to cook healthy meals for the family every day instead of having to eat out. My son wants to come back when its warmer so he can fish.
Stayed 4 nights in Feb 2024
Verified review

6/10 Okay

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

Cute place

Overall the place was nice. Cute house with beautiful views. Only complaint were the beds, specifically the twin beds. We were there for a swim meet and the athletes really needed sleep. The teens said the beds were so hard and uncomfortable, they couldn't sleep. Luckily we brought an air mattress just in case.
Stayed 3 nights in Feb 2025
Verified review

10/10 Excellent

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

Beautiful remote property

We were at St. Mary’s for a swim meet. After being in a loud indoor pool all day, coming back to this quiet property with the soothing water was the reset we all needed. There were three generations of us and we all commented that we liked the place better each day— others have commented on how well-equipped the kitchen was (and it is) and the property was a delight for my 8 year old son, who explored just about every inch. Owners were super responsive and generous. Really loved this stay. Thanks!
Stayed 3 nights in Mar 2025
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