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Chesapeake Charm

Waterfront holiday home with kitchen and patio

Photo gallery for Chesapeake Charm

Air view of creek opening to the Chesapeake Bay
Your home-away-from-home!
Lots of room to play!
Large country kitchen.
Double ovens, ceramic cooktop, dishwasher and microwave.

Reviews

9.8 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 91400 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Outdoor space

Explore the area

View in a map
Dameron, MD
  • Place, Saint Jerome Beach
    ‪19 min walk‬
  • Place, St. Mary's College of Maryland
    ‪15 min drive‬
  • Place, Patuxent River Naval Air Station
    ‪21 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

About this property

Chesapeake Charm

Not ready for summer to end? Extend it with a long weekend at the Chesapeake Charm! This creek side home has just what you need for a little extended summer'ish fun! Come soak up gorgeous fall sunsets and RELAX!

Ready to Get-Away - but not totally off the grid? This Cottage Living style home provides an excellent get-away weekend or summer retreat. Enjoy waterfront, country living in this 3 bedroom, 2 1/2 bath home with pier; located along St. Jerome’s Creek on a 15-acre crop farm in Southern Maryland. This quiet, rural treasure is just a short drive from shopping, restaurants, bowling, movies and more! [St. Jerome’s Creek connects to the Chesapeake Bay, making it easy access for boaters – you can bring your boat and tie up to the pier. ]
The house and area are “shore-side, country”; its location is premier for crabbing and fishing in the Chesapeake Bay. It is perfect for folks who enjoy fishing, crabbing, boating, paddle boarding, kayaking, wind-surfing, pedal boating, biking, wildlife/bird-watching, long walks, quiet sunsets, star gazing, peaceful sunrises, outdoor BBQs, relaxing in the sunshine, yard lounging, and/or simply chilling out.
This clean, comfortable, home has a fully equipped kitchen, washer and dryer, satellite TV, DVD/VCR, wood-burning fireplace, supplies for crabbing and fishing, a gas grill, and fire pit (just right for s’mores with the kids). Sleeping arrangements include: queen bed [master bedroom]; queen bed [bedroom 1]; 2 twin beds [bedroom 2]; queen sleep sofa and twin sleeper oversized chair [living room].
Seasonal options for fun include a county fair, wine festival, farm market, oyster festival, corn maze, ghost walk, Christmas village & lights, etc. Should you decide to wander about the area, you’ll find plenty of dining and shopping (including antiques). If history is your interest, Point Lookout State Park (a Civil War site) is just south and hosts miles of protected land suitable for biking, jogging, beach walking or enjoying nature. St. Mary’s City, the original capital of Maryland and Sotterly Mansion are also nearby. If you want a day trip, you may consider Annapolis, Baltimore, Washington DC or King’s Dominion!
This home is positioned so close to the Chesapeake Bay, that you won’t want to miss the opportunity to spend a day charter fishing or enjoying a late afternoon, sunset cruise – fall sunsets are FABULOUS! Let us know and we'll coordinate arrangements with Fish The Bay Charters, located just one farm over.
Geared for casual living, we're available to provide flexible arrangements to accommodate folks in town for weddings, graduations, fishing charters, and more. It’s just right for the family vacation or that quick get-away to recharge your batteries.

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Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
Small video library and board games.
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Events

No events allowed
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Pets

Pets allowed: dogs less than 23 kg per pet (limit one pet total)
Pets considered - please note if bringing a pet
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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
On-site 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 indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

We should mention

A car is required for transport to and from this property

About the area

Dameron

Located in Dameron, this holiday home is in a rural area and on the waterfront. The area's natural beauty can be seen at Saint Inigoes State Forest and Point Lookout State Park, while Historic St. Mary's City and Patuxent River Naval Air Museum are cultural highlights. Discover the area's water adventures with kayaking and waterskiing nearby, or enjoy the great outdoors with cycling and ecotours.
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Map
Dameron, MD

What's nearby

  • Saint Jerome Beach - 19 min walk - 1.6 km
  • St. Mary's College of Maryland - 15 min drive - 16.8 km
  • Point Lookout State Park - 18 min drive - 20.7 km
  • Patuxent River Naval Air Station - 21 min drive - 27.2 km
  • Calvert Cliffs State Park - 40 min drive - 47.9 km

Restaurants

  • ‪St. James Deli - ‬13 min drive
  • ‪Hacienda Los Guayabos - ‬14 min drive
  • ‪SALT Waterfront Kitchen - ‬16 min drive
  • ‪St. Inigoes General Store - ‬11 min drive
  • ‪The Pub - ‬18 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 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 mile (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. 93 out of 101 reviews
Rating 8 - Good. 5 out of 101 reviews
Rating 6 - Okay. 2 out of 101 reviews
Rating 4 - Poor. 0 out of 101 reviews
Rating 2 - Terrible. 1 out of 101 reviews

9.4/10

Cleanliness

10/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Jessica B.

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

10/10 Excellent

Donald P.

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

10/10 Excellent

jennifer a.

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

10/10 Excellent

Michael S.

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

10/10 Excellent

susan s.

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

10/10 Excellent

Alana R.

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

10/10 Excellent

Steven D.

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

10/10 Excellent

Kelly H.

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

10/10 Excellent

Chris B.

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

10/10 Excellent

Steven D.

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

10/10 Excellent

Laura F.

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
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Sherry R.

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.

10/10 Excellent

Racquel K.

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

10/10 Excellent

Jeanne C.

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
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Lee W., Pollock Pines, CA

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.

6/10 Okay

Michelle B.

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

10/10 Excellent

Rachel P.

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

10/10 Excellent

Sharon H.

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

10/10 Excellent

Alison K.

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

10/10 Excellent

Lydie K.

Perfect house to relax and amazing view

Our family really enjoyed our stay. The house is beautiful, with a lot of charm and the view is just amazing. The kids had a really good time riding the bikes or just playing outside (as did our dog), and we also enjoyed the kayaks. Stephanie and Phil are really easy to work with. This house is perfect with you want to relax and enjoy time with your family or friends. We'll be back soon! Lydie
Stayed 3 nights in Mar 2018
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Ashley R.

Wonderful place!

This was such a relaxing vacation spot. The house was spotless and very comfortable. We had such a good time hanging out on the pier, cooking on the grill, watching the wildlife, and kayaking. All of the things we needed (grill, kayaks, fishing rods, fire pit, etc.) were provided. We could have had fun without leaving the house at all. But, we did take our bikes to Point Lookout State Park and we also made a stop at Slack Winery. Such a beautiful area. We can't wait to go back to Chesapeake Charm!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Roger L.

Waterfront Retreat

If you enjoy water related activities in a tranquil setting then this is a must rental. We towed our boat from Ohio and launched it across the creek from the property. The dock easily accommodates boats of varying sizes. We were able to enjoy cruising around the picturesque creek which has easy access to the Bay. The crabbing was excellent and we had steamed crabs every night during our stay. Phil and Stephanie were very accommodating and the house was clean and well maintained. Every summer we rent waterfront homes in Maryland and I can honestly state that this was one of our best rentals.

10/10 Excellent

Michele U.

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

Rural on the water setting

My son is stationed at PAX and daughter lives in Virginia. My me my husband, father and German Shepard we live in Ohio. So for Christmas we all came together to celebrate. This place was perfect! Large enough for 6 people and all the kitchen supplies we would need to cook Christmas dinner. They even had a Christmas tree and a few decorations up. We will be back during the warm weather to enjoy the water,fishing and crabbing. Thanks Phil!
Stayed 5 nights in Dec 2022

10/10 Excellent

Jennifer D.

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

5 star anytime of year

Our family loved our trip to Phil's place! The house was so comfortable and the location more beautiful than pictures show. We loved sunsets on the dock, family fun on the huge lawn, including cornhole from the house and wiffle ball we brought. Plenty of wood for fires and extra touches like snacks and good coffee. My kids have demanded we come back sometime other than late December for fishing and crabbing and we plan to do so. But December sunsets and the full moon were all we needed for a great Covid-19 getaway. And the St. Mary's historic city and Point Lookout Civil War fort for my history-buff husband. EVERYONE loved it!
Stayed 3 nights in Dec 2020
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Aaron L.

Exceeded all expectations.

What a great long weekend. The house and property are maintained in great condition. The house has everything you need to feel at home. We were able to catch enough crabs for a couple good dinners. The kids had a great time hand-lining for crabs, kayaking, fishing, playing in the yard, etc. The end of the dock ended up being a great place to watch fireworks in every direction on the 4th. The garage was outfitted with a grill, some fishing tackle, a firepit, cornhole boards, and many other fun things to do. Phil and Stephanie obviously care about the guests' experience, and it really shows. We definitely plan to be back.

About the host

Hosted by Phil Langley

Host profile image
Phil and Stephanie are locals - born and raised in Southern Maryland. Phil is a coast guard approved, licensed charter boat captain who has worked as a commercial waterman. He has spent many years fishing, crabbing and oystering on the Chesapeake Bay. Their appreciation of country living on the Chesapeake watershed has prompted them to extend the Chesapeake Country experience to their fishing clients and others. Captain Phil is eager to share his knowledge - from catching fish to cookin' crabs!

Why they chose this property

When the neighboring farm (Phil's parent's home) became available in 2010, the weekly rental idea stepped closer to reality! This property is a compilation of waterfront, pier, large yard, corn/bean fields, and a comfy - well appointed home - complete with beautiful sunsets and tranquil mornings.

What makes this property unique

It's a wonderful place to experience shore-side, country living - fishing, crabbing, kayaking, sit-n-sip sunset cruises (right next door), or simply enjoying a gorgeous sunset at the pier. Looking for the right spot for your next summer vacation; Fall get-away; that special occasion, or holiday treat? Chesapeake Charm is just the spot! It's just right for a get-away with the girls, a long fishing weekend for the guys, a vacation with the family, a 'new' Thanksgiving tradition or a Christmas retreat - the possibilities are endless.

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