Waterfront 3bed/2.5 bath w/dock&beach close 2 town

Entire home in Chestertown, Maryland

  1. 8 guests
  2. 3 bedrooms
  3. 6 beds
  4. 2.5 baths
Hosted by Dianna
  1. 9 years hosting

Listing highlights

Self check-in

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Unbeatable location

100% of guests in the past year gave this location a 5-star rating.

Wake up to breakfast and coffee

Included essentials make mornings extra easy.
"Chester River Dreams" is a waterfront property located less than 5 mi to the center of town. There is a dock and “L” head to sit and relax, and a small beach area. A nice deck, fire pit, & kayaks and paddle boards to use. The property has high speed internet and smart TVs in the living room and family room & all bedrooms. New for 2025, the upstairs was renovated to include a queen , 2 twins, walk in closet, and full bath. We also added an office area to front bedroom.

The space
Everyone staying longer than 7 days, must sign a lease and rental rules before staying in our house. We do allow up to 2 pets, there is a separate agreement for them that you must fill out. There is a gas grill outside & plenty of seating. The fireplace inside is strictly for decoration, but there is firewood on the side of the house to use in the fire pit outside. PAC n play, monitor & highchair is also on site. Kayaks & paddleboards are available with adult life preservers only. (Do not leave near the water. They have been known to float away.) Adult life preservers are at the property. Smaller sizes may be available upon request. Please put away kayaks, paddleboards , paddles, cushions & umbrella and any chairs, before checking out. Please make note: There are no barriers between the properties and neighbor pets could visit. They are friendly.

Guest access
You have access to the whole house and all the exterior property including the deck, dock and small beach. I will contact you prior to check in with the entry code. There is plenty of parking for up to 4 cars. The neighborhood is secluded & quiet. Please make note: THERE NO FENSES BETWEEN THE PROERTIES IN THIS NEIGHBORHOOD AND NEIGHBORS DO HAVE PETS. They are friendly, but could wonder onto the property.

Other things to note
There is a 2 night minimum except for ALL holidays & special weekends. Then it is a 3 night minimum. NO SATURDAY Check-ins for 7 nights or longer. All guests exceeded 7 night stay, must sign a lease and rental rules prior to stay. We allow up to 2 pets up to 60 lbs each (contact for exceptions) a separate document applies. Beach towels are provided. You may not use bath towels on the beach or to dry wet pets. No pets on the furniture, No wet pets inside the house. Smoking is permitted outside as long as precautions are made to make sure smoke does not enter the property. Linens are included, but beds are not made up for sanitary reasons, unless requested in advance. Fireplace in the house is decoration only!

Where you’ll sleep

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What this place offers

River view
Private beach access
Kitchen
Wifi
Free parking on premises
Unavailable: Carbon monoxide alarm

Accessibility features

This info was provided by the Host and reviewed by Airbnb.
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Rated 4.7 out of 5 from 37 reviews.

Guest favorite
This home is a guest favorite based on ratings, reviews, and reliability

Overall rating

  1. 5 stars, 73% of reviews
  2. 4 stars, 24% of reviews
  3. 3 stars, 3% of reviews
  4. 2 stars, 0% of reviews
  5. 1 stars, 0% of reviews

Rated 4.8 out of 5 stars for cleanliness

Rated 4.9 out of 5 stars for accuracy

Rated 5.0 out of 5 stars for check-in

Rated 5.0 out of 5 stars for communication

Rated 4.9 out of 5 stars for location

Rated 4.7 out of 5 stars for value

Guest reviews mention

Where you’ll be

Chestertown, Maryland, United States
This listing's location is verified.

Neighborhood highlights

Our neighborhood is located on a private street. Nice to walk around. Very quite. End of the road. Plenty of fishing or crabbing (depending on the season) off the dock. Everything you need if you should decide to just stay on the property.

Meet your host

Host
46 reviews
4.72 out of 5 average rating
9 years of hosting
Lives in Chestertown, Maryland
My Husband and I live on the Chester River in Chestertown, MD. We have been in this area 25 years now and we love the historic small town vibes. We started in the boating community and eventually bought property here. I currently own and operate a small community pottery studio where I teach (mostly home school children & adults) the craft. My husband & I have been in the real estate business for over 30 years. We currently own 3 vacation rentals called "Gracious Living Vacation Rentals." There are 3 in our portfolio: Chester River Dreams, Beachside Dreams, & Ocean Dreams. One is located in Chestertown and the other 2 in New Smyrna Beach. We fell in love with New Smyrna and it's beautiful beaches 20 years ago when we purchased a timeshare. Ever since then, we have been talking about buying a place there and we finally pulled the trigger and wound up buying 2. Both units are located on the no drive beach. One is a lovely 1 bed/1 bath with a bunk room that accommodates up to 5 guests. Our other unit is a larger direct ocean front unit 2/2 with office space. When we are not personally visiting the area, we enjoy allowing others to share our space. We love the beautiful beaches here as well as being close to Flagler Ave and Canal St. which is great for shopping and restaurants. It's also only 20 minutes from Daytona! The 3rd property is a house located in the historic town of Chestertown, Maryland.

Host details

Response rate: 100%
Responds within an hour
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Things to know

Cancellation policy
House rules
Check-in: 4:00 PM - 2:00 AM
Checkout before 10:00 AM
8 guests maximum
Safety & property
Nearby lake, river, other body of water
Carbon monoxide detector not required
Smoke alarm