Chestertown Rentals USA Maryland Chestertown

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown | House in Chestertown

10.0 (102 Reviews) |   4 Bedrooms  3 Bathrooms  8 Guests
Chestertown House | Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown

4 Bedroom House in Chestertown

My place is located in a quaint neighborhood close to downtown Chestertown; 1 mile walk. This home has a large screened porch & inviting outside patio. Cruise the Chester River with the canoe or two paddle boards provided. Feel free to bring your boat & dock at our deep water pier. Crabbing* (trap & net), fishing (2 rods), & biking (4 provided) are also fun activities to enjoy here at the property. Fire pit (all seasons), indoor fireplace, and outdoor hot tub (available October through the end of April). We will do our best to keep hot tub in working order, but cannot guarantee it will be in working condition 100% of the time. It does take longer to get technicians out here. However we will do our best. We look forward to your stay. All are welcome.
*Crabbing is not as plentiful as years past, and only during the hot summer and early autumn.

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown is located in Chestertown. Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown provides accommodation, featuring Air Conditioner, Sports/Activities, Fireplace/Heating, among other amenities. This House features Air Conditioner, Sports/Activities, Fireplace/Heating, to make your stay a comfortable one.

Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown has 4 Bedrooms , 3 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Chestertown has interesting places to visit. If you want to learn more about the House in Chestertown, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • TV
  • View
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Hot Tub
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Check-in Check-in time starts at 4:00 pm minimum check-in age: 30
Check-out Check-out before 12:00 pm
Child Policy Children are welcome.
Pet Policy Pets not allowed
Other Policy 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 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 onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation
 
Chestertown, 21620, United States

What Our Guests say 500 + Reviews

Mar 26, 2025 07:05:06 AM
Summary: Beautiful views of the water. Amazing brand new hot tub. Very spacious layout of the house.
Molly J. Molly J.
Mar 17, 2025 10:48:04 AM
Summary: This property was absolutely perfect for our girl’s weekend. The location was convenient to town but still felt very private with a picturesque view of the river. The house was beautifully furnished, sparkling clean, and well appointed. We truly felt like a guest in someone’s home. We would love to stay again!
Karen F. Karen F.
Nov 4, 2024 02:13:30 AM
Summary: House was impeccable. Perfect location within walking distance to downtown Chestertown. Beth, the owner, was responsive and tended to our needs immediately. Highly recommend this beautiful, friendly home.
David C. David C.
Oct 24, 2024 09:40:46 PM
Summary: House was spotless and well appointed and as represented in the ad. Had a family gathering in town so didn't get to spend as much time at the house as we would have liked. Good communication with owner. Recommended.
Tim S. Tim S.
Sep 23, 2024 02:31:24 AM
Summary: This wonderful home sits right on the Chester River with a generous back yard and a dock. We kayaked and SUPed on the Chester River and thoroughly enjoyed our stay. Just over the bridge from Chestertown so easy access to shops, coffee, etc.
kirk d. kirk d.
Sep 12, 2024 01:00:34 AM
Summary: The property was very nice. Perfect for our group attending a wedding.
Patricia C. Patricia C.
Sep 3, 2024 08:15:36 PM
Summary: This house is perfect for a large family, with room for mom, dad, and at least four kids. That's not even counting couch sleepers. The property is exactly what you'd expect on the river with a nice long dock for fishing and crabbing, a spacious screened-in porch, and wonderful view of the sunset. The neighbors are great. They even brought us over some crab balls, which were delicious. Will definitely stay here again.
Gary W. Gary W.
Aug 19, 2024 08:33:37 AM
Summary: We had a great family vacation at this property … again The home and grounds are a good fit for a wonderful stay on the Chester River. And the property owner is welcoming and responsive.Thank you, Beth!
Irene M. Irene M.
Jun 27, 2024 06:42:54 AM
Summary: Spectacular, perfect calm, finely appointed - I just wish I realized I couldn't spend enough time there with my obligations and only-weekend schedule. Provided me late-night respite with a fabulous bed for a great night's sleep and morning shower, twice, leaving the five friends behind to follow later. We decidedly determined we'd have a reunion so we could just sit riverside and enjoy the gorgeous, hospitable property. Book it now!
Harriet S. Harriet S.
Jun 25, 2024 06:26:38 AM
Summary: We have stayed at various places in this area over the years and this one checked all the boxes.
Sara S. Sara S.

FAQ's

Is this Chestertown house pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chestertown house have a swimming pool?

No, this Chestertown house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chestertown house?

Best-rates for the Chestertown house starts from $583 per night with includes Parking, Balcony/Terrace, Bedding/Linens, Entertainment, Internet, TV, View, Security/Safety, Barbecue/Outdoor Cooking, Laundry, Air Conditioner, Sports/Activities, Fireplace/Heating, Child Friendly, Wellness Facilities, Hot Tub, Kitchen StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Chestertown house a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chestertown house wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chestertown house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chestertown house?

Based on the information reported by the owner or manager, the Chestertown house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chestertown house?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chestertown house are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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