Chestertown Rentals USA Maryland Chestertown

Beautiful, spacious waterfront home, an easy walk to historic Chestertown | House in Chestertown

9.8 (22 Reviews) |   6 Bedrooms  6 Bathrooms  14 Guests  Stay&Play
Chestertown House | Beautiful, spacious waterfront home, an easy walk to historic Chestertown

6 Bedroom House in Chestertown

Welcome to Riverfront Retreat, a beautiful and spacious home where your family will be able to relax and enjoy the best of the Eastern Shore. With two main floor bedrooms, including a master suite accompanied with sitting room with full river views. The second main floor bedroom, our Library Bedroom, is spacious and features hardwood floors and built in bookcases. The four large bedrooms on the second floor provide plenty of room to spread out and enjoy. Two of the upstairs bedrooms have their own bathroom, and a jack-n-jill bathroom serves the other two bedrooms.
The main floor living areas are equally built to please - the 33X24 combination LR/DR with hardwood floors and a cathedral ceiling is a great spot for family meals around the 14 person dinner table, and for games, all while looking out at the river. Get closer to the river on the deck, which receives mid-day sun, as well as shade from the large Magnolia adjacent to our home.
The main floor kitchen is fully equipped with a large center island, breakfast dining area, and another set of breathtaking views of the river. The ground floor features a great room with pool table, 75 inch television, and views of the river.
Prefer to eat outside? The ground floor also includes a substantial screened-in-porch, complete with two ceiling fans, as well as a table with seating for eight that is ready for you.
Beyond the many attributes of the house itself, the property features a 110 foot private pier, which is great for launching the kayaks that are provided for your enjoyment (4 single, one double), the paddleboard, swimming, and there is a mooring at your disposal if you want to bring your power boat.
All of this, and you are about a four block walk to historic Chestertown.
We purchased the home in November 2020 from the original (1989) owners, and we love this place! In early 2021 the main entry, LR/DR, MBR, Library bedroom, and all upstairs bedrooms were freshly painted and updated. The furniture in the LR/DR and breakfast room is fresh too. Likewise, the furniture on the ground floor, in the great room and the screened-in porch is all fresh. The pool table in the ground floor great room is a classic, which we purchased from a Chestertown resident, and we had it re-felted in the spring of 2021.
The main floor, primary kitchen is spacious and has served us as a wonderful gathering place, and it has original appliances including an electric stove. The ground floor, secondary kitchen is smaller and functional.
Our home is in a wonderful residential neighborhood. Most of our neighbors live in Chestertown year-round. It is important to us to be good neighbors, and so we aim to rent our home to people who want to use it for relaxing, fun vacation getaways - people who will use our home the same way we do. We want and need to be sure that our renters respect our neighbors and avoid any disruptive behavior - things like loud music, other excessive noise, or bright lights, particularly after hours. Likewise, parking is limited to six vehicles, which need to be kept on one of the two driveways. If you are looking for a beautiful home in a great area, with plenty of fun things to do, please come to our River Retreat!

Beautiful, spacious waterfront home, an easy walk to historic Chestertown is located in Chestertown. Beautiful, spacious waterfront home, an easy walk to historic Chestertown provides accommodation, featuring Parking, Bedding/Linens, Wellness Facilities, among other amenities. This House features Parking, Bedding/Linens, Wellness Facilities, to make your stay a comfortable one.

Beautiful, spacious waterfront home, an easy walk to historic Chestertown has 6 Bedrooms , 6 Bathrooms, and max occupancy of 14 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
  • Ocean 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: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome. note from host: waterfront is a small sand beach, 100' from house.
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 note from host: larger events are welcome, at an additional charge 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

Sep 24, 2024 12:26:35 AM
Summary: Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!
David K. David K.
Aug 7, 2024 01:07:38 AM
Summary: We had a great time
Harold L. Harold L.
Jul 21, 2024 04:26:20 AM
Summary: The property was ideal for a family vacation. Despite the hot weather outside the property inside provided comfortable and spacious surroundings with a magnificent view of the river. It is close to the center of the town of Chesterfield with many shops, restaurants, and historical buildings within s short walking distance. The people of the town are most engaging-helping to make the stay memorable. A very special home in a very special place.
Thomas H. Thomas H.
Sep 8, 2023 11:00:23 AM
Summary: This is the second year we stayed there. We met with the agent to explain what we rented the home for. She agreed and we rented the property. This year, although she had my direct cell number, she left me a note on the island about everything she was disappointed in from the previous year—everything we discussed in person before renting the home. In addition, the first year, I spoke with her and shared some things that needed to be fixed in the home, and when we returned this year, none of the items but the ice maker were fixed.
Janise F. Janise F.
Sep 1, 2023 06:54:24 AM
Summary: The house was perfect for a multi-generational family reunion. The house was clean, and the kitchen, bedrooms and bathrooms had everything we needed for our stay. The property manager was very helpful and easy to contact with questions. We enjoyed the water and beach and walking to Chestertown.
Helen C. Helen C.
Aug 10, 2023 12:00:25 PM
Summary: The whole family enjoyed this beautiful house. We also enjoyed the convenience of the dock right outside the backyard. The short walk into town was also nice
sandra l. sandra l.
May 18, 2023 08:21:45 AM
Summary: This property is huge and has everything you need to enjoy a waterfront vacation. We stayed with a group that was in town for a wedding. A beautiful quiet neighborhood within walking distance to everything in charming Chestertown. It was also great to have access to the kayaks and get on the water! The house was very clean but could benefit from some repairs. The deck needs to be redone and wasn’t as nice as the rest of the house. Especially the deck railing which was unstable, so we kept the kids away from it. Quite a few windows were inoperable due to the visible foundation issues. Additional seating on the deck and in the yard, extra pillows and blankets would have been nice, but overall would recommend this lovely waterfront home!
Maggie E. Maggie E.
Aug 31, 2022 05:48:05 PM
Summary: The house was everything we could have hoped for. Great location, plenty of space, clean, and spectacular views. We've already booked it for next year!
Tony P. Tony P.
Aug 6, 2022 08:37:14 PM
Summary: Rental process was very easy
Michael K. Michael K.
Jul 21, 2022 03:51:34 PM
Summary: My family and I enjoyed our stay in Chestertown. It was 11 of us… 9 adults and 2 teenagers (13 &15). The house with all the gorgeous views were so relaxing and peaceful. The house was spotless. We did early morning walks throughout the town and stopped at Evergrain bakery for bread and cinnamon rolls. Some days we rode the bicycles and that was fun. Everything was easy to find and the property manager was very helpful. Lovely house, lovely town, lovely people and a lovely stay!
Marilyn O. Marilyn O.

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 $1,223 per night with includes Child Friendly, Laundry, Ocean View, Balcony/Terrace, Sports/Activities, Fireplace/Heating, Entertainment, Barbecue/Outdoor Cooking, Hot Tub, Air Conditioner, View, Security/Safety, Internet, Kitchen, TV, Parking, Bedding/Linens, Wellness Facilities 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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