Chestertown Rentals USA Maryland Chestertown

Breathtaking waterfront home on the Chester River | House in Chestertown

10.0 (35 Reviews) |   4 Bedrooms  4 Bathrooms  10 Guests  Stay&Play
Chestertown House | Breathtaking waterfront home on the Chester River

4 Bedroom House in Chestertown

Private, one-of-a-kind waterfront home on the Chester River minutes from historic Chestertown. Drive through a gated entry past your private pool and extensive landscaping to a spectacular vista sweeping the riverfront. Bring your own boat or simply enjoy the recently updated custom Ipe deck featuring pier and floating dock for easy access to the water.
Private beach with walk-in sandy river access is perfect for enjoying provided kayaks (1 adult and 2 child), stand-up paddleboards (2), life jackets included.
Enjoy your morning coffee from the expansive screened porch featuring 180-degree views of the beautiful Chester River. Amenities abound with a hot tub on the additional poolside deck, outdoor shower, provided pool floats, pool basketball and two adult bicycles (bring your own helmets).
The completely renovated and beautifully furnished home features a fully-equipped chef’s kitchen, bar seating and table for 8, sectional sofa and additional seating, bar height table, large screen TV, powder room and first floor master bedroom with magnificent en suite master bath and desk area.
Upstairs, there are three additional bedrooms (1 K, 1 Q) each with a private and updated full bath and access to a waterfront balcony that spans the home. The bunkroom features two sets of twin bunkbeds with trundles and includes gaming system, TV and comfortable kid-sized seating.
Take a short bike ride or walk into historic Chestertown to explore this quaint, historic town. Enjoy the farmer’s market every Saturday, speakeasy, cat café, whiskey distillery, River Packet boat cruise daily, wine and tapas bar, shops and multiple outstanding dining options. Check the town calendar and learn more at www.townofchestertown.com to schedule your visit to take advantage of the many special events held throughout the year. End your day gathered around the firepit to watch the blue herons and ospreys as the sun sets on another day in paradise.
Ask about discounted rates for extended stays.
Property information & notes:
- Swimming pool & hot tub open May 1-Oct. 1. Slide is not available for rental use.
- Ample parking for 3-4 vehicles
- First floor gas fireplace
- Gas Grill with provided propane
- Outdoor firepit
- Upstairs and downstairs full-size washer and dryer
- Freshly-laundered sheets & bath and beach towels are provided for your use
- Starter pack of shampoo, soap and toothpaste provided
- WiFi throughout property
- 4 TV’s with Apple TV and Firestick
- NO SMOKING INSIDE OR OUTSIDE ON THE PROPERTY – will result in immediate eviction
- NO PETS
- Please exercise caution when opening and closing the wall of sliding pocket doors. See instructions in welcome packet.
- Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property.
- Please respect the neighbors and neighborhood.

Breathtaking waterfront home on the Chester River is located in Chestertown. Breathtaking waterfront home on the Chester River provides accommodation, featuring Barbecue/Outdoor Cooking, Parking, Sports/Activities, among other amenities. This House features Barbecue/Outdoor Cooking, Parking, Sports/Activities, to make your stay a comfortable one.

Breathtaking waterfront home on the Chester River has 4 Bedrooms , 4 Bathrooms, and max occupancy of 10 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
  • Pool
  • TV
  • Private Pool
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Fireplace/Heating
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 3:00 pm contactless check-in available minimum check-in age: 25
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Smoking Policy Smoking is not permitted
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 long-term renters welcome 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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room 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

Apr 14, 2025 03:50:59 AM
Summary: The cool weather kept us indoors playing games, puzzles, drinking wine and eating great food we picked up at the farmers market. Took a while for the hot tub to heat up but it was wonderful.
kate k. kate k.
Jan 13, 2025 05:56:05 AM
Summary: We loved our stay as much as we did last year. We were there for 5 nights and celebrated Christmas with friends and extended family. The views from every room were spectacular. From breakfast to midnight snacks we enjoyed the river and the cozy stove while watching Christmas classics and playing all the games Santa brought us.
Sheila C. Sheila C.
Jan 1, 2025 07:50:47 AM
Summary: The house is beautiful, with a glorious glassed-in porch perched over the river. Ideal space for a family reunion. You couldn't ask for a better place on the river.
jacob s. jacob s.
Dec 2, 2024 04:59:27 AM
Summary: We can’t overstate what a great find this was. In addition to the lovely setting, the cottage was well equipped, the kitchen but also with games, art and craft supplies and puzzles for kids. We think in summer with the pool and river to enjoy it would be even better. We are grateful to the owners for being willing to share this treasure!
Margaret B. Margaret B.
Nov 5, 2024 03:16:07 AM
Summary: Great place and great stay!
JAMES C. JAMES C.
Nov 1, 2024 07:15:37 PM
Summary: We had an incredible stay at the house. The views from every room in the house were stunning . Stayed with family ages 3 to 89 and everyone was comfortable. Kitchen was wonderful and had everything you would need to cook and in perfect shape.We enjoyed being able to bring our boat and tie up to the dock. Chestertown is a mile away and has much to offer with wonderful shops and restaurants. Can’t wait to go back.
karin b. karin b.
Oct 25, 2024 06:44:25 AM
Summary: A very comfortable, very clean and family-friendly place. The amenities were great. Area is quiet. Beautiful view of the sunrise.
Richard A. Richard A.
Aug 6, 2024 11:14:03 PM
Summary: Great house. Perfect location. Wonderful host.
Christine C. Christine C.
Jul 29, 2024 09:36:12 PM
Summary: The house and property more than lived up to our expectations. We enjoyed floating the day away in the pool and kayaking in the morning. The kitchen had everything we needed to make dinner at night and the living room and screened in porch were comfortable to read and relax in the evening. Our family is already talking about coming back!
Michelle W. Michelle W.
Jul 17, 2024 10:02:17 PM
Summary: We were delighted with this lovely home! Family of 9 had a super time (age range 4-62). Amazing water views from every space on the river side of the house. Peaceful and quiet, we enjoyed watching the different birds, the sunrises and the interesting boats and water activities especially from the large screened porch room. We also enjoyed paddle boarding and kayaking on the river and swimming in the wonderful pool! We loved the thoughtful design and layout of the downstairs common areas. It was perfect for playing games, chatting and eating together as a family, but also having enough space to do individual things and still be together. Thank you so much for making this lovely home available! We will definitely be returning!
Kimberly D. Kimberly D.

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?

Yes, this Chestertown house has 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 $764 per night with includes TV, Balcony/Terrace, Security/Safety, Barbecue/Outdoor Cooking, Parking, Sports/Activities, Laundry, Private Pool, Bedding/Linens, Child Friendly, Air Conditioner, Pool, Fireplace/Heating, Internet, 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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