Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town | House in Chestertown

9.8 (83 Reviews) |   Pet Friendly   3 Bedrooms  2 Bathrooms  6 Guests  Stay&Play
Chestertown House | Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

3 Bedroom House in Chestertown

Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining room, Deck, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 3 large bedrooms (3 queen beds + 2 twins.) Each bedroom has smart TVs. Two have views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa with air mattress & has a view of the river. The family room features hardwood flooring, wet bar w/wine frig, recessed lighting, smart TV, and decorative fireplace. The kitchen & dining area feature an open floor plan with ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are sliding glass doors from the dining area that will go out to a large deck that has a cushion patio set & umbrella. There is a laundry area that includes a stacked washer & dryer. All bathrooms have been renovated. There is a full living room with a view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. Bar-B-Que grill, (propane) as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available (pls note, although there are 4 adults life vests, we do not supply children's life vests. Although, we have young grandchildren & as long as they are not in use, feel free to borrow.) There is also a fire pit for those cool nights or to just hang out and make smoors. High speed internet added in 2021 NEW for 2022! The interior and exterior have been freshly painted. New siding and new living room furniture, new patio cushions, 6 smart tv's & ceiling fans. New for 2025! upstairs bedroom with walk in closet and private bath. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 25 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown.
** Some dates to consider for fun filled family weeks.
Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept
Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times. This whole area is loaded with festivals. Here's a few more.
Bettertown days @ Betterton Beach usually the fist weekend in Aug
The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & early Oct is Rock Hall's Fallfest.
Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. 3rd Thurs 6-8 pm is cars on high April thru Oct.
Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know.
Feel free to surf the web as well. Most of the local towns have event calendars you can find online.
Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. Neighbor has two dogs that are very friendly and may come over to greet you.
FYI, the school zone has camera 24/7, so watch your speed.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town is located in Chestertown. Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town provides accommodation, featuring Parking, Guest Services, Child Friendly, among other amenities. This House features Parking, Guest Services, Child Friendly, to make your stay a comfortable one.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town has 3 Bedrooms , 2 Bathrooms, and max occupancy of 6 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.

Show more
OneKey Logos

This Property is OneKey Eligible

Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.

JOIN TODAY

Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Guest Services
  • Entertainment
  • Breakfast
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
Read More Read Less

Policies

Check-in Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 25
Check-out Check-out before 10:00 am contactless check-out available
Child Policy Children are welcome.
Pet Policy 2 total (up to 50 lbs per pet) note from host: 4 pets weighting over 60lbs, please contact owner. pets allowed restrictions apply; for more information contact the property at the number on the booking confirmation service animals are welcome, and are exempt from fees
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 indicated there is a smoke detector on the property host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip onsite parties or group events are strictly prohibited safety features at this property include a fire extinguisher and a deadbolt lock 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

Nov 9, 2024 05:42:57 AM
Summary: Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts.
Sun P. Sun P.
Jun 24, 2024 03:37:54 AM
Summary: House was even better than the photos showed. We spent evenings out on the dock watvhing the river and beautiful views. The hosts thought of every detail for a perfect stay.
Sarah R. Sarah R.
Jun 19, 2024 08:46:16 PM
Summary: Loved the location next to the river. Spent a lot of time on the dock and in the yard. Proximity to Chestertown a real plus too. Great hosts!
Bob R. Bob R.
Oct 14, 2023 12:09:08 AM
Summary: We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!
Amber U. Amber U.
Sep 18, 2023 06:10:57 AM
Summary: Home was very clean and neat. We enjoyed the snacks, and little touches.
Allie P. Allie P.
Sep 2, 2023 09:21:48 PM
Summary: Very nice owner. Super helpful and dealt with our leaving stuff! Mailed the oops we left that so nicely. Cheers!
Catherine M. Catherine M.
Aug 20, 2023 08:07:37 PM
Summary: The property was awesome. We kayaked, kids enjoyed paddle boats, and relaxing by the water. The owners were excellent hosts. Chestertown farm market on saturday(s) is a must see. Dog friendly township. Will go back next summer.
Elamurugan S. Elamurugan S.
Aug 3, 2023 08:52:16 PM
Summary: We had a lovely stay at this cottage on the water. The cottage had its own dock, deck, mini beach, grassy yard with kayaks, paddle boat, stand up paddles —enough for everyone. The birding is brilliant. The hosts have created an environment that welcomes birds. On our morning paddle, we saw bald eagles, ample herons, other sea birds and an otter, snakes and turtles. The house has everything you need. It’s very comfortable with a full kitchen, games, plenty of different spaces to relax and enjoy your time with family. The hosts are super considerate and kind people. They know how to make a space that’s great for your holiday. Book now! You won’t regret it!
Maureen H. Maureen H.
Jul 10, 2023 05:34:13 AM
Summary: My wife and I and our 3 grandchildren had an absolutely fabulous time on the Chester River. The cottage accommodated us very well with a modern kitchen and 2tv spaces The dock offered a fishing spot and beautiful views. Our hosts, Dianna and Russ made the experience special by making sure the kids knew how to use the kayaks and where to swim and generally helping them enjoy themselves. A short ride to Rockhall for crabs and a fishing trip topped off a wonderful Eastern Shore Visit.
Bill F. Bill F.
Jul 6, 2023 08:39:44 PM
Summary: I picked this property out based on the listing description. My family and guests were skeptical coming into the weekend about what I had picked out! Everyone, from start to finish had a blast! We kayaked, threw fishing lines in the water. We offered to take the family to dinner the first night and they asked for burgers on the grill! We made s’mores. Watched fireworks from the pier. Played board games, watched movies. Went to a festival nearby. Had a few meals out at local spots. There were many special touches that could be pointed out. I have already shared with my friends. I hope to get back again. Unplug, relax, enjoy! Heaven.
Doris O. Doris O.

FAQ's

Is this Chestertown house pet-friendly for guests?

Yes, pets are 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 $515 per night with includes Child Friendly, Kitchen, Laundry, Air Conditioner, View, Ocean View, Security/Safety, Pet Friendly, Balcony/Terrace, Bedding/Linens, Wellness Facilities, Entertainment, Breakfast, TV, Oceanfront, Sports/Activities, Fireplace/Heating, Barbecue/Outdoor Cooking, Internet, Parking, Guest Services 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.

People Also Ask

Check House Availability
Nightly rates from:
US $515
You will be redirected to  
Hot Deal - It has been viewed 88 times today
Not the right fit? Check out our other properties in Chestertown
|
9.6 (19 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
5.0 (87 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Accessibility