House in Chestertown, MD

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Photo gallery for Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Exterior
Beach
Pool
Property grounds
Property grounds

Overview of Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

5 out of 5 Exceptional
3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • FireplaceFireplaceFireplace
  • Pet-friendlyPet-friendlyPet-friendly
  • Free WiFiFree WiFiFree WiFi
  • WasherWasherWasher
  • DryerDryerDryer
  • Air conditioningAir conditioningAir conditioning

Enjoy the area

Chestertown, MD
  • Popular LocationRiver Arts Chestertown5 min drive
  • Popular LocationWilmer Park5 min drive
  • Popular LocationWashington College6 min drive
  • AirportSalisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)101 min drive

Rooms & beds

3 bedrooms (sleeps 10)

Bedroom 2

1 Queen Bed

Bedroom 3

1 Single Bunk Bed and 1 Queen Bed

Bedroom with river view

1 King Bed and 2 Single Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub · Toilet · Shower only

Spaces

Porch or lanai
Kitchen
Outdoor play area
Garden

About this property

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire the wildlife, and dip into the water via our 200+ foot private beach. It's an ideal destination that you can enjoy for hours on end throughout the year. The home is also located just a short bike ride to Historic Chestertown, or you can even take one of our kayaks in while you enjoy the Chester River's rich wildlife.

Guests can also enjoy our pier where you can go crabbing and fishing, or dock your own shallow water boat and use the 8k lb boat lift. We also have a fire pit for you to make cozy fires by the water with plenty of wood for you to enjoy the beautiful evenings.

The three bedroom and two bathroom home features a master bedroom with French doors overlooking the river and a screened in porch to just hang out and watch life go by. The two common areas have plenty of glass doors with spectacular views of the 200+ feet of private shoreline. There is also a giant TV for movies and a foosball table for hours of fun.

Minutes from our slice of Heaven you will find Historic Chestertown, founded in 1706, where there is no lack of things to do. Dock the kayaks at Chestertown's public floating dock (or bike or drive over) and explore the brick sidewalks lined with shops, restaurants, art galleries and everything you would expect from a quaint small town. By the way, the whole town is VERY dog friendly!

Chestertown is also a magnet for traveling foodies. Known for its wealth of Chesapeake cousine, Chestertown is located on the upper Eastern Shore section of the Maryland Crab and Oyster Trail. Visiting the Chestertown Farmers and Artisans market (Saturday mornings), is a great way to acquaint yourself with the local farmers and artisans. For special dietary restrictions you have Figg's Ordinary, and entirely gluten-free cafe. For something stronger, head to Bad Alfred's, featuring house-made spirits, local craft beer and wood-fired pizzas. You can also find 89 Cannon on the river where you can enjoy tranquil water views while eating delicious seafood and other American style food.

About 20 minutes away, you can find Crow Vineyard. For four straight years, Crow has achieved Maryland Governor's Cup Medal status and gold status at international wine competitions. Also 20 minutes away is the Eastern Neck Island National Wildlife Refuge, which is a 2,285-acre island featuring all kinds of Mid-Atlantic plant and wildlife species. It also has the Duck Inn Trail, a hike that takes you through forests and marsh and arrives at a yet another gorgeous vista overlooking the Chester River.

With so many things to enjoy, book your experience today!

**Sheets are provided and beds made, but please bring towels**

Property manager

Ina Herrera

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed: dogs (limit 2 total)
Please do not allow your pets on the furniture.

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

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
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Safety features at this property include a smoke detector

About the area

Chestertown

Located in Chestertown, this holiday home is in the city centre and on the beach. Rolphs Wharf Marina and Rock Hall Harbor are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Betterton Beach and Elk Neck State Park. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

What's nearby

  • Historical Society of Kent County Maryland - 5 min drive
  • River Arts Chestertown - 5 min drive
  • Wilmer Park - 5 min drive
  • Washington College - 6 min drive
  • Rolphs Wharf Marina - 12 min drive

Getting around

  • Baltimore, MD (MTN-Martin State) - 106 min drive

Restaurants

  • McDonald's - 7 min drive
  • Procolino Pizza - 7 min drive
  • Dining Hall - 7 min drive
  • Luisas Cafe - 7 min drive
  • Uncle Charlie's Bistro - 6 min drive

Frequently asked questions

Is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! pet-friendly?

Yes, this property allows dogs (limit 2 total).

What time is check-in at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Check-in begins at 3:00 PM.

What time is check-out at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Checkout is at 11:00 AM.

Where is Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! located?

Located in Chestertown, this beachfront holiday home is in the city centre, 2.2 mi (3.5 km) from Washington College, and 2.2 mi (3.5 km) from River Arts Chestertown. Rolphs Wharf Marina is 4.9 mi (7.8 km) away.

Reviews

5

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 5 - Excellent. 58 out of 63 reviews" "
Rating 4 - Good. 5 out of 63 reviews" "
Rating 3 - Okay. 0 out of 63 reviews" "
Rating 2 - Poor. 0 out of 63 reviews" "
Rating 1 - Terrible. 0 out of 63 reviews" "

4.9/5

Cleanliness

5/5

Check-in

5/5

Communication

5/5

Location

5/5

Listing accuracy

Reviews

5/5 Excellent

Michael C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice house on a beautiful river front property
We had a fantastic get together with friends and family. Highly recommended.
Stayed 4 nights in Feb 2024

5/5 Excellent

Madeleine S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely Chestertown Getaway
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
Stayed 2 nights in Dec 2023

5/5 Excellent

Maria S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thanksgiving Retreat
Wonderful weekend with our daughters. Chester town was festive kicking off the holidays with a parade. This is our second trip to an area on the Eastern Shore and it did not disappoint. The home was lovely and a relaxing environment.
Stayed 2 nights in Nov 2023

4/5 Good

Debbie F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Not exactly as pictured
I have to start by saying that the property was not exactly as pictured. The pictures show a tidy uncluttered space inside and out, but that was not the case. The screened in porch was cluttered with too much furniture and other items. Some other spaces of the home were more cluttered than pictured as well. There were lights duct taped under the kitchen cabinets that were falling down. The exterior property maintenance could have been much better. For what we paid, we expected more. With all of this being said, it is a great house on the river that was clean on the interior when we arrived. There were six of us and we had plenty of room. We enjoyed our weekend despite the disappointment in some areas.
Stayed 3 nights in Sep 2023

5/5 Excellent

Karin C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Just what we were looking for
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
Stayed 3 nights in Sep 2023

About the host

Hosted by Ina Herrera

Host profile image
Being able to provide our renters with a place to relax and rejuvenate is our goal, the way it does for us when we visit with our own family.
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