Entire home

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!

Reviews
10 out of 10 Exceptional
3 bedrooms2 bathroomsSleeps 10

Popular amenities

  • FireplaceFireplaceFireplace
  • Pet friendlyPet friendlyPet friendly
  • Outdoor SpaceOutdoor SpaceOutdoor Space
  • Free WiFiFree WiFiFree WiFi
  • Air conditioningAir conditioningAir conditioning
  • WasherWasherWasher

Check out the area

Map
Chestertown, MD
  • Popular LocationRiver Arts Chestertown5 min drive
  • Popular LocationWashington College6 min drive
  • Popular LocationRolphs Wharf Marina12 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 Twin Bunk Bed and 1 Queen Bed

Bedroom with river view

1 King Bed and 2 Twin 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
Onsite parties or group events are strictly prohibited
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 indicated there is a smoke detector on the property

About the neighborhood

Chestertown

Located in Chestertown, this vacation home is in the city center 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. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Map
Chestertown, MD

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!?

Check-out is at 11:00 AM.

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

Located in Chestertown, this beachfront vacation home is in the city center, 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

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 59 out of 64 reviews" "
Rating 8 - Good. 5 out of 64 reviews" "
Rating 6 - Okay. 0 out of 64 reviews" "
Rating 4 - Poor. 0 out of 64 reviews" "
Rating 2 - Terrible. 0 out of 64 reviews" "

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Emily L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything you could want
Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
Stayed 3 nights in May 2023

10/10 Excellent

Michael F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Always a delight!
We have come to this wonderful get away on the Chester river again and again over the last 4 years. We never grow inured to its charms. For us the glorious sunsets, peaceful evenings, and avian visitations create a state of continuous wonder. We have fallen in love with the quiet peace of the place. Ina has always been a caring and responsive host. And Chestertown is a great source of indulgent provisions.
Stayed 7 nights in Mar 2024

10/10 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

10/10 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

10/10 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

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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