Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! - Queen Anne's County

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Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

3 bedrooms2 bathroomsSleeps 10

Popular amenities

Beach view

Hot tub

Washer

Outdoor space

Pet-friendly

Kitchen

Check-in time

3:00 PM

Check-out time

11:00 AM

Explore the area

Chestertown, MD

River Arts Chestertown5 min drive
Washington College6 min drive
Rolphs Wharf Marina12 min drive
Salisbury, 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

Languages

English, Norwegian, Spanish

Amenities

Hot tub

Kitchen

Washer

Dryer

Pet-friendly

Free WiFi

Kitchen

Washer

Dryer

Pet-friendly

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

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

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 that there is a smoke detector on the property

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 Eastern Neck National Wildlife Refuge. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Chestertown, MD

What's nearby

Historical Society of Kent County Maryland - 5 min drive
Garfield Center for the Arts at the Prince Theater - 5 min drive
River Arts Chestertown - 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 (3.6 km) from Washington College, and 4.9 mi (7.8 km) from Rolphs Wharf Marina. Betterton Beach and The Mainstay are also within 16 miles (25 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Cindy D.

3 June 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Place on the River in Chestertown

We really enjoyed our stay here. It was well appointed with kayaks and other outdoor activities, comfortable and beautiful views from the within the and the kitchen supplies were wonderful!! It is situated right on the river and we enjoyed our morning coffee at the end of the short pier. We are hoping to return!!!

Stayed 2 nights in May 2024

10/10 Excellent

Suzan B.

25 May 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relax, Recharge & Reconnect

This was the perfect place to gather our family of 5 adults and our 3 fur babies to celebrate Mother’s Day over the weekend. The house is beautifully decorated and we thoroughly enjoyed the large property that was very private and had not only access to the water but also stunning views. We look forward to coming back.

Stayed 2 nights in May 2024

10/10 Excellent

Bryn M.

22 Apr 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

Beautiful home and property! Host was very communicative and even gave suggestions for places to go in town. Would definitely book again.

Stayed 2 nights in Apr 2024

10/10 Excellent

Emily L.

12 Apr 2024

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.

30 Mar 2024

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.

26 Feb 2024

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.

30 Dec 2023

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.

12 Dec 2023

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

8/10 Good

Debbie F.

22 Sept 2023

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

10/10 Excellent

Karin C.

22 Sept 2023

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

10/10 Excellent

Adam B.

17 Sept 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding Weekend

Our adult family stayed for the weekend to attend a nearby wedding. Property is expansive with all the amenities that you can imagine. House is clean, well equipped and beautifully situated. I highly recommend.

Stayed 2 nights in Sep 2023

10/10 Excellent

Elyce R.

19 Aug 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Family Vacation in Chestertown

We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!

Stayed 7 nights in Aug 2023

10/10 Excellent

Michael F.

11 Aug 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

An escape to a peaceful river getaway

We have visited Ina’s house on the Chester river several times. It is a serene and peaceful sanctuary perfect for watching the birds and kayaking amongst the reedy shores. A stay here always serves to restore our souls.

Stayed 14 nights in Jul 2023

10/10 Excellent

Melanie B.

31 July 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway spot

My two young kids loved swimming in the river. One has sensory needs and enjoyed the muddy waters immensely. The house was nicely set up to give my family of four and my mother in law a little privacy in the evenings. Would recommend and come again. Communication with hosts easy and prompt.

Stayed 3 nights in Jul 2023

10/10 Excellent

Patricia D., Warrington, PA

23 July 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chestertown rental

Great house, beautiful waterfront property!

Stayed 7 nights in Jul 2023

10/10 Excellent

Crystal P.

22 June 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Place

This home was a lovely place to stay and relax. Very charming. Beautifully decorated but still comfortable. After 3 days in D.C., this was a great getaway. If we get back to the Maryland area, will likely stay here again if available. ❤️

Stayed 3 nights in Jun 2023

10/10 Excellent

Kathryn W.

30 May 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great weekend!

Thank you for sharing your wonderful home with us! Everything was perfect for our stay-we look forward to staying again soon!

Stayed 3 nights in May 2023

10/10 Excellent

kathy g.

23 Apr 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Get-Away

Beautiful property on the river . lots of amenities. Quick drive into quaint Chestertown

Stayed 4 nights in Apr 2023

10/10 Excellent

Michael F.

22 Apr 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another relaxing stay at this bucolic riverfront getaway

We have been back to Ina's beautiful house several times and each time is a pleasure. We enjoy the quiet, the birds, the river's ebbs and flows, and the spectacular sunsets.

Stayed 3 nights in Apr 2023