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

4.9

Outstanding(73 Reviews)

House in Chesapeake Bay, NC

10 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

About this house rental

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**

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Dishwasher

Wheelchair accessible

Garden

Family friendly

Map of Chesapeake Bay, NC

Nearby attractions

Yorktown Battlefield

224.5 mi

American Revolution Museum at Yorktown

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

4.9

Outstanding(73 Reviews)

House in Chesapeake Bay, NC

10 guests · 3 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating

Free cancellationFull refund if you change your mind

Great for petsBring all your friends and family, even the furry ones

About this house rental

Amenities

Air conditioner

Pets allowed

Kitchen or Kitchenette

Internet / Wifi

Fireplace

Parking

Laundry

Dishwasher

Wheelchair accessible

Garden

Family friendly

Map of Chesapeake Bay, NC

Nearby attractions

Yorktown Battlefield

224.5 mi

American Revolution Museum at Yorktown

Reviews

4.9

Outstanding(73 Reviews)

4.9

Jun 2024

This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.

4.9

Jun 2024

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!!!

4.9

May 2024

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.

4.9

Apr 2024

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

4.9

Feb 2024

We had a fantastic get together with friends and family. Highly recommended.

4.9

Dec 2023

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!

4.9

Dec 2023

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.

4.9

Sep 2023

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.

4.9

Sep 2023

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.

4.9

Sep 2023

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.

4.9

Aug 2023

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!

4.9

Jul 2023

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.

4.9

Jul 2023

Great house, beautiful waterfront property!

4.9

Jun 2023

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. ❤️

4.9

May 2023

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

4.9

Apr 2023

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

4.9

Apr 2023

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.

4.9

Apr 2023

A great place to relax and enjoy the Chester river and surrounding area. Rental has all the amenities. Can’t wait to go back!

4.9

Apr 2023

Great place! Would love to stay in the summer when the weather is warmer and enjoy the outdoors. Enjoyed our time there with visiting with family.

4.9

Mar 2023

The illuminated pier at night was a treat!

4.9

Mar 2023

Our stay was short, but absolutely fantastic! Great house, stunning view. We will definitely be back it must be even more gorgeous in the summer. ♥️

4.9

Jan 2023

Lovely setup on the water

4.9

Nov 2022

Perfect experience

4.9

Oct 2022

Despite having the remnants of hurricane Ien for 3 of the 4 days of our stay, the house was very comfortable with a great view of th Chester River.

4.9

Sep 2022

Can't say enough about this home. The location was great to town and from Baltimore. The house had just about everything you would need, and more. But the best of all was being outdoors on the dock, at the fire pit and on the water in a kayak. We hope to come back again.

4.9

Sep 2022

The property is a perfect family retreat. We were in the area, however, for a family wedding. We shared the property with six adults and an infant. The property was accurately depicted in the listing. I wished we had more time, in warmer weather, to take advantage of the river with the available toys (kayaks, paddle boards, and bikes) at our disposal. The owners were responsive and readily available for questions before and during our stay. The nearby town was quaint and historic. I highly recommend this property if you plan to be in the area.

4.9

Sep 2022

The property was exceptionally well-appointed, from the kitchen equipment to the outdoor equipment (kayaks. paddle boards, bikes, etc.). We enjoyed the firepit by the water and used the dock for some very successful fishing! We will be back for sure :)

4.9

Aug 2022

My family and I enjoyed a few days of relaxation while we watched the water, some boaters, and wildlife through the many glass doors (we had a very hot few days). We were also able to enjoy the kayak and fire pit. The home was clean and spacious. There are plenty of areas to spread out or gather together for games. We enjoyed our stay.

4.9

Aug 2022

The property is beautiful with lots of toys (paddleboards, kayaks, etc.) for guests to use. The house was very clean. Everyone in my family enjoyed our stay here.

4.9

Aug 2022

Stayed here for 3 nights with our extended family (six adults, one toddler, one infant, and dog). We were very comfortable and appreciated the layout of the house as it allowed us to keep our family with young children somewhat separated from the noise when they went to bed before the others. Our daughter swam in the river everyday (definitely bring water shoes at it is very rocky in the water and some glass washes up on the beach) and played with her sand toys. Our dog ran freely without worrying about traffic since the house is set back. We loved using the fire pit and fishing off the docks. Grocery store and anything you could need just a few miles away. This is a little gem, a perfect place to escape from the busy world and make memories.

4.9

Jul 2022

Summer Vacation

Summer Vacation

We had a great family trip. The location is perfect and was very peaceful. The house had lots of games for kids and was very comfortable. We will stay again.

4.9

Jul 2022

Relax

Relax

Property had a terrific outdoor set up and view!!

4.9

Jun 2022

June wedding weekend

June wedding weekend

A seamless experience from start to finish. We were pleased with the space and amenities.

4.9

Jun 2022

My best friend and I had a great time at this beautiful house! The interior is lovely, with plenty of open space and an awesome foosball table. : ) The back yard, pier and fire pit are a fantastic place to relax - as is the screened-in porch, where we spent most of our time. Many thanks to Ina and Mynor!

4.9

Jun 2022

We went for a family getaway. Beautiful property and views of the river. We watched the eagle in the morning and deer in the evening. Quiet and relaxing.

4.9

Jun 2022

Beautiful house by the river

Beautiful house by the river

4.9

Jun 2022

Beautiful setting

Beautiful setting

We went for a family getaway. Beautiful property and views of the river. We watched the eagle in the morning and deer in the evening. Quiet and relaxing.

4.9

May 2022

House is beautiful!

House is beautiful!

Beautiful home w an amazing river view- house has everything you need and more. Highly recommend!

4.9

Apr 2022

Clean and staged to perfection. Although we were here in March and it was way too cold and windy to use all the "toys" (i.e. kayaks, standup paddle, screened in porch, outdoor fire pit), we thoroughly enjoyed the fireplace (there are two) and great places to read a book or converse, and play games. The location is so close to downtown Chestertown with its great restaurants and wonderful farmers market. There was great biking in Eastern Neck National Wildlife Refuge (we used our bikes but there are bikes available as well). We highly recommend this place as a get away for families or couples.

4.9

Mar 2022

Excellent house with a fantastic view

Excellent house with a fantastic view

FAQs

How much does this house cost compared to others in Chesapeake Bay?

The average price for a rental in Chesapeake Bay is £211 per night. This rental is £165 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

We found 12 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.

Explore similar vacation rentals in Chesapeake Bay

Explore all rentals in Chesapeake Bay

Start earning One Key rewards

4.9

Outstanding(177 Reviews)

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

House

in Ridge

10 guests · 3 bedrooms · 3 baths

Garden · Pets allowed · Kitchen or Kitchenette

The best choice in Chesapeake Bay for House, for £305 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

££££

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

House in Chesapeake Bay, NC

Reasons to book

About this house rental

Amenities

Map of Chesapeake Bay, NC

Nearby attractions

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

House in Chesapeake Bay, NC

Reasons to book

About this house rental

Amenities

Map of Chesapeake Bay, NC

Nearby attractions

Reviews

FAQs

How much does this house cost compared to others in Chesapeake Bay?

Is parking included with this house?

Is there a pool at this house?

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

What amenities are available at Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!?

Explore similar vacation rentals in Chesapeake Bay

Chesapeake Bay travel inspiration

Related vacation destinations