Skip to Main Content.
List your propertySupportTrips
Unlock instant savings with Member Prices
Sign in
Feedback
Entire home

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Riverside holiday home with kitchen and balcony

Photo gallery for Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Exterior
Smart TV
Property grounds
Fridge, microwave, oven, stovetop
Interior
Riverfront Retreat, a spacious home on the Eastern Shore, offers a relaxing getaway for families. With two main floor bedrooms and four upstairs bedrooms with private bathrooms, there's room to spread out. Enjoy meals in the combination living/dining room or outside on the deck overlooking the river.

Reviews

9.8 out of 10
Exceptional

Entire home

6 bedrooms6 bathroomsSleeps 14

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Barbecue grill
  • Outdoor space
  • Parking available

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

Riverside holiday home with kitchen and balcony
This smoke-free holiday home features laundry facilities, an arcade/games room and a garden. Other amenities include barbecues. The holiday home boasts a jetted bath and offers a kitchen and a washing machine. Guests can appreciate conveniences, such as 6 bathrooms and a dining area, and other amenities include a balcony and a Smart TV.
Air-conditioned accommodation at this holiday home offers a safe and coffee/tea makers. Rooms open to balconies. Kitchens offer fridges, stovetops, microwaves and separate dining areas.

Bathrooms include baths or showers with in-room jetted baths and hairdryers. Smart televisions are featured in guestrooms.

The recreational activities listed below are available either on-site or nearby; fees may apply.

Property amenities

Beach

  • Beach towels

Internet

  • Available in the house: WiFi

Parking and transport

  • Limited on-site parking (max 6 spaces)
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 6 private bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Ceiling fan
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Hardwood flooring in public areas
  • Smoke-free property

Services and conveniences

  • Phone
  • Safe

Location highlights

  • In the city centre
  • Near a hospital
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycles
  • Billiards/pool table
  • Kayak
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • Bicycles
  • Garden

Similar properties

Property grounds

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

  • Pool
  • Hot tub
  • Kitchen
  • Washer
10.0 out of 10, Exceptional, 13 reviews
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

Pets not allowed

Children and extra beds

Children are welcome
Note from host: Waterfront is a small sand beach, 100' from house.

Events

No events allowed
Larger events are welcome, at an additional charge

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
Note from host: Larger events are welcome, at an additional charge
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 not indicated whether there is a smoke detector on the property
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

About the area

Map
Chestertown, MD

What's nearby

  • Historical Society of Kent County Maryland - 6 min walk - 0.6 km
  • River Arts Chestertown - 8 min walk - 0.7 km
  • Washington College - 9 min walk - 0.8 km
  • Wilmer Park - 11 min walk - 1.0 km
  • Rolphs Wharf Marina - 12 min drive - 9.0 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 104 min drive

Restaurants

  • ‪Royal Farms - ‬5 min walk
  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin - ‬3 min drive
  • ‪Procolino's - ‬3 min drive
  • ‪Subway - ‬2 min drive

Frequently asked questions

Is Beautiful, spacious waterfront home, an easy walk to historic Chestertown pet-friendly?

No, pets are not allowed at this property.

How much is parking at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

Limited spots are available.

What time is check-in at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

Check-in begins at 4:00 PM.

What time is check-out at Beautiful, spacious waterfront home, an easy walk to historic Chestertown?

Checkout is at 10:00 AM.

Where is Beautiful, spacious waterfront home, an easy walk to historic Chestertown located?

Located in the heart of Chestertown, this holiday home is within a 10-minute walk of Historical Society of Kent County Maryland, Chestertown Historic District and Garfield Center for the Arts at the Prince Theater. Washington College and Sumner Hall are also within 10 minutes.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Beautiful, spacious waterfront home, an easy walk to historic Chestertown Reviews

9.8

Exceptional

9.6

Cleanliness

9.8

Location
Rating 10 - Excellent. 20 out of 23 reviews
Rating 8 - Good. 3 out of 23 reviews
Rating 6 - Okay. 0 out of 23 reviews
Rating 4 - Poor. 0 out of 23 reviews
Rating 2 - Terrible. 0 out of 23 reviews

Reviews

10/10 Excellent

Helen C.

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

Family reunion

The house was perfect for a multi-generational family reunion. The house was clean, and the kitchen, bedrooms and bathrooms had everything we needed for our stay. The property manager was very helpful and easy to contact with questions. We enjoyed the water and beach and walking to Chestertown.
Stayed 21 nights in Jul 2023

8/10 Good

Janise F.

Liked: Check-in, location, listing accuracy
Disliked: Communication

Bridgeway Community Church

This is the second year we stayed there. We met with the agent to explain what we rented the home for. She agreed and we rented the property. This year, although she had my direct cell number, she left me a note on the island about everything she was disappointed in from the previous year—everything we discussed in person before renting the home. In addition, the first year, I spoke with her and shared some things that needed to be fixed in the home, and when we returned this year, none of the items but the ice maker were fixed.
Stayed 6 nights in Aug 2023

10/10 Excellent

David K.

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

Awesome stay on the Chester River

Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!
Stayed 5 nights in Sep 2024

8/10 Good

Harold L.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Family Vacation

We had a great time
Stayed 5 nights in Aug 2024

10/10 Excellent

Thomas H.

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

Looking for the perfect getaway? This is it!

The property was ideal for a family vacation. Despite the hot weather outside the property inside provided comfortable and spacious surroundings with a magnificent view of the river. It is close to the center of the town of Chesterfield with many shops, restaurants, and historical buildings within s short walking distance. The people of the town are most engaging-helping to make the stay memorable. A very special home in a very special place.
Stayed 7 nights in Jul 2024

10/10 Excellent

sandra l.

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

Great House

The whole family enjoyed this beautiful house. We also enjoyed the convenience of the dock right outside the backyard. The short walk into town was also nice
Stayed 4 nights in Jul 2023

10/10 Excellent

Maggie E.

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

Great stay on the water for family and friends!

This property is huge and has everything you need to enjoy a waterfront vacation. We stayed with a group that was in town for a wedding. A beautiful quiet neighborhood within walking distance to everything in charming Chestertown. It was also great to have access to the kayaks and get on the water! The house was very clean but could benefit from some repairs. The deck needs to be redone and wasn’t as nice as the rest of the house. Especially the deck railing which was unstable, so we kept the kids away from it. Quite a few windows were inoperable due to the visible foundation issues. Additional seating on the deck and in the yard, extra pillows and blankets would have been nice, but overall would recommend this lovely waterfront home!
Stayed 4 nights in May 2023

10/10 Excellent

Tony P.

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

Excellent House!

The house was everything we could have hoped for. Great location, plenty of space, clean, and spectacular views. We've already booked it for next year!
Stayed 6 nights in Aug 2022

10/10 Excellent

Michael K.

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

Great house for a relaxing family and friends get-together

Rental process was very easy
Stayed 4 nights in Jul 2022

10/10 Excellent

Marilyn O.

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

Relax at River in Chestertown

My family and I enjoyed our stay in Chestertown. It was 11 of us… 9 adults and 2 teenagers (13 &15). The house with all the gorgeous views were so relaxing and peaceful. The house was spotless. We did early morning walks throughout the town and stopped at Evergrain bakery for bread and cinnamon rolls. Some days we rode the bicycles and that was fun. Everything was easy to find and the property manager was very helpful. Lovely house, lovely town, lovely people and a lovely stay!
Stayed 7 nights in Jul 2022

10/10 Excellent

Kate s.

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

Great place for a family gathering!

We’ll appointed and equipped house for a real Chester River experience. Access to the River and walkable to Chestertown makes this a special place to stay.
Stayed 4 nights in Jun 2022

8/10 Good

Ivonne R., Jacksonville, Florida

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

Family Wedding Weekend

We enjoyed the property very much. It is a spacious home with beautiful views and great backyard. It is an easy walk to the downtown in a very pretty neighborhood. The house fits many people and all the rooms are big and very comfortable. It was a fun time with my family!
Stayed 3 nights in Oct 2021

10/10 Excellent

Wayne C.

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

Great Weekend

Fantastic spot for a great weekend!!!
Stayed 3 nights in Sep 2021

10/10 Excellent

Tara R.

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

Wonderful Stay in Chestertown

We were a group of 3 families with kids ranging in age from 3 to 8. We had such a wonderful time at the River Retreat. The space is great for a large group, the "bunk room" perfect for kids who want to bunk together, and the river views, kayaks, and short walk to town make it perfect. Thank you!
Stayed 2 nights in Sep 2021

10/10 Excellent

Diane R.

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

Beautiful house and property

It is a very spacious beautiful house. Many indoor and outdoor toys to keep us entertained. Great responses when we needed to communicate. Lovely neighborhood and within walking to town. Only disappointment was how shallow the water at the dock was during low tide. We ended up renting a slip at the Chestertown marina which was close by so our boat trips were not limited by the tide.
Stayed 7 nights in Aug 2021

10/10 Excellent

Loren G.

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

Family Fun

Thanks so much for a wonderful home base for our extended family vacation. The house was perfect for us - clean, spacious, great location and management was easy to work with. We will be back!
Stayed 7 nights in Jul 2021

10/10 Excellent

john s.

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

Chestertown

My family and I thoroughly enjoyed our stay in Chestertown. The house is amazing and the views were breathtaking. It was nice to have the dock where we could keep our boat. We look forward to coming again in the future.
Stayed 6 nights in Jul 2021

10/10 Excellent

Lori J.

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

Chestertown's Best

The home was impressive with a lot of room for our multiple families to stay. Large kitchen, dinning and bedroom areas. We enjoyed the ability to take the Kayaks out on the water, walking downtown for ice cream and bake goods. We enjoy Chestertown with this being our second stay in the area. We will be back I am sure.
Stayed 7 nights in Jul 2021

10/10 Excellent

Sara S.

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

It was great, we had family members from age 3 to 83 and everyone enjoyed themselves.

So convenient would def recommend it.
Stayed 5 nights in Jun 2021

10/10 Excellent

Alyson O., Shelton, CT USA

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

Amazing Home

This home exceeded our expectations in every way. The property was exceptionally clean and well maintained. We enjoyed the water views and kayaks and exploring the nearby town on foot and on bikes. We rented the home for a special celebration and we are very happy with our stay.
Stayed 4 nights in Jun 2021

10/10 Excellent

Keith P.

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

Great long weekend stay!

Very cool house with all the amenities we needed for a great long weekend stay. Loved the view in the morning with coffee and house had so many areas to relax in. Screened porch in basement was really nice and loved the billiard room. It was also really cool that it is just a short walk to lots of shops and restaurants. There were several unexpected surprises like a firepit and commercial ice maker that were nice to have. Would definitely stay here again in the future.
Stayed 3 nights in Jun 2021

10/10 Excellent

Bethany C.

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

Perfect location, incredible home

Had an awesome weekend in the middle of winter with my husband. Can't wait to bring our whole family this summer. Highly recommend, definitely want to go back!