See all properties
Entire home

Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing

Choose dates to view prices

Photo gallery for Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing

Exterior
Exterior
Fridge, microwave, oven, stovetop
Smart TV, fireplace, foosball
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms4 bathroomsSleeps 9

Popular amenities

  • Washer
  • Barbecue grill
  • Dryer
  • Fireplace
  • Kitchen

Explore the area

Map
Chester, MD
  • Matapeake State Park
    ‪10 min drive‬
  • Chesapeake Bay Bridge
    ‪15 min drive‬
  • Sandy Point State Park
    ‪18 min drive‬
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪53 min drive‬

Room options

About the neighborhood

Chester

This vacation home places you within a 10-minute drive of Chesapeake Exploration Center and Island Dog Park. The vacation home includes a kitchen, a fireplace, and a balcony.
View more Vacation Homes in ChesterOpens in a new window

What's nearby

  • Paul Reed Smith Guitars - 6 min drive - 3.5 miles
  • Matapeake State Park - 10 min drive - 5.8 miles
  • Chesapeake Bay Bridge - 15 min drive - 9.5 miles
  • Sandy Point State Park - 18 min drive - 11.4 miles
  • U.S. Naval Academy - 31 min drive - 20.5 miles

Getting around

  • Easton, MD (ESN-Easton - Newnam) - 31 min drive

Restaurants

  • ‪Chick-fil-A - ‬4 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Starbucks - ‬8 min drive
  • ‪Cracker Barrel - ‬8 min drive
  • ‪Pour House Pub - ‬6 min drive

About this property

Entire place

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

Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing

Enjoy waterfront views of Cox Creek from this stunning custom home on Maryland’s Eastern Shore. With its private pier, expansive outdoor spaces, and well-appointed interiors, this property is designed for ultimate comfort and relaxation.

Highlights:
Private waterfront pier for kayaking, fishing, and swimming
Outdoor living spaces: furnished sunroom, glass-railed deck, covered patio, and balconies
Luxurious master suite with spa bath, water views, and private balcony
Gourmet kitchen perfect for entertaining
Two recreation rooms with foosball, billiards, movie area, wet bar, and more

Sleeping Arrangements:
King En Suite Room (2nd floor): King bed, spa-like bathroom, private balcony, sleeps 2
Family Guest Room (2nd floor): Queen bed, Twin bed, shared full bath, sleeps 3
Main Floor Guest Room: King bed, shared full bath, sleeps 2
Lower Level Den: Full Murphy bed, full bath, sleeps 2

Amenities:
Gourmet kitchen with breakfast bar seating for 5
Multiple indoor/outdoor dining areas, including BBQ grill and fire pit
Game and entertainment space: billiards, foosball, board games, and a media room
Outdoor activities: 3 kayaks, hammock, enclosed outdoor shower, fire pit, grill
Tech-ready: High-speed internet, WiFi, flatscreen TVs
Convenient amenities: Washer/dryer, luxury linens, boutique-level toiletries
Pet-friendly: Dogs allowed with a $150 fee

Ideal For:
Families and groups looking for a waterfront retreat
Outdoor enthusiasts: boaters, kayakers, fishermen, cyclists, runners

Convenient access:
Downtown Annapolis: 25 minutes
Washington, DC: 45 miles
Baltimore: 46 miles

House Rules:
No smoking or parties
Must be 25+ to rent, with an adult present at all times
For your security, we have one door camera facing the outside of the home and a noise decibel monitor that is compliant with the law.
Check-in: 4:00 PM, Check-out: 11:00 AM
The vacation home is air-conditioned and features a kitchen, 4 bathrooms, and a balcony. There's space to spread out with 3 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

Property manager

iTrip Vacations Annapolis - Sean Degnan

Languages

English

Similar properties

Fridge, microwave, oven, stovetop

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
10.0 out of 10, Exceptional, 37 reviews
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room
  • Separate dining area

Entertainment

  • Games
  • Smart TV

Outdoor areas

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

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Foosball table
  • Kayak
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Winery tours 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

  • Garden

Policies

Check-in

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

Check-out

Check-out before 11:00 AM

Special check-in instructions

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

Pets

  • This property welcomes pets
  • Service animals exempt from fees

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 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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.

Property is also known as

12601

Frequently asked questions

What can I see close to this vacation home?

This vacation home is located in Chester, close to Matapeake State Park, Chesapeake Bay Environmental Center, and Love Point State Park. Paul Reed Smith Guitars is also within a driving distance of 4.3 mi.

Is parking available on site at this vacation home?

No, there isn't parking at this vacation home.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What amenities will couples enjoy at Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing?

Amenities that appeal to couples at this riverfront vacation home include a fireplace, a kitchen, and a smart TV.

Are there hot tubs at Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing?

No, there isn't a spa tub at this vacation home.

Does this vacation home include breakfast service?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay free of charge?

Although pets can't stay for free, they are welcome at this vacation home.

Does this vacation home have connecting rooms?

No, this vacation home doesn't feature connecting guestrooms.

How far is the airport from this vacation home?

The closest major airport to this vacation home is Easton, MD (ESN-Easton - Newnam), which is 24.2 mi away (31 minutes by car). Another top airport is Baltimore Washington Intl. Airport (BWI), which is around 25 mi away.

Can I book a room with a balcony at Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing?

Yes, every accommodation at Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing comes with a balcony with some featuring water views.

Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 26 out of 27 reviews
Rating 8 - Good. 0 out of 27 reviews
Rating 6 - Okay. 1 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Christine C.

Liked: Cleanliness

Perfect

Wish we could have stayed longer. Comfortable and very well equipped.
Stayed 2 nights in Jun 2025

10/10 Excellent

Lisa S., Virginia

Liked: Cleanliness
Stayed 2 nights in Apr 2025

10/10 Excellent

Daniel T.

Liked: Cleanliness

Perfect Get Away

The property was described accurately. The property was clean and functional. The environment was peaceful and we enjoyed our stay. We look forward to returning soon.
Stayed 3 nights in May 2025

10/10 Excellent

Elizabeth J.

Liked: Cleanliness

Lovely property

A Shore Thing was the perfect property for our long weekend trip! The only suggestion I can make to the owners is to replace the upstairs guest bedroom mattress- it’s sunken in the middle and was a bit uncomfortable for a couple sleeping in that room.
Stayed 2 nights in Mar 2025

10/10 Excellent

Bryce T.

Liked: Cleanliness

Good get away spot

Easy place to unwind, neighbors we a little closer than I had imagined from the listing but it was absolutely awesome location. Great eating options close by and great kitchen set up with plenty of room.
Stayed 3 nights in Feb 2025

10/10 Excellent

Barbara B., California

Liked: Cleanliness

Family wedding

We had an amazing time in Chester. The house was absolutely beautiful, So clean very, very, very well-maintained the kitchen was very well appointed. We all had a fabulous stay and look forward to another stay at this beautiful home. Thank you for making our trip so enjoyable.
Stayed 5 nights in Sep 2024

10/10 Excellent

John L., San Rafael, CA

Liked: Cleanliness

Amazing stay!

We had an incredible family reunion over Labor Day. Beautiful house and location. Took the kayaks out and caught some crabs on the dock! The game room and theater rooms were a hit with our teens. Would definitely stay again!
Stayed 4 nights in Aug 2024

10/10 Excellent

Erika S.

Liked: Cleanliness

Beautiful house in an excellent location!

We had a fantastic weekend celebrating with friends! 6 adults all fit comfortably in the house and had everything we needed. Being on the water was peaceful, no loud boats or jet skies. We would definitely stay here again!
Stayed 2 nights in Aug 2024

6/10 Okay

Joe H.

Stayed 3 nights in Jun 2024

10/10 Excellent

Harold W.

Liked: Cleanliness

Book it A Shore Thing is a sure thing

Fantastic views, super clean, well decorated with obvious thought put into the process. The management team was great. We made day trips into D.C., Baltimore for a baseball game, Annapolis, and Timonium for a horse auction. The afternoons and early evenings were perfect for relaxing on the balcony and enjoying the sunset. Convenient grocery stores if you need them, very good local restaurants. I highly recommend this property. It is among the best I have ever rented on VRBO. We had 6 adults in our party. Very spacious and all agreed the property was better than advertised. Travel times to the various places we visited were 30-45 minutes one way but that can stretch depending upon time of day and construction and security issued if you are going to D.C. I highly recommend this property and do plan to make a return trip.
Stayed 4 nights in May 2024

10/10 Excellent

Juliana S.

Liked: Cleanliness

The perfect home

The home and it's location were fantastic. Very clean and well-appointed. We enjoyed the layout and the space, and the view of the water was amazing in the Fall (kaledscope of colors)! Communication with the host was easy and prompt. Highly recommend and we will be back!
Stayed 2 nights in Nov 2023

10/10 Excellent

Michael S., Cherry Hill, NJ

Liked: Cleanliness

Great Experience

Driving through the relatively modest neighborhood before arriving at A Shore Thing was a bit misleading since once we arrived at the property it was everything that we were expecting. The outside of the house is handsome and the landscaping is beautiful. Inside the open first floor plan is spacious, bright, well-appointed with the large windows providing views from all over of the spectacular setting including beautiful sunsets. The basement offers another open area including a bedroom and a fabulous tv/movie viewing area with a huge hi-def tv. The second floor offers more open entertainment areas including a pool table, and the luxurious master suite with lovely water views and another bedroom. Aside from the master, the other bedrooms are modest, roomy enough but come with adjoining bathrooms which is a great feature. My biggest concern was the lack of a large neighborhood for a long walk without having to walk along the busy road for a block or so to get to where this was an extended neighborhood. However this is truly a wonderful place for a family gathering and we are planning on rebooking in the future.
Stayed 5 nights in Oct 2023

10/10 Excellent

Laurinda H.

Liked: Cleanliness

Great place to enjoy friends!

Everything was as advertised and better!! Five college friends and sorors celebrated 50 years of devoted friendship during a four-day stay. We had a blast! There is enough space, amenities, and wonderful views to make any stay memorable. While there is not a lot of entertainment in the area, there were plenty restaurants with great food. An outlet mall is 15 minutes away and Ocean City beaches are are an 1.5 hour day trip away. Perfect location and lodging for a quiet, low-key getaway. I highly recommend!!!
Stayed 4 nights in Sep 2023