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Waterfront home with private pier and dog-friendly at A Shore Thing

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Come relax Eastern-Shore style at "A Shore Thing" on the water.
A Shore Thing sits on 1/2 acre of waterfront with a private pier.
Gather around the family room with gas fireplace and flat screen TV (behind closed cabinets).
The lower level den combines a theater room, living room, bar, bedroom and full bath.
Swim, kayak, crab or fish off the private pier, which extends out to Cox Creek.

Reviews

10 out of 10

Exceptional

3 bedrooms4 bathroomsSleeps 9

Popular amenities

  • Washer
    Washer
  • Barbecue grill
    Barbecue grill
  • Pet-friendly
    Pet-friendly
  • Parking available
    Parking available
  • Outdoor space
    Outdoor space
  • Kitchen
    Kitchen

Explore the area

Map
Chester, MD
  • Chesapeake Exploration Center
    6 min drive
  • Paul Reed Smith Guitars
    8 min drive
  • Love Point State Park
    13 min drive
  • Annapolis, MD (ANP-Lee)
    30 min drive

Rooms & beds

3 bedrooms (sleeps 9)

2nd Floor Guest room

1 Single Bed and 1 Queen Bed

2nd Floor Suite

1 King Bed

Lower Level Family Recreation Room

1 Double Bed

Main Floor Guest room

1 King Bed

4 bathrooms

Connecting Hall

Bathtub or shower · Toilet

King En Suite

Bathtub or shower · Toilet

Lower Level Recreation Room

Bathtub or shower · Toilet

Main Floor King

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Separate dining area
Outdoor play area
Garden
Dining Area

About this property

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
Check-in: 4:00 PM, Check-out: 11:00 AM

Property manager

iTrip Vacations Annapolis - Sean Degnan
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

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 not indicated whether there is a smoke detector on the property

About the area

Chester

Located in Chester, this holiday home is on the waterfront. Chase Lloyd House and Hammond-Harwood House are local landmarks, and the area's natural beauty can be seen at Matapeake State Park and Love Point State Park. Travelling with kids? Consider Paul Reed Smith Guitars, or check out an event or a game at Alumni Hall. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Chester, MD

What's nearby

  • Paul Reed Smith Guitars - 8 min drive
  • Matapeake State Park - 10 min drive
  • Chesapeake Bay Bridge - 17 min drive
  • Sandy Point State Park - 18 min drive
  • U.S. Naval Academy - 29 min drive

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

Frequently asked questions

Is Waterfront home with private pier and dog-friendly at A Shore Thing pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Waterfront home with private pier and dog-friendly at A Shore Thing?

Check-in begins at 4:00 PM.

What time is check-out at Waterfront home with private pier and dog-friendly at A Shore Thing?

Checkout is at 11:00 AM.

Where is Waterfront home with private pier and dog-friendly at A Shore Thing located?

Located on the waterfront, this family-friendly holiday home is within 6 mi (10 km) of Island Dog Park, Paul Reed Smith Guitars, and Chesapeake Exploration Center. Queenstown Premium Outlets and Matapeake State Park are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 21 reviews" "
Rating 8 - Good. 0 out of 21 reviews" "
Rating 6 - Okay. 1 out of 21 reviews" "
Rating 4 - Poor. 0 out of 21 reviews" "
Rating 2 - Terrible. 0 out of 21 reviews" "

9.6/10

Cleanliness

9.6/10

Check-in

9.0/10

Communication

9.4/10

Location

9.6/10

Listing accuracy

Reviews

10/10 Excellent

Barbara B.

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

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

Disliked: Communication
Stayed 3 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Wedding Weekend
The house is great. First floor is wide open which was perfect for hair and make-up for my daughter’s brides maids so that they could all be together in one room. Plenty of room on the upper and lower floors too so we weren’t tripping over each other. Back deck is great with an amazing sunset view too!

10/10 Excellent

Harold W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Christopher D.

Shore Place was as advertised
Super clean and well thought out property helped us on a quick two night getaway in early March. While it rained one day, the windows and loads of activities (pool table, theatre room, etc.), easily helped us pass the time. Will definitely be back!!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Ashley B.

Awesome house!
We loved our stay at It’s a Shore Thing! The house was clean and well stocked. The open floor plan was perfect for our girls get-away weekend. We didn’t want to leave, and we are already planning our trip next year. Loved this house!
Stayed 2 nights in Feb 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Candice

Most perfect view
I cant tell you all the fabulous things about this house. First off it’s pet friendly spacious with plenty of areas to relax and wind down. The views are breathtaking out each, and every window just sit on the dock of the bay and watch the ducks play and frolic in the water. Conveniently located to everything in a quiet and peaceful neighborhood. The interior of the home was beautiful and spotless 10 out of 10 would recommend. Can’t wait for our next stay!

10/10 Excellent

Juliana S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Elizabeth P.

Great place!
Nice big house, beautiful water access, lots of amenities, close to DC, everything you’d need in a rental, great place for a group. Very happy with our stay, my family thinks I’m a genius for finding this.

10/10 Excellent

Michael S., Cherry Hill, NJ

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Greg

Navy Game Get Away
Breath taking waterfront views makes this place a family favorite
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Tamara L., Sandy, Oregon

Great autumn stay.
We stayed for a week visiting family from Maryland. We needed a first floor bedroom/room and found the house fit our requirements. The outside deck was the best part and we spent mornings with coffee enjoying the crabbers on the river and evenings looking out on the sunset. We couldn’t figure out the roll out awnings but the two umbrellas were great for sun management. The deck fire pit was awesome. Shower stall floors were a bit slippery but itrip are aware. Kitchen was nicely stocked. Place was clean with plenty of bedding. Nice having the downstairs tv room. The Murphy bed is a tad soft but other beds comfortable. Neighborhood is very quiet. Lots of room to spread out for all of us. We went sightseeing around the island and down to St Michaels. We spent a couple days in DC (easy drive) and spent a day in Annapolis. BWI was an easy hour away. The kayaks were used but the water had a lot of jellyfish so no swimming. ITrip was very responsive with a couple of questions and needs. We had perfect warm fall days to enjoy Maryland. Will definitely stay in It’s a Shorething again.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Bj

Wonderful Stay
A ShoreThing was absolutely the best get-away ever! From the moment you want in a see that fantastic view you are drawn into the warmth of the home. This is one beautiful home with special touches all over. I will be back time and time again!

10/10 Excellent

Laurinda H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

annamarie l.

A Sure Thing
I stayed here with my family in August and I would rate our stay as a 5 star stay. The house is perfect . This property was so much more than I had expected . My favorite part of the house was the window seat in the second floor . This is where I spent most of my time with a book. The house had every amenity to make your stay comfortable. The house is also extremely clean which is very important to me . I will definitely stay here again .
Stayed 5 nights in Aug 2023
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Gaby Y.

Wow
From the minute we walked in to the front door we were impressed. The views from all of the huge windows were spectacular. The house is set up perfectly for a family, with plenty of sleeping space and a wonderful first floor with an open concept, allowing lots of interaction while cooking and eating. The kitchen is very well equipped and made it very easy to have almost all our meals there. We all felt so peaceful and comfortable there. Thank you to the owners for having and sharing such a great spot.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Caden

Great week getaway with friends!
I went to A Shore Thing with a group of college friends over the summer and we had a great time! The House’s location on the Chesapeake was perfect for kayaking since there were very few other boats, and the mornings and evenings brought calm water. The grocery store was conveniently less than a 5 minute drive away, so grabbing things we forgot to buy at the beginning of the week was super easy! We took day outings to Rehoboth beach (a 2 hour drive) and an outlet mall (15 minutes away) which were perfect for young adults entertaining themselves for a week. At night, the media room in the basement was great for watching Netflix shows and movies, and we had no issues making a wide range of full dinners in the kitchen. In addition to cooking, the house was really close to plenty of restaurants including Maryland seafood, pizza, fast food, and an ice cream shop. There’s an Italian deli/ store a few minutes away that’s great for grabbing sandwiches to go for an afternoon out. Also, the Walgreens 5 minutes away was essential for our emergency mid-week aloe vera purchase! Overall we loved the house, the view from the back deck was beautiful, and we will be coming back next summer!
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Diane D.

Awesome Treat
City life is stressful and "A Shore Thing" was a complete getaway from the daily grind. Five minutes in the hammock with the sound of birds chirping and a cool breeze refreshed my soul. The amenities in the home are plentiful and please crowds of all ages. While indoors, the top level of the home has a billiard table and foosball, the main level has abundant board games, and the lower level has a large screen and movie theater seating to provide entertainment. For those that want to lounge, the top level has a beautiful window seat, the main level has a sunroom, and the bottom level has a porch swing which provide views of the water and birds. The water is where I wanted to be though, so multiple jaunts in single and double kayaks were fantastic fun. I look forward to going back again to connect with friends and family while we interact and relax.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Eryn M.

Paradise at The Shore
This immaculate, well-equipped house on the water did not disappoint! The view literally left us speechless. The house is even more beautiful in person. The hardest decision each day was where to sit, relax and reflect on the peacefulness of the water view and watch the birds and boats. This multi-level home has an abundance of outdoor seating and plenty of areas throughout the house for groups to gather and have fun. The house is not far from groceries and restaurants, but you won't want to be gone long! The owner was very responsive and accessible. We will most definitely be coming back; this was the best vacation home we've stayed at.

About the host

Hosted by iTrip Vacations Annapolis - Sean Degnan

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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