Entire home

Eastern Shore Hideaway with Grill, Kayaks & Wkend Access Dive Bar & Restaurants

your current months are December, 2024 and January, 2025.
December 2024
January 2025

Photo gallery for Eastern Shore Hideaway with Grill, Kayaks & Wkend Access Dive Bar & Restaurants

Beach nearby, sun-loungers, beach towels
Smart TV, fireplace, video games, ping pong
Terrace/patio
Fridge, microwave, oven, stovetop
Dining

Reviews

10 out of 10

Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 10185.8 sq m

Popular amenities

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

Explore the area

Map
Chestertown, MD
  • The Mainstay
    11 min drive
  • Rock Hall Harbor
    12 min drive
  • Washington College
    17 min drive
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    95 min drive

Room options

Similar properties

About the area

Chestertown

Located in Chestertown, this vacation home is in a rural location, within a 15-minute drive of The Mainstay and Waterman’s Museum. .This family-friendly vacation home is 7.2 mi (11.6 km) from Rock Hall Harbor and 8 mi (12.9 km) from Ferry Park.

What's nearby

  • The Mainstay - 11 min drive
  • Rock Hall Harbor - 12 min drive
  • Washington College - 17 min drive
  • Baltimore Cruise Terminal - 107 min drive
  • Baltimore Inner Harbor Marina - 110 min drive

Getting around

  • Baltimore, MD (MTN-Martin State) - 124 min drive

Restaurants

  • ‪Harbor Shack - ‬14 min drive
  • ‪Waterman's Crab House - ‬12 min drive
  • ‪Java Rock - ‬11 min drive
  • ‪Get The Scoop - ‬11 min drive
  • ‪Fords Seafood - ‬12 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.

Eastern Shore Hideaway with Grill, Kayaks & Wkend Access Dive Bar & Restaurants

Enjoy this oceanfront community at this 2000 sq ft Cape Code Home 5 bedrooms, 2.5 bathrooms which includes an office desk, futon and bunk bed with farm doors for semi-privacy. Has two electric fireplaces, firepit, gaming area with pool table with convertible ping pong table. Walk to Shanty Beach Bar for live music and fun in the sun Friday-Sunday. Enjoy weekend breakfast overlooking the Chesapeake at the Channel Restaurant or enjoy fishing, crabbing or visit a local winery. during the week. Take a dip in the water or settle on the kayaks and float down the ocean stream. Take a bike ride to shops in Rock Hall and pack up the family Saturday morning for a stroll at Chestertown Historic District and pick up fresh produce. During the week, book a fishing charter with the whole family or friends to catch what’s for dinner. Enjoy the Bay Sunday - Saturday at Waterman’s crab house a short drive from the house.

Come relax w/ the whole family or friends at Cape Cod Coastal Experience. On the property, experience included hanging out on the 400 sq ft deck & grill outdoors, escape to the game room, or some of the best BBQ and crab cake in MD.

In the cooler months, relax in front of the firepit or fireplace enjoying hot chocolate and s'mores. Great spot for wedding attendees at the Great Oak Manor or families for students at Washington College or friends who want an ideal get-a-way for quiet time, celebration and good time in a nature habitat. This home has over ten spaces for you to enjoy. Access the deck, grill, games, comfortable seating & BBQ. Take in all nature has to offer watching deer, bald eagles, birds & rabbits.

12 Minutes from Washington College and Great Oak Manor.

Highlighted Features
✅Quiet Area
✅High-speed Internet
✅Private Beach Access
✅2 Kayaks onsite
✅Ramp Access
✅Pool table
✅Ping Pong Table
✅2 Bicycles on-site
✅Deck
✅Outdoor Firepit
✅Grill
✅Cushioned outdoor furniture
✅Card Games
✅Oversize Board Games
✅Four backpack Beach chairs
✅Beach Towels
✅Beach blanket
✅Mini Library
✅Office
✅Coffee Station
✅Fully equipped kitchen
✅Smart TV
✅Basic Cable
✅Washer and Dryer on-site

You are:

2 minute walk to the Shanty Beach Bar (Open weekends from Fri. 3pm until Sunday 6pm)
Beach Marina weekday access limited until 5pm daily
3 minute drive to Boat Ramp/kayaking, swimming etc.
7 minute drive to Rock Hall Beach aka Ferry Park
10 minute drive to Farmers Market
12 minute drive to Washington College
15 minute drive to state-of-the-art multi-generational traditional tennis courts, sand volleyball and basketball courts

Amenities limitations:
*There is a community pool/beach resort-like area 5 minute walk from the house only available on the weekends! Pool passes come with registering your boat for the weekend. If you don't have a boat, you won't be able to access this pool. The pool is open from May (after Memorial Day) to Sept. No pool access 24 Sept -May 15 timeframe.
*There is a community pool within 15 minutes driving distance. You can access for $7 a day per person.
*If you have a boat, you can access the boat ramp and drop your boat.
*The two restaurants to include the beach bar are open on the weekends starting Friday at 3pm and closes Sunday at 6pm EST. Friday and Saturday it is scheduled to close at 11pm but may go later.
* There is live music at the Shanty so expect to hear noise/music on Friday and Saturday nights.
In town, restaurants and some of the shopping stores close as early as 7pm during the week so govern yourself accordingly. Phat Daddy's is also closed on Mondays.
* Highly recommend your first trip to the property is before night fall as the roads are dark at night and can be intimidating/scary if you are traveling along or not comfortable traveling in more remote locations.
*For some carriers reception can be spotted, so have print out directions or at a minimum take a screenshot of the last 10 miles/minutes of the directions.
*Closest gas station is about 10 minutes/8 miles away so govern yourself accordingly.community
Make yourself comfortable in this air-conditioned vacation home, which features a fireplace and a Smart TV. There's a private patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Enjoy recreation amenities such as a fitness center or take in the view from a garden. This vacation home also features an arcade/game room and barbecue grills.
Guests will find features like internet access and onsite parking.

Property manager

Jill Bulluck

Languages

English

Property amenities

Beach

  • Near the beach
  • Beach sunloungers
  • Beach towels

Internet

  • Free WiFi

Parking and transport

  • On-site parking

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Blender
  • Coffee grinder
  • Toaster
  • Ice maker

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bed sheets provided
  • Sofa bed

Bathrooms

  • 2.5 bathrooms
  • Bath or shower
  • Toilet paper
  • Soap
  • Hairdryer
  • Towels provided
  • Shampoo

Living spaces

  • Fireplace
  • Living room
  • Dining room

Entertainment

  • Smart TV with cable/satellite service
  • Pool or billiards table
  • Ping pong table
  • Games room
  • Video games
  • Books
  • Games

Outdoor areas

  • Patio
  • Barbecue
  • Garden
  • Outdoor furniture
  • Firepit

Laundry

  • Washing machine and dryer
  • Near a laundromat

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 1 total (up to 23 kg per pet)
  • Welcoming dogs only

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Safe
  • Iron/ironing board
  • Local meal delivery service

Location highlights

  • In a rural location
  • Near a hospital

Things to do

  • Fitness centre
  • Water sports equipment
  • Kayaking on site
  • Cycling on site
  • Cycling nearby
  • Fishing nearby
  • Basketball nearby
  • Marina nearby
  • Power boating nearby
  • Kayaking nearby

Safety features

  • Carbon monoxide detector installed (host has indicated that there is a carbon monoxide detector on the property)
  • Smoke detector installed (host has indicated that there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • Unit size: 2000 sq ft (185.8 sq m)

Policies

Check-in

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

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
1 total (up to 50 lbs per pet)
Note from host: Pets are not allowed on the furniture.

Children and extra beds

Children are welcome

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
Parties and events (including family gatherings and weddings) are allowed on site; maximum attendees: 15
Note from host: Must be pre-approved
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
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

Eastern Shore Hideaway with Grill, Kayaks & Wkend Access Dive Bar & Restaurants Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 11 out of 12 reviews" "
Rating 8 - Good. 1 out of 12 reviews" "
Rating 6 - Okay. 0 out of 12 reviews" "
Rating 4 - Poor. 0 out of 12 reviews" "
Rating 2 - Terrible. 0 out of 12 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Merrilyn W.

Liked: Cleanliness
Tolchester House
The Tolchester house is a lovely house with five nice bedrooms, a large back deck, a very easy to work in kitchen and a garage full of games. It is with in walking distance of the beach, marina and Shanty bar which really provides as much entertainment as you can ask for. We did go to “Pirates and Wenches” weekend in nearby Rock Hall which was great fun. We used the house as an overflow option for my family and it worked very well.
Stayed 3 nights in Aug 2024

8/10 Good

Jessica N.

Liked: Cleanliness
Couples Getaway
A nice place to stay if your looking to getaway from the city and enjoy the Marinina life in a very quiet neighborhood with beautiful wildlife to see
Stayed 3 nights in Jun 2024

10/10 Excellent

Craig G.

Liked: Cleanliness
Great location for a boating vacation
We normally boat on the upper Chesapeake Bay and wanted to boat on different area of the bay. We rented a transient slip at the Tolchester Marina while staying at this bay house. We found the accommodations at this house to be wonderful. The house was clean and well equipped and plenty of space for my family of 7. Probably the most important thing to say - there was an unforeseen issue with the house water system. Jill was extremely concerned and very promptly had technicians coming to the rescue. All was fixed and we continued on with our vacation. Without a doubt, we would stay at this property again.
Stayed 7 nights in Jul 2023

10/10 Excellent

Alice N.

Liked: Cleanliness
Wonder stay
Great place to stay.
Stayed 6 nights in Jan 2023

10/10 Excellent

Ruth H.

Liked: Cleanliness
Retirement weekend
Place was perfect for our group. Wonderful kitchen with fireplace. Weather didn't allow for any outdoor activities unfortunately. Highly recommend.
Stayed 3 nights in Jun 2023

10/10 Excellent

Paula L., Washington DC

Liked: Cleanliness
Wonderful Home!
We stayed at this charming home for a weekend while two of us competed on the Rock Hall triathlon - and it was just perfect! Immaculate, comfortable, just as pictured. And the host Jill has created a very welcoming and experience, and was incredibly responsive, checking in over the weekend and answering questions promptly. Highly recommend!
Stayed 2 nights in Jun 2023

10/10 Excellent

Danielle B.

Liked: Cleanliness
Wonderful vacation home!!
We had a wonderful time staying here for a girls trip. The house was very nice, spacious, and clean. It had everything you could possibly ever need, and more which was so nice! The host was absolutely amazing from the very beginning of booking through our entire stay. She provided us with a lot of helpful information, left us a lot of extra useful items, and checked in during our stay to make sure everything was going well. The location was great! We lucked out with great weather and were in walking distance to the beach and tiki bar where we spent most of our time. During the mornings and nights we enjoyed relaxing on the back deck where it was quiet and secluded. We had no issues with cell phone service although the host was nice enough to warn us that it could be choppy in some areas. We are already talking about coming back here again next year! Highly recommend to any type of group (the house even had plenty of baby items)!
Stayed 2 nights in Jun 2023

10/10 Excellent

Liz F.

Liked: Cleanliness
Perfect getaway
Super cute house with 4 spacious bedrooms and an office upstairs. House is beautifully decorated with comfortable beds and linens. Jill has truly thought of everything. There are some snacks and basic pantry items as well as condiments and drinks in the fridge (always helpful after a long journey!) There is wood left for use in the fire pit put back, which we absolutely loved having access to. The weather didn’t cooperate for us so we didn’t get to take advantage of the kayaks but knowing they are there for guests use if a wonderful amenity. This home is dog-friendly, but it’s so clean you wouldn’t know it! Again Jill has thought of everything, there is a dog bed, treats, even special towels in the garage! If you are thinking of visiting the Chestertown/ Rock Hall area, you can’t go wrong booking your stay here. We’ll definitely be back.
Stayed 2 nights in Apr 2023

10/10 Excellent

PJ H.

Liked: Cleanliness
Very nice!
Needed a place to stay for an important weekend while visiting local family in the area. Very clean! Jill was super responsive, even when we arrived late.
Stayed 2 nights in Feb 2023

10/10 Excellent

Alice N.

Liked: Cleanliness
Wonder property
Beautiful property with all the amenities and the location is perfect!
Stayed 3 nights in Jan 2023

10/10 Excellent

Joseph C., Elkridge

Liked: Cleanliness
Tolchester Beach Anniversary Getaway
Choose this location to celebrate our anniversary. This place was great and very quiet location. Our host was great and just a short drive to downtown Chestertown with some great restaurants. Would definitely choose it again in the future
Stayed 3 nights in Oct 2022

10/10 Excellent

Theresa C.

Liked: Cleanliness
Beautiful and clean house!
The house was very inviting, extremely clean and very well stocked with everything you need. We thoroughly enjoyed our stay! Thank you Jill for checking in with us and making us feel at home!
Stayed 4 nights in Aug 2022