Enjoy the convenience of garage parking - a rare offering in the area.
Centrally-located
You're never far from where you need to be with this convenient location.
5 bedrooms2+ bathroomsSleeps 10
Popular amenities
Balcony
Spa pool on site
Air-conditioning
Garage parking available
Refrigerator
Internet
Explore the area
Chestertown, MD
The Mainstay
Place, The Mainstay
12 min drive
Rock Hall Harbor
Place, Rock Hall Harbor
13 min drive
Waterman’s Museum
Place, Waterman’s Museum
13 min drive
Baltimore, MD (MTN-Martin State)
Airport, Baltimore, MD (MTN-Martin State)
142 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 Queen Bed
Bedroom 5
2 Single Beds and 2 Double Beds
2 bathrooms, 1 half bathroom
Full Bathroom
Full Bathroom
Half Bathroom
Spaces
Deck or patio
Kitchen
Balcony
About this property
Near Chesapeake Bay: Home w/ Hot Tub, Yard Games!
'Chesapeake Bay Beauty' | Ideal for Family Reunions
Your Eastern Shore escape awaits at this stunning 5-bedroom, 2.5-bath modern farmhouse. Just steps from Tolchester Marina and minutes from Rock Hall and downtown Chestertown, this light-filled home blends classic charm with a cozy fireplace and open layout. Relax on the wraparound porch, soak in the hot tub, or enjoy a game on the bocce court. Perfect for family reunions or peaceful retreats, it’s the ideal spot to make lasting memories!
-- THE PROPERTY --
SLEEPING ARRANGEMENTS - Bedroom 1: 1 king bed - Bedroom 2: 1 king bed - Bedroom 3: 1 king bed - Bedroom 4: 1 queen bed - Bedroom 5: 2 bunk beds (twin/full) - Additional Sleeping: 1 portable crib
KITCHEN - Stove/oven, refrigerator, microwave, dishwasher - Drip coffee maker, toaster, spices - Cooking basics, dishware & flatware - Island w/ bar seating, high chair
INDOOR LIVING - Ample entertainment space (ideal for reunions & coastal retreats) - Smart TVs - Electric fireplace - Hardwood floors, open layout - Board games, books
OUTDOOR LIVING - Hot tub/cold plunge - Porch swing, private bocce ball court, bicycles - Expansive wraparound porch - Spacious yard surrounded by trees for privacy and tranquility - Plenty of seating for lounging & dining
ACCESSIBILITY - 2-story home, 4 exterior steps to enter - 1 bedroom & full bathroom on 1st floor
PARKING - Driveway (10 vehicles)
-- THE LOCATION --
- 1 block to Tolchester Beach & Marina - 5 miles to Rock Hall - 10 miles to historic downtown Chestertown’s shops, restaurants, & waterfront - Easy access to boating, fishing, cycling, & Eastern Shore charm - 80 miles to Baltimore/Washington Int'l Thurgood Marshall Airport
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in
ADDITIONAL INFORMATION - This 2-story home requires 4 exterior steps to enter; the 1st floor includes a bedroom and a full bathroom - Your safety matters. This property features a Ring doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device
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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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
About the area
Chestertown
Chestertown is home to this holiday home. The Mainstay and Waterman’s Museum are cultural highlights, and some of the area's attractions include Larrabee Arts Center and Garfield Center for the Arts at the Prince Theater. Power boating offers a great chance to get out on the surrounding water, or you can seek out an adventure with hunting nearby.
Is Near Chesapeake Bay: Home w/ Hot Tub, Yard Games! pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Near Chesapeake Bay: Home w/ Hot Tub, Yard Games!?
As of 15 June 2026, prices found for a 1-night stay for 2 adults at Near Chesapeake Bay: Home w/ Hot Tub, Yard Games! on 22 June 2026 start from AU$1,363, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Near Chesapeake Bay: Home w/ Hot Tub, Yard Games!?
On-site parking is available at the property.
What time is check-in at Near Chesapeake Bay: Home w/ Hot Tub, Yard Games!?
Check-in begins at 1:00 PM.
What time is check-out at Near Chesapeake Bay: Home w/ Hot Tub, Yard Games!?
Checkout is at 11:00 AM.
Where is Near Chesapeake Bay: Home w/ Hot Tub, Yard Games! located?
This family-friendly Chestertown holiday home is within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay. The Mainstay and Ferry 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.
Beautiful home and great hospitality. Very clean and smelled amazing (that's important for people who have sensitivity to smells). Comfy beds too.
Cindy D.
Stayed 5 nights in Aug 2024
From a partner site
10/10 Excellent
Cara
20 Aug 2024
Beautiful
We had a wonderful time in this beautiful home! The home itself was just a super short drive or nice walk to the Tolchester Marina where we spent a good bit of time but the home itself was amazing and had everything we needed and Maureen was a wonderful host! Can’t wait to go back!