Escape to a serene waterfront retreat in Chestertown, where this spacious home offers 5 bedrooms and a wraparound porch. Enjoy the hot tub/cold plunge, fishing and crabbing nearby or take scenic drives to quaint shops and restaurants in town. With bicycles, board games, outdoor seating areas, high-speed WiFi plus TVs with bar seating for cozy movie nights.
Reviews
1010 out of 10
Exceptional
Entire home
5 bedrooms3 bathroomsSleeps 10232 sq m
Popular amenities
Spa pool
Kitchen
Washing machine
Dryer
Air-conditioning
Outdoor space
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.
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
Property amenities
Pool/Spa
Hot tub
Internet
Available in the house: Internet access
Parking and transport
Onsite parking options include a garage
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Microwave
Refrigerator
Toaster
Bedrooms
5 bedrooms
Bedsheets provided
Bathroom
2.5 bathrooms
Hair dryer
Towels provided
Living spaces
Fireplace
Entertainment
Games
TV with cable/satellite channels
Outdoor areas
Balcony
Laundry
Laundry facilities
Washing machine
Work spaces
Desk
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Smoke-free property
Services and conveniences
Iron/ironing board
Location highlights
Near the marina
Things to do
Bicycles
Hunting nearby
Motor boating nearby
Safety features
Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets not allowed
Children and extra beds
Children are welcome
Events
No events 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 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
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
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. Visit our Chestertown travel guide
Is Near Chesapeake Bay: Home w/ Hot Tub, Yard Games! pet-friendly?
No, pets are not allowed at this property.
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).
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Near Chesapeake Bay: Home w/ Hot Tub, Yard Games! Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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!