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Near Chesapeake Bay: Home w/ Hot Tub, Yard Games!

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Chestertown Vacation Rental | 5BR | 2.5BA | 2,500 Sq Ft
Kitchen | Bar Seating | Coffee Maker | 1st Floor
Wraparound Porch
Home Exterior
Living Room | Fireplace | 1st Floor

Reviews

10 out of 10
Exceptional
5 bedrooms2+ bathroomsSleeps 102500 sq ft

Popular amenities

  • Hot tub on site
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony

Explore the area

View in a map
Chestertown, MD
  • Place, The Mainstay
    ‪12 min drive‬
  • Place, Rock Hall Harbor
    ‪13 min drive‬
  • Place, Waterman’s Museum
    ‪13 min drive‬
  • 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

GENERAL
- Central heating & A/C, ceiling fans
- Washer/dryer, iron/board
- Linens/towels
- Complimentary toiletries, hair dryer
- Free WiFi
- Keyless entry

FAQ
- 1 exterior security camera (facing out)

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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House Rules

Check in after 1:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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

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.
Map
Chestertown, MD

What's nearby

  • The Mainstay - 12 min drive - 14.1 km
  • Rock Hall Harbor - 13 min drive - 14.8 km
  • Waterman’s Museum - 13 min drive - 14.8 km
  • Ferry Park - 14 min drive - 16.2 km
  • Washington College - 17 min drive - 19.8 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 115 min drive

Restaurants

  • ‪Ford's Seafood - ‬11 min drive
  • ‪Tolchester Marina Beach Bar - ‬11 min walk
  • ‪Harbor Shack - ‬14 min drive
  • ‪The Little Lemon Leaf - ‬11 min drive
  • ‪Flyling Decoy Bar & Grill - ‬11 min drive

Frequently asked questions

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 30 Apr, 2026, prices found for a 1-night stay for 2 adults at Near Chesapeake Bay: Home w/ Hot Tub, Yard Games! on 1 Jun, 2026 start from S$1,265, 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.
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Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

8.0/10

Location

6.0/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Cindy D.

Liked: Cleanliness, check-in, communication, location

Beautiful home

Beautiful home and great hospitality. Very clean and smelled amazing (that's important for people who have sensitivity to smells). Comfy beds too.
Stayed 5 nights in Aug 2024
From a partner site

10/10 Excellent

Cara

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!

About the host

Hosted by Evolve

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