Entire home

Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Photo gallery for Cozy 1-bedroom in-law suite in lovely Chestertown with AC

A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.
A deck with outdoor furniture, a potted plant, and a house in the background.
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.
A house with a blue door, a front porch, and a garden with various plants and flowers.
A shower with a handheld showerhead and a wall-mounted faucet.

Reviews

8.0 out of 10
Very good

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
1 bedroom1 bathroomSleeps 4

Popular amenities

  • Patio
  • Outdoor pool
  • Air conditioning
  • Refrigerator
  • Internet
  • Onsite parking available

Explore the area

View in a map
Chestertown, MD
  • Place, Chestertown Historic District
    ‪6 min drive‬
  • Place, River Arts Chestertown
    ‪6 min drive‬
  • Place, Washington College
    ‪6 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪130 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Living Room 1

1 Queen Bed

Primary bedroom

1 Queen Bed

1 bathroom

Bathroom 1

Towels provided · Bathtub or shower · Toilet

Spaces

Deck or patio
Number of living rooms
Garden

About this property

Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Private 1-Bedroom Retreat in Chestertown, MD

Skip the traditional hotel and enjoy your own private 1-bedroom, full-bath retreat with 1,200+ sq. ft. of comfortable living space!

Perfect for a weekend getaway, visiting family, a Washington College visit, or simply enjoying a relaxing stay on Maryland’s Eastern Shore.

Your stay includes:
• Private entrance
• Spacious bedroom & full bath
• Large open living room
• Kitchenette
• Washer & dryer in the unit
• Seasonal Pool access
• Large backyard space
• Grill & firepit
• Air mattress available for additional sleeping space

Great Chestertown Location!

Enjoy being close to Washington College and historic downtown Chestertown, a charming waterfront town along the Chester River. Downtown offers locally owned boutiques, galleries, cafés, restaurants and plenty of small-town Eastern Shore character. (Washington College⁠)

On Saturday mornings, visit the popular Chestertown Farmers Market at Fountain Park, a local tradition featuring fresh produce, baked goods, flowers, artisan products and handmade goods. The market is held Saturdays from 8 AM–noon year-round, weather permitting during the winter season. (Chestertown MD⁠)

Spend the day exploring Chestertown, then come back, grill dinner and relax around the firepit.

More space. More privacy. More ways to relax than your average hotel room. Please keep in mind host is onsite. If you would like to use the grill, and/or firepit, please let the host know so as to avoid any overlaps and proper preparation. There are three dogs kept in the main house that will be kept in a separate area out of sight and away from guest areas.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

Events allowed: family gatherings, birthday parties, weddings
Special events require advance notice
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you complete the following before checking out:
Remove personal items and remove leftover food and drinks
Turn off the lights, lock the doors, and return the keys
Please leave the property in the condition you found it.
Please set the thermostat to 80.
Please be sure all lights are turned off and doors are locked.
Failure to complete these may result in a negative review from the host.

Important information

You need to know

Property # 5443939
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, birthday parties and weddings) are allowed on site; maximum attendees: 30
Note from host: Special events require advance notice
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
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Chestertown

Located in Chestertown, this vacation home is near the beach. Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are cultural highlights, and some of the area's activities can be experienced at Rolphs Wharf Marina and Cassinelli Winery and Vineyards. Schooner Sultana and Larrabee Arts Center are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hunting and mountain biking nearby.
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Map
Chestertown, MD

What's nearby

  • Chestertown Historic District - 6 min drive - 7.0 km
  • Historical Society of Kent County Maryland - 6 min drive - 7.0 km
  • River Arts Chestertown - 6 min drive - 7.3 km
  • Washington College - 6 min drive - 7.6 km
  • Rolphs Wharf Marina - 6 min drive - 4.2 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 113 min drive

Restaurants

  • ‪McDonald's - ‬9 min drive
  • ‪Royal Farms - ‬4 min drive
  • ‪Dunkin - ‬9 min drive
  • ‪Procolino's - ‬9 min drive
  • ‪Royal Farms - ‬7 min drive

Frequently asked questions

Does Cozy 1-bedroom in-law suite in lovely Chestertown with AC have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at Cozy 1-bedroom in-law suite in lovely Chestertown with AC?

As of Sep 23, 2026, prices found for a 1-night stay for 2 adults at Cozy 1-bedroom in-law suite in lovely Chestertown with AC on Oct 5, 2026 start from $293, 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.

Is Cozy 1-bedroom in-law suite in lovely Chestertown with AC pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Cozy 1-bedroom in-law suite in lovely Chestertown with AC?

Check-in begins at 3:00 PM.

What time is check-out at Cozy 1-bedroom in-law suite in lovely Chestertown with AC?

Check-out is at 11:00 AM.

Where is Cozy 1-bedroom in-law suite in lovely Chestertown with AC located?

Situated near the beach, this vacation home is 2.4 mi (3.8 km) from Rolphs Wharf Marina and 2.9 mi (4.7 km) from Kings Town Park. Historical Society of Kent County Maryland and Chestertown Historic District are also within 6 mi (10 km).

Reviews

8.0

Very Good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 0 out of 1 reviews
Rating 8 - Good. 1 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

8.0/10

Cleanliness

6.0/10

Check-in

8.0/10

Communication

10/10

Location

8.0/10

Listing accuracy

Reviews

Verified review

8/10 Good

Liked: Cleanliness, communication, location, listing accuracy
Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living room. Otherwise, I loved the place and its location.
Stayed 3 nights in Sep 2026

About the host

Hosted by Joelle Dolch

Host profile image
We are native to Chestertown for 11 years. I enjoy providing a relaxing space for guests to enjoy this area that has grown so close to my heart.

Why they chose this property

The neighborhood is very walkable and peaceful. Located on a quite cul-de-sac provides a relaxing environment.

What makes this property unique

Our property offers a unique blend of privacy even though it is attached to the main house. We are withing a few short miles to historic Chestertown and Washington College making us an ideal location. We offer a very enjoyable back yard space with additional amenities such as a basketball court, yard to play in, soccer goal, and tot play equipment. The back yard space is very versatile, enjoyable and relaxing, providing something for everyone.

Languages:

English
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