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First Floor Studio Apartment in Historic Chestertown

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Relax by the pool surrounded by a tranquil golf course view.
Guests can enjoy a balcony with a staircase leading to a peaceful outdoor space.
Efficient laundry facilities with a front-loading washer and dryer.
Relax in this inviting bedroom with a large bed, ceiling fan, and a beautiful painting of sailboats.
Enjoy the serene garden surrounded by a variety of flowering plants and a tall tree.

Reviews

9.6 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 3

Popular amenities

  • Hot tub
  • Dryer
  • Washer
  • Parking available
  • Gym

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

First Floor Studio Apartment in Historic Chestertown

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped with a queen sized bed, linens, washer/dryer, microwave, refrigerator, dinette, toiletries, lux robes... everything you could possibly need to escape the hustle and bustle of life. An additional sleeper sofa, crib, etc. are available at request. Walk to the waterfront or historic district, ride bikes on back country roads. We are more than happy to help arrange paddleboard and kayak adventures! *We require guests to have a verified profile by VRBO OR verification by ID prior to stay*

Property manager

Elisabeth Cunningham

Languages

English

Add dates for prices

Property amenities

Beach

  • Beach towels

Pool/Spa

  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Street parking available
  • Parking on site

Food and drink

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Ice maker
  • Microwave
  • Paper towels
  • Refrigerator

Dining

  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Safe

Location highlights

  • In a rural location
  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping mall
  • Near the bay
  • Near the marina
  • Next to a golf course

Things to do

  • Golf
  • Gym
  • Optional golf privileges
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours 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)
  • First aid kit
  • Fire extinguisher

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10.0 out of 10, Exceptional, 35 reviews
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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 20

Check-out

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

Special check-in instructions

Guests can access their accommodation through a private entrance
You will receive an email from the host with check-in and check-out instructions

Access methods

Private entrance

Pets

Pets not allowed

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
Onsite parties or group events are strictly prohibited
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 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
Property Registration Number 025962

About the area

Map
Chestertown, MD

What's nearby

  • Wilmer Park - 4 min drive - 2.8 km
  • River Arts Chestertown - 5 min drive - 3.5 km
  • Historical Society of Kent County Maryland - 5 min drive - 3.5 km
  • Washington College - 6 min drive - 4.2 km
  • Rolphs Wharf Marina - 17 min drive - 12.5 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 110 min drive

Restaurants

  • ā€ŖMcDonald's - ā€¬7 min drive
  • ā€ŖDining Hall - ā€¬6 min drive
  • ā€ŖProcolino Pizza - ā€¬6 min drive
  • ā€ŖChina House - ā€¬6 min drive
  • ā€ŖThe Freeze - ā€¬6 min drive

Frequently asked questions

Does First Floor Studio Apartment in Historic Chestertown have a pool?

Yes, this property has an outdoor pool.

How much does it cost to stay at First Floor Studio Apartment in Historic Chestertown?

As of Jul 14, 2025, prices found for a 1-night stay for 2 adults at First Floor Studio Apartment in Historic Chestertown on Jul 17, 2025 start from CA $135.55, excluding 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 First Floor Studio Apartment in Historic Chestertown pet-friendly?

No, pets are not allowed at this property.

What time is check-in at First Floor Studio Apartment in Historic Chestertown?

Check-in begins at 4:00 PM.

What time is check-out at First Floor Studio Apartment in Historic Chestertown?

Check-out is at 11:00 AM.

Where is First Floor Studio Apartment in Historic Chestertown located?

Situated in Chestertown, this golf apartment building is within 3 mi (5 km) of Wilmer Park, Sumner Hall, and Chestertown Historic District. River Arts Chestertown and Garfield Center for the Arts at the Prince Theater are also within 3 mi (5 km).

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First Floor Studio Apartment in Historic Chestertown Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 75 out of 90 reviews
Rating 8 - Good. 11 out of 90 reviews
Rating 6 - Okay. 2 out of 90 reviews
Rating 4 - Poor. 2 out of 90 reviews
Rating 2 - Terrible. 0 out of 90 reviews

9.6/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

9.2/10

Eco-friendliness

Reviews

10/10

Very pretty location. Few minutes drive to town center.
Stayed 1 night in Jun 2025

10/10

Quiet neighborhood and the best place to stay.
Stayed 1 night in Aug 2024

10/10

This property was perfect! Host was very communicative and quick to respond to even the simplest of questions. Entry was a breeze, and air-conditioning unit worked to keep it cool even in 90Ā° weather. I had everything I needed to be comfortable. Plenty of space to work out, sit and eat my meals, get some work done, and also do laundry before leaving. They have supplied so many basic needs as well. Coffee, toiletries, bottled water, etcā€¦ I walked the neighborhood for a few miles, and did not run into any vehicles on roads or people while walking. It was so peaceful and quiet! I would definitely stay again!
Stayed 3 nights in Jun 2025

10/10

We had a wonderful stay. The apartment was lovely, clean and very close to town. Highly recommend!
Stayed 1 night in Oct 2024

10/10

The room and bathroom were very spacious and clean! I love and appreciate the small toiletries that were left for us! The small refrigerator and table are a nice touch that we used during our stay!
Stayed 1 night in Nov 2024

10/10

Our second time staying at this property did not disappoint. Beautiful home, great location. Hosts are wonderful and easy to communicate with.
Stayed 1 night in Dec 2024

10/10

Very clean, excellent communications,
Stayed 2 nights in Jan 2025

10/10

Excellent accommodations
Stayed 2 nights in May 2024

10/10

This was super comfortable, and the hosts were exceptionally generous! I highly recommend!
Stayed 2 nights in Mar 2023

10/10

Very easy to get into, very clean, the owners, make it very easy and will definitely stay again
Stayed 1 night in Jan 2023

10/10

This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year.
Stayed 2 nights in Feb 2025

10/10

This was our second stay and we will most definitely be repeat visitors. Spacious room, easy check in and communication with owner, lovely property and area!
Stayed 1 night in Feb 2024

10/10

The property was clean and comfortable and the owners were friendly and were quick to reply. I would definitely stay again.
Stayed 1 night in Jul 2022

10/10

We had a wonderful stay at this Chestertown property and enjoyed it's close proximity to town, cleanliness, and comfort!
Stayed 1 night in Apr 2023

10/10

EasyvPeasy place.
Stayed 1 night in Nov 2024

10/10

Enjoyed a getaway to Chestertown. Apartment was very nice.
Stayed 2 nights in Feb 2023

8/10

Loved the backyard view onto the golf course.
Stayed 2 nights in Sep 2022

10/10

This was our second stay at this Vrbo in Chestertown. It was just as perfect for our second stay. It is very clean, quiet and comfortable and in a beautiful location.
Stayed 3 nights in May 2023

10/10

It was a nice room in a nice neighborhood. Only complaint would be the coffee maker was awful.
Stayed 2 nights in May 2024

10/10

This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and Iā€™m glad we did!
Stayed 1 night in Apr 2024

10/10

This studio apt is wonderful. It is well appointed with robes and nice soaps. The host Elizabeth is very communicative and quickly responds and is so helpful and kind.
Stayed 3 nights in Jul 2024

10/10

very nice
Stayed 1 night in Oct 2023

10/10

Just what we needed for the night! Thank you
Stayed 1 night in Aug 2024

10/10

My husband and I are relocating to Chestertown, and this was a great introduction. The space was very clean, nice location, well decorated, and comfortable! We would stary here again!
Stayed 4 nights in Dec 2023

10/10

Comfortable and clean room stocked with everything you need. Was perfect for an overnight in Chestertown! The owner was also very easy to work with.
Stayed 1 night in Feb 2023