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Entire apartment

First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown with a fitness center and an outdoor pool

Photo gallery for First Floor Studio Apartment in Historic Chestertown

Property grounds - First Floor Studio Apartment in Historic Chestertown (Chestertown)
Interior - First Floor Studio Apartment in Historic Chestertown (Chestertown)
1 bedroom, in-room safe, free WiFi, bed sheets - First Floor Studio Apartment in Historic Chestertown (Chestertown)
Property grounds - First Floor Studio Apartment in Historic Chestertown (Chestertown)
Exterior - First Floor Studio Apartment in Historic Chestertown (Chestertown)
Escape to a serene private residence, where lush grounds and an inground pool await. Relax in the seasonal hot tub or unwind on the outdoor seating area, surrounded by nature's beauty. With a fully-equipped studio apartment featuring a queen-sized bed, washer/dryer, and lux robes at your disposal.

Reviews

9.6 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 3

Popular amenities

  • Hot Tub
  • Dryer
  • Gym
  • Parking available
  • Washer

Add dates for prices

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 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

Similar properties

Property grounds

Historic Downtown Garden Oasis with Private Patio

  • Kitchen
  • Free WiFi
  • Air conditioning
  • Outdoor Space
10.0 out of 10, Exceptional, 43 reviews
Historic Downtown Garden Oasis with Private Patio

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

Rules

There is a 0 smoking tolerance policy. Any evidence of inside smoking will result in a $250 fee.
Pets may not be left alone. No pets in the pool.
Any evidence of illicit drug use will result in a $500 fee, immediate eviction without refund and notification of law enforcement.

Access methods

Private entrance

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
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 neighborhood

Map
Chestertown, MD

What's nearby

  • Wilmer Park - 3 min drive - 1.8 miles
  • River Arts Chestertown - 4 min drive - 2.2 miles
  • Historical Society of Kent County Maryland - 4 min drive - 2.2 miles
  • Washington College - 5 min drive - 2.6 miles
  • Rolphs Wharf Marina - 14 min drive - 7.8 miles

Getting around

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

Restaurants

  • ‪Milano's Pizzeria - ‬8 min drive
  • ‪Royal Farms - ‬4 min drive
  • ‪Royal Farms - ‬7 min drive
  • ‪Dunkin - ‬6 min drive
  • ‪Procolino's - ‬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 Nov 8, 2025, prices found for a 1-night stay for 2 adults at First Floor Studio Apartment in Historic Chestertown on Nov 10, 2025 start from $99.0, 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. 89 out of 105 reviews
Rating 8 - Good. 12 out of 105 reviews
Rating 6 - Okay. 2 out of 105 reviews
Rating 4 - Poor. 2 out of 105 reviews
Rating 2 - Terrible. 0 out of 105 reviews

9.8/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

9.4/10

Eco-friendliness

Reviews

10/10 Excellent

Randy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chestertown Retreat

Wonderful stay in a beautiful location convenient to everything. Host was outstanding.
Stayed 1 night in Jun 2025

10/10 Excellent

Victoria P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely area with shaded parking, spacious room, very clean. Plenty of towels and amenities. We had to cut the trip short due to an emergency, but thoroughly enjoyed our short stay. There was a bit of water in the refrigerator and the owners were very responsive.
Stayed 5 nights in Jul 2025

10/10 Excellent

Mark D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Very quiet, home-like, personable

Excellent accommodations
Stayed 2 nights in May 2024

10/10 Excellent

Maika Y.

Disliked: Cleanliness, check-in, communication, location, listing accuracy

Great stay

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

10/10 Excellent

marcy s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous property :)

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 Excellent

Dustin P.

Disliked: Cleanliness, check-in, communication, location, listing accuracy

Vacation

All good as described
Stayed 5 nights in Jul 2023

10/10 Excellent

Liane D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding weekend

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

10/10 Excellent

Erin E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

PERFECT!

This spot is a GEM in Chestertown-so close to everything downtown, within walking distance. Check in was a breeze. The space was spotless, like eat off the floors clean. Comfy bed, stocked fridge for us, it was perfect for a night away. Would HIGHLY recommend staying here if you're in the area!
Stayed 1 night in Feb 2023

10/10 Excellent

Rhonda P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Just right & very convenient!

Thanks so much for accommodating our pre-wedding stay! My son & his groomsman enjoyed their brief but comfortable and quiet stay at your place and I can’t thank you enough for your hospitality! It made all the difference!
Stayed 2 nights in Apr 2024

10/10 Excellent

Kristen M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent and convenient property.

This apartment was excellent in every way. Only 2 miles from downtown Chestertown in a beautiful, quiet neighborhood. Property and apartment were immaculate. Loved having access to the pool and hot tub. Communication with property owners was maybe the best I have ever had with any VRBO say. Will definitely book again.
Stayed 1 night in Jun 2023

8/10 Good

Jeff B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nicely furnished room

Very nicely furnished and clean room. The only reason I gave it 4 instead of 5 stars was that the television had a fire stick and was hard to navigate and the bed had a foam mattress that was not comfortable.
Stayed 2 nights in Apr 2023

10/10 Excellent

linda s.

Liked: Cleanliness, check-in, communication, location, listing accuracy

nice room in a nice neighborhood

Clean bedroom with bathroom and washer/dryer to stay in while visiting family in the area. The neighborhood is quiet. Our privacy was respected. Owners were available to address our questions. We hope to meet them when we visit again. Linda and Dave
Stayed 2 nights in Mar 2022

10/10 Excellent

Karen M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We Would Love to Return

Our living area was just as stated on VRBO. Our hosts were lovely and always available if we had a need. Our room was very clean, with absolutely beautiful and quiet surroundings - just what we needed. The short drive to such a friendly community added to our experience..We did enjoy sitting on our private little deck. Thank you, Cunninghams! So enjoyed and we added a wonderful memory!
Stayed 4 nights in May 2023

10/10 Excellent

Elizabeth L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect for our needs

Stayed here to move my daughter into her dorms so we just used it for an overnight and it was perfect for us. The fold out futon was a little small for my daughter so she just slept in bed with me. When I bring my five year-old with me to visit, that could work for him. So for us it was perfect fit. The room was clean and ready, and the host was amazing at communication. Thank you for our stay!
Stayed 1 night in Aug 2024

10/10 Excellent

Darlene F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Studio

We were only here for one night but this studio had everything we needed and more. The owner was very hospitable and accommodating. My granddaughter swam in the inviting pool with the owner’s two children and had a blast. It was very private although attached to the main home. The mini fridge was stocked up with a few drinks and the microwave came in handy. If we are in the area again, this would be a great choice!
Stayed 1 night in Jul 2022

10/10 Excellent

Barbara

Liked: Cleanliness, amenities, property conditions & facilities, communication
We liked the hot tub tho' it wasn't very hot. Comfortable bed. Spacious bathroom. Some items were missing. For example there was a nice coffee maker but no mug or cup. The table and chairs were inadequate: not comforatable or useful to write or eat. The host was responsive.
Stayed 2 nights in Aug 2023

4/10 Poor

Kim H., -

Liked: Cleanliness, check-in, location
Disliked: Listing accuracy

Could have been better

There was no coffee available, the cot bed was extremely uncomfortable for my daughter and there was no TV satellite/cable available which was listed under amenities. They also list dishes and utensils but none of that was there. Also the dining table they have is a tiny outdoor cafe set with foldable chairs. Very uncomfortable. No where other than the bed to sit comfortably.
Stayed 2 nights in Oct 2023

10/10 Excellent

Mary

Liked: Cleanliness, amenities, property conditions & facilities, communication
A charming studio in a quiet neighborhood. great directions from host on how to use the property -
Stayed 1 night in Aug 2025

10/10 Excellent

Susan A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place was appealing with a private entrance. The swimming pool was a big plus for our granddaughters who play in it most every day as the air temperature was very hot . Alerted the owner to a malfunctioned door and she replied immediately. All in all an enjoyable stay!
Stayed 7 nights in Jul 2025

10/10 Excellent

Balon T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Easy

Booking, the stay, and the communication was great. Cute downtown within a mile and half. Room was spacious, clean, and had everything you need.
Stayed 4 nights in Jul 2025

10/10 Excellent

Mindy

Liked: Cleanliness, amenities, property conditions & facilities, communication
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 90° 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, etc… 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 Excellent

Mario

Liked: Cleanliness, amenities, property conditions & facilities
Very pretty location. Few minutes drive to town center.
Stayed 1 night in Jun 2025

10/10 Excellent

Jackie O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great situation for us in every way.
Stayed 3 nights in May 2025

10/10 Excellent

Betsy T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect

An exceptionally clean studio with plenty of space, a large full bath and comfortable bed. The owner also provided lots of nice extras.
Stayed 1 night in May 2025

10/10 Excellent

Valarie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent for short stay

Perfect set up for a short stay. Refrigerator, microwave and nespresso machine provided so basics are covered. Would definitely stay here again.
Stayed 2 nights in May 2025