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First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown with a fitness center and an outdoor pool

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Property grounds - First Floor Studio Apartment in Historic Chestertown (Chestertown)
Exterior - 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)
Interior - First Floor Studio Apartment in Historic Chestertown (Chestertown)
Property grounds - 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
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

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

Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing
  • Pool
  • Parking included
  • Free WiFi
  • Restaurant
7.8 out of 10, Good, 77 reviews
$113 nightly
The price is $126
Dec 25 - Dec 26
Total with taxes and fees
The Lodge at Great Oak Landing

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
Information provided by the property may be translated using automated translation tools

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
  • Chestertown Historic District - 4 min drive - 2.2 miles
  • Washington College - 5 min drive - 2.6 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 Dec 24, 2025, prices found for a 1-night stay for 2 adults at First Floor Studio Apartment in Historic Chestertown on Dec 25, 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.

How much is parking?

Onsite parking is available at the 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

Exceptional

All reviews shown are from real guest experiences. Only travelers 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.
More informationOpens in a new window
Rating 10 - Excellent. 91 out of 108 reviews
Rating 8 - Good. 13 out of 108 reviews
Rating 6 - Okay. 2 out of 108 reviews
Rating 4 - Poor. 2 out of 108 reviews
Rating 2 - Terrible. 0 out of 108 reviews

9.8

Cleanliness

9.6

Location

9.4

Eco-friendliness

9.8

Property conditions & facilities

Reviews

10/10 Excellent

Christine G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The room was clean, comfortable and quiet. We enjoyed sleeping with the windows open, listening to the night insects in a very peaceful, quiet neighborhood.The bed was comfortable, and the bathroom was spacious with lots of linens, soaps. We especially appreciated the bowl of travel toiletries, first aid needs, cold/sinus needs, and many other travel size products!We didn't get a chance to use the pool, but it looked very inviting. Our host was extremely gracious and promptly responded when we had a question.We highly recommend this apartment, and would stay here again!
Stayed 1 night in Sep 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

Peter E.

Liked: Cleanliness, communication, location, listing accuracy

Chestertown

Lovely. Owners were friendly and helpful. Handy laundry facilities in unit.
Stayed 2 nights in Apr 2025

10/10 Excellent

Jennifer M.

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

Great location and comfortable accommodation

The space was very clean. Communication with the owner was a breeze. It was quiet. The neighborhood is great. It is close to downtown Chestertown. A fabulous stay!
Stayed 2 nights in Mar 2025

8/10 Good

Hilary G.

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

Nice getaway

A comfortable, charming getaway in a great location
Stayed 1 night in Apr 2024

10/10 Excellent

Christine C.

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

Lovely

Clean, well appointed, plenty of space, all small amenities were thought of. We would definitely come back. Very responsive owner too!
Stayed 1 night in Mar 2025

10/10 Excellent

Lesley E.

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

Lovely stay

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 Excellent

Deborah P.

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

Second visit

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 Excellent

Shawn

Liked: Cleanliness, amenities, property conditions & facilities, communication
Very clean, excellent communications,
Stayed 2 nights in Jan 2025

10/10 Excellent

bruce

Liked: Cleanliness, amenities, property conditions & facilities, communication
Access to the pool and hot tub was great! Quiet and easily accessable
Stayed 1 night in Aug 2023

10/10 Excellent

Judi M.

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

Second Visit

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 Excellent

Gary B.

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

Nice place

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 Excellent

Kurt C.

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

Just what we needed

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 I’m glad we did!
Stayed 1 night in Apr 2024

10/10 Excellent

Jean Marie r.

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

short get away to chestertown

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 Excellent

Donald M.

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

Excellent

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

8/10 Good

Bill M.

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

Cozy apartment

Nice apartment in a quiet neighborhood! Lovely surroundings overlooking a golf course.
Stayed 2 nights in Sep 2023

10/10 Excellent

Andrew R.

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

Beautiful Place

This is a very nice room in a beautiful and quiet neighborhood. The hostess was accessible and responsive. Only one minor issue was with the TV and available channels, but we weren't there to watch TV on such a nice time in Chestertown.
Stayed 1 night in Oct 2024

10/10 Excellent

Annie J.

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

Chestertown visit

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 Excellent

Val R.

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

Great location, lovely stay

Very happy I booked this property for my stay in Chestertown. I was attending a wedding close to the property so it was conveniently located, only a few min drive away. Host was very helpful, responsive, and accommodating. The property itself was clean and comfortable. I enjoyed the little touches too like having some drinks stocked in fridge and other things like make up removal wipes, etc. I would stay here again if ever in the area!
Stayed 1 night in May 2024

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

Theresa M.

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

Cozy place to relax

Stayed for a weekend, very nice, cozy place. Very close to town and very quiet, relaxing area. Super clean, comfy bed, good communication from host. Would definitely stay again - it's a great place for a short, relaxing stay when not planning to do any cooking. There's a little fridge and a microwave to heat stuff up, which is all we needed on this trip. Very nice, spacious bathroom with great water pressure in shower, also a washer/dryer available in the unit. They even had nice, fluffy bathrobes for guests!
Stayed 2 nights in Aug 2024

8/10 Good

Craig J.

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

Tv is a pain

Owners are a plus. Location VG. Privacy excelleny
Stayed 2 nights in Aug 2024

6/10 Okay

Diane G.

Liked: Check-in, communication, location

Room for improvement

Check in and out was easy. The room was nice and clean. The deck area was dirty and had 1 broken chair. The pool was not full and the hot tub was not open.
Stayed 2 nights in Aug 2024

8/10 Good

Judy O.

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

Pirate's weekend getaway

Great property, inside accommodations were clean and comfortable. Host was easy to communicate with and very responsive to questions. We wanted to use the hot tub but we didn't know the hot tub was seasonal. The pool had a vacuum in it 24/7 and we were not comfortable swimming in it. I understand that is a mayter of preference. The studio apartment is great for short stays. Would stay there again.
Stayed 2 nights in Aug 2024

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