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Apartment

First Floor Studio Apartment in Historic Chestertown

Photo gallery for First Floor Studio Apartment in Historic Chestertown

Back Yard
Property grounds
Bed
Property grounds
Pool

Reviews

9.6 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
1 bedroom1 bathroomSleeps 3

Popular amenities

  • Private pool
  • Onsite parking available
  • Washer/dryer
  • Air-conditioning
  • Barbecue
  • Deck or patio

Explore the area

View map
Chestertown, MD
  • Place, Wilmer Park
    ‪5 min drive‬
  • Place, River Arts Chestertown
    ‪5 min drive‬
  • Place, Chestertown Historic District
    ‪5 min drive‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪131 min drive‬

Rooms & beds

1 bedroom (sleeps 3)

Bedroom 1

1 Queen Bed and 1 Double Futon

1 bathroom

Bathroom 1

Shower only

Spaces

Deck or patio
Outdoor play area

About this property

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*

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House Rules

Check in after 4:00 PM
Minimum age to rent: 20
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
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.

Important information

You need to know

Property Registration Number 025962
Property # 2677763vb
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

Located in Chestertown, this apartment is in a rural area and next to a golf course. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Wilmer Park. Garfield Center for the Arts at the Prince Theater 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 hiking and ecotours nearby.
View more Apartments in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • Wilmer Park - 5 min drive - 3.8 km
  • River Arts Chestertown - 5 min drive - 4.5 km
  • Chestertown Historic District - 5 min drive - 4.9 km
  • Historical Society of Kent County Maryland - 5 min drive - 4.9 km
  • Washington College - 6 min drive - 5.5 km

Getting around

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

Restaurants

  • ‪Milano's Pizzeria - ‬8 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪Dunkin - ‬6 min drive
  • ‪Procolino's - ‬6 min drive
  • ‪Royal Farms - ‬7 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 17 June 2026, prices found for a 1-night stay for 2 adults at First Floor Studio Apartment in Historic Chestertown on 23 June 2026 start from NZ$278, 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 First Floor Studio Apartment in Historic Chestertown pet-friendly?

No, pets are not allowed at this property.

How much is parking at First Floor Studio Apartment in Historic Chestertown?

On-site 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?

Checkout 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 miles (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 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 96 out of 113 reviews
Rating 8 - Good. 13 out of 113 reviews
Rating 6 - Okay. 2 out of 113 reviews
Rating 4 - Poor. 2 out of 113 reviews
Rating 2 - Terrible. 0 out of 113 reviews

9.8/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified

10/10 Excellent

John R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
A beautiful and comfortable accomodations.
Stayed 1 night in Jun 2026
Verified

10/10 Excellent

S G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Exactly as advertised. Great room, clean and highly recommended.
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

Lisa v.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely stay at Elisabeths place. She helped us with anything we needed. The aprtment was clean, cozy and just right for 2 people.
Stayed 3 nights in Mar 2026
Verified

10/10 Excellent

Rob C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Hosts were extremely friendly and helpful!Parking was within feet of entrance. Studio and bathroom were spotless. Nice touches like coffee and accoutrements in the shower. Beautiful surroundings, everything was in bloom and spring beauty was everywhere!Washer and dryer in studio with soap and softener. Charming location!
Stayed 2 nights in Apr 2026
Verified

10/10 Excellent

lesia k.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Every thing was great
Stayed 3 nights in Nov 2025
Verified

10/10 Excellent

Anne D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely visit. It was nice and quiet and parking was perfect.
Stayed 5 nights in Sep 2025
Verified

10/10 Excellent

Iriana J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was clean and neat and welcoming
Stayed 1 night in Nov 2025
Verified

10/10 Excellent

Cecily L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, comfortable accessible, and very responsive owner. Highly recommend :-)
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

SoYoung L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very comfortable and clean. Shower pressure is excellent!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Firoze R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location, excellent communication. Served the purpose very well.
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Alexander M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing and neat and very private
Stayed 1 night in Aug 2025
Verified

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
Verified

10/10 Excellent

Lisa O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful, spacious, and clean!
Stayed 1 night in Aug 2025
Verified

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
Verified

10/10 Excellent

Sandra S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful property, immaculately kept in lovely neighborhood. Responsive and thoughtful host!
Stayed 1 night in Sep 2025
Verified

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
Verified

10/10 Excellent

Stephanie T.

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

Most amazing place!

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

10/10 Excellent

Amber A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The space was super cute and cozy! So close to town, which was AMAZING!! The owners were readily available, if I needed anything or had any questions. I will definitely be back!
Stayed 2 nights in Aug 2025
Verified

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
Verified

8/10 Good

Cheryl W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and welcoming. We would have liked plates/utensils to heat up our breakfast food. We also would have loved to meet our hosts! Especially after we discovered that our granddaughter and their daughter were friends in the same class. Small world. The location near the school was optimal.
Stayed 1 night in Nov 2025
Response from VrboOwner on 28 November 2025
Such a small world! We learned our parents stayed at the same hotel as you for Grandfriend's Day last year. We do have plates, extra cups, utensils, tea, a few single serve condiments, any spare toiletries you could think of, in the blue dresser, under the TV. We hope that you stay with us next time you are in Chestertown!
Verified

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
Verified

8/10 Good

judith v.

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

Outing with a grandchild

All was excellent. I do prefer a firmer mattress though - my only downside to our visit.
Stayed 2 nights in Aug 2025
Verified

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
Verified

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
Verified

10/10 Excellent

Deborah P.

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

Wonderful weekend

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

About the host

Hosted by Elisabeth Cunningham

Host profile image
We are a family of 5, looking to share our quite sanctuary! We strive to offer our guests a clean, affordable place to relax, while exploring Chestertown.

Why they chose this property

This property has large doorways, shower/toilet grab rails and smooth, level flooring. There are 4 stairs to enter this property, with rails on either side. Please let us know how we can make your stay most enjoyable!

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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