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First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown with fitness centre and outdoor pool

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
1 bedroom1 bathroomSleeps 3

Popular amenities

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

Explore the area

View map
  • Place, River Arts Chestertown
  • Place, Washington College
  • Place, Rolphs Wharf Marina
  • Airport, Easton, MD (ESN-Easton - Newnam)

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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Amenities

Pool
Hot tub
Washing machine
Dryer
Free WiFi
Air conditioning

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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

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
Property Registration Number 025962

About the area

Chestertown

Located in Chestertown, this apartment is in a rural area and next to a golf course. The area's natural beauty can be seen at Wilmer Park and Chestertown Historic District, while Sumner Hall and Garfield Center for the Arts at the Prince Theater are cultural highlights. Crumpton Auction and Hazel Miner Monument are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Chestertown, MD

What's nearby

  • Wilmer Park - 3 min drive - 2.8 km
  • River Arts Chestertown - 4 min drive - 3.5 km
  • Historical Society of Kent County Maryland - 4 min drive - 3.5 km
  • Washington College - 5 min drive - 4.2 km
  • Rolphs Wharf Marina - 14 min drive - 12.5 km

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 9 Nov 2025, prices found for a 1-night stay for 2 adults at First Floor Studio Apartment in Historic Chestertown on 10 Nov 2025 start from AU$213.84, 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.

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

9.8/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

9.4/10

Eco-friendliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy
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

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

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

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

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

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

Judy S.

Liked: Cleanliness, check-in, communication, listing accuracy
The property was beautiful and our accommodations were wonderful. The only issue we had was nothing to do with this property. It was not easily accessible to town by foot. We went to the Chestertown Community page and asked about Uber accessibility and were told 24/7. We came to Chestertown by boat, no vehicle. We had a 2 mile walk to town to get something to eat.
Stayed 1 night in Aug 2025

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

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

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

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

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

10/10 Excellent

Lisa O.

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

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

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