Historic Downtown Garden Oasis with Private Patio

Photo gallery for Historic Downtown Garden Oasis with Private Patio

A covered patio with a brick floor, wooden chairs, and a table set for dining.
A staircase with wooden steps leading to a landing.
A kitchen with white shelves holding glassware and dishes, a coffee maker, and a wine bottle on the counter.
A neatly made bed with a white quilt, a bedside table with a lamp, books, and a glass bottle.
A modern kitchen with dark cabinets, a white countertop, and a window with pink blinds.

Reviews

10 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Private fenced-in yard
    One of the few properties with a fully fenced outdoor space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Washington College

Popular amenities

  • Balcony or patio
  • Kitchenette
  • Barbecue grill
  • Free Wi-Fi in public areas
  • Air-conditioning
  • Refrigerator

Explore the area

View in a map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪3 min walk‬
  • Place, Washington College
    ‪8 min walk‬
  • Place, Chestertown Historic District
    ‪8 min walk‬
  • Airport, Baltimore, MD (MTN-Martin State)
    ‪126 min drive‬

Rooms & beds

1 bedroom (sleeps 2)

Bedroom

1 Queen Bed

1 bathroom

Bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchenette
Separate dining area
Garden
Dining area

Add dates for prices

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About the area

Chestertown

Located in Chestertown, this apartment is in the city centre. Historical Society of Kent County Maryland and Betterton Historic District are local landmarks, and some of the area's attractions include Garfield Center for the Arts at the Prince Theater and Schooner Sultana. Larrabee Arts Center and Crumpton Auction are also worth visiting. Kayaking and power boating offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling and ecotours nearby.
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Map
Chestertown, MD

What's nearby

  • River Arts Chestertown - 3 min walk - 0.3 km
  • Historical Society of Kent County Maryland - 8 min walk - 0.7 km
  • Washington College - 8 min walk - 0.7 km
  • Chestertown Historic District - 8 min walk - 0.7 km
  • Sumner Hall - 8 min walk - 0.7 km

Getting around

  • Baltimore, MD (MTN-Martin State) - 93 min drive

Restaurants

  • ‪Royal Farms - ‬4 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin - ‬3 min drive
  • ‪Procolino's - ‬3 min drive
  • ‪Royal Farms - ‬6 min walk

Frequently asked questions

Is Historic Downtown Garden Oasis with Private Patio pet-friendly?

No, pets are not allowed at this property.

How much is parking at Historic Downtown Garden Oasis with Private Patio?

There is free parking nearby.

What time is check-in at Historic Downtown Garden Oasis with Private Patio?

Check-in begins at 3:00 PM.

What time is check-out at Historic Downtown Garden Oasis with Private Patio?

Checkout is at 11:00 AM.

Where is Historic Downtown Garden Oasis with Private Patio located?

Located in the heart of Chestertown, this apartment building is within a 5-minute walk of Chestertown Farmers Market, River Arts Chestertown and Schooner Sultana. Garfield Center for the Arts at the Prince Theater and Sumner Hall are also within 10 minutes.

Reviews

10

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. 57 out of 59 reviews
Rating 8 - Good. 2 out of 59 reviews
Rating 6 - Okay. 0 out of 59 reviews
Rating 4 - Poor. 0 out of 59 reviews
Rating 2 - Terrible. 0 out of 59 reviews

10/10

Cleanliness

9.6/10

Amenities

9.8/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great small place close to all the local places to shop and eat in a quaint little town!!!!
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, clean and very comfortable quarters. Wonderful stay!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location is fabulous and only one block from downtown historical district. Everything was spotless. The kitchen space is super tiny which made it a bit difficult because I am GF and Vegan and the restaurants have little to offer. Otherwise its the perfect spot to be in Chestertown.
Stayed 3 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The stay was incredible! We had an amazing weekend and definitely plan to return when we’re back in town!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely apartment- wonderful porch overlooking a beautiful garden.Perfect amenities-lovely stay
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful weekend in Chestertown - perfect location!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful location and amenities! Hosts were helpful and informative
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
I can’t tell you how lovely our stay was because of this beautiful home. The set up is terrific. And we really admire your choice of art. We also enjoyed ourselves last night sitting on the porch. Your yard is so peaceful and lush. You provided us with a clean, charming, comfortable home away from home. Thank you.
Stayed 3 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the location and ease of access to downtown. Property was super clean, organized and beautifully appointed with original art too.
Stayed 2 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, location
Important to know the bedroom is upstairs which I didn't remember in the description. Space is lovely. Beautiful back yard to enjoy with wine and cheese. Nice hosts. A TV would have made it complete but we managed with a tablet.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

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

Wonderful weekend getaway

We had a very enjoyable weekend at this property. The owners were super friendly and helpful! We would definitely stay here again when visiting the area.
Stayed 2 nights in Aug 2023
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond.
Stayed 2 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was perfect and cozy. Stephen and Marianna are wonderful hosts and have anticipated all of our needs yet again. Their rental is inviting and beautifully appointed.
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We thoroughly enjoyed our stay at this property. The location was superb. We were able to spend the day in town with never having to drive anywhere. Chestertown was charming and unique and this rental went right along with that. Other favorites were the outside area, the layout and coziness of the rental. You will not be disappointed if you chose this as your rental for your Chestertown stay!
Stayed 2 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities, communication
The cottage was comfortable and welcoming. It was close to restaurants, the Farmers' Market and delightful shops and galleries.
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

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

Quite nice!

Property is clean & comfortable. Great location for walking to downtown Chestertown shopping and restaurants.
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

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

Amazing experience

We had such a sweet & relaxing stay at this garden oasis. It was equipped with everything we needed and we cannot wait to be back.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

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

Wonderful stay!! Great hosts.

This was the perfect place for my week in town visiting my elderly father. The location is perfect and the accommodations are charming, comfortable, tasteful, well kept, and clean. Couldn’t ask for better. I will definitely hope to stay again soon when I return.
Stayed 6 nights in Jun 2023
Verified review

10/10 Excellent

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

Our stay for War on the Shore

Your guest house was perfect. It had everything we needed. Short walk to town and the Chester River. Will definitely book again when we come to town for our son’s lacrosse games!
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

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

Sweet serene spot in the heart of Chestertown!

We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

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

Perfect place!

This property was so accessible to everything we wanted to do and the accommodations perfect for the two of us. It was like a home away from home comfortable and clean! Even the pillows were perfect! We would highly recommend.
Stayed 2 nights in Sep 2024
Verified review

10/10 Excellent

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

Great spot in Chestertown

We had a wonderful weekend in Chestertown at this property. It is centrally located to both restaurants and shopping. Additionally the host was terribly polite and agreeable.
Stayed 2 nights in Oct 2023
Verified review

10/10 Excellent

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

Great chill stay

Stephen & Marianna were great hosts! They gave recommendations for what was nearby for food and drinks and made us feel at home. the space was great and sitting on the patio was very pleasant. They are centrally located so it was very easy to park the car and walk to the main downtown. Would 100% stay again!
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

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

Anniversary in Chestertown

Wonderful selection in Maryland Historic Cities circuit as well as in Scenic Routes on the MD Eastern Shore.
Stayed 4 nights in Jul 2024
Verified review

10/10 Excellent

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

Great Chestertown location

Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit.
Stayed 3 nights in May 2024
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