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Historic Downtown Garden Oasis with Private Patio

Photo gallery for Historic Downtown Garden Oasis with Private Patio

Outdoor dining
Living area
Interior
Private kitchen
Room

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 2

Popular amenities

  • Onsite parking available
  • Kitchenette
  • Air-conditioning
  • Barbecue
  • Balcony or patio
  • Free Wi-Fi

Explore the area

View map
Chestertown, MD
  • Place, River Arts Chestertown
    ‪3 min walk‬
  • Place, Historical Society of Kent County Maryland
    ‪8 min walk‬
  • Place, Washington College
    ‪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

About this property

Historic Downtown Garden Oasis with Private Patio

Welcome to 108Annex, your ideal Chesapeake Bay retreat! Nestled in historic downtown Chestertown, our one-bedroom guesthouse is the perfect place for couples or solo travelers to enjoy a long relaxing weekend. Just steps away from downtown restaurants, cafes, and shops, you'll be able to explore all the Arts & Entertainment District has to offer. We look forward to hosting you!

Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill.

We are proud to give back to our town through the renting of our guesthouse. Five percent of our gross revenue is donated to one or more local non-profits annually. Additionally, the guesthouse features artwork from local artists and galleries, and you'll find home goods and products from nearby shops.

Our place is designed to provide you with everything you need for a comfortable stay, including fast wifi, a private entrance with self check-in via keyless entry, and free street or off-street parking.

You'll find all the essentials like towels, bed sheets, soap, and toilet paper, as well as a hairdryer, cleaning products, shampoo, conditioner, and body soap. There are extra pillows and blankets, and hangers to store your clothes.

The guesthouse has two brand new air conditioning and heating units that you control, so you will be comfortable year-round.

Safety is a top priority, so we have a smoke and carbon monoxide alarm, a fire extinguisher, and a first aid kit on hand. Additionally, for awareness, there is a Ring Video Doorbell installed on the front door of the primary house. It is used to monitor our front door but not the door of the guest unit.

In the kitchenette, you'll find a microwave, dishes, silverware, cups, a mini-fridge with freezer, a hot water kettle, a coffee maker (both a Keurig and a Nespresso), wine glasses, and a toaster.

During your stay you will have exclusive access to the following rooms and spaces:

- Bedroom
- Full bathroom
- Kitchenette
- Living room
- Dining area
- Patio

Additionally, you'll be sharing the backyard with us, but we'll do our best to give you privacy during your stay.

If you have any questions or concerns about the areas you can access, or if you need any additional information about your stay, please don't hesitate to ask.

We're committed to providing our guests with an exceptional experience, and we're always available to answer any questions or provide recommendations to help make your stay unforgettable.

Here's what some of our recent guests have said about their stay:

"Perfect apartment-type accommodation located in a lovely walkable town. These hosts literally thought of a guest's every need... Besides being a comfortable, beautiful space top to bottom with an abundance of windows, the things that really stood out for us are: Self-check in keyless entry, gallery artwork throughout; large stone-top table with chairs for eating, gathering, working, etc; coffee machine with Keurig AND Nespresso pods (WOW!)" - Cindy

"Their place was exactly what I was looking for! It was clean, cute, centrally located, but yet private and offered everything I needed for my stay! I loved the special touches from the local businesses, the espressos, coffee, and tea options. Their place was spotless and the bed was extremely comfortable! They were also very responsive with any questions I had. If I ever come back to the area I will definitely stay at their place." - Megan

"Great place and location. Private and quiet, but walkable to restaurants of Chestertown. Comfortable and super clean! Very cute, indoors and out." - Joan

"Stephen and Marianna were delightful hosts for a perfect getaway weekend in Chestertown! Their detailed suggestions of local restaurants and events made our stay more enjoyable, as were their thoughtful messages to us during our stay to ensure that everything was going well. The apartment is such a gem tucked away in a courtyard at the back of their house in the historical section of town!" - Carla

We're confident that you'll love your stay at our guesthouse, and we can't wait to welcome you.

Book now to secure your spot!

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
While not child friendly, we can accommodate.
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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

Check-out instructions

The host requires you to complete the following before checking out:
Remove personal items and remove leftover food and drinks
Turn off the lights and lock the doors
Failure to complete these may result in a negative review from the host.
There is a maximum stay of one month for Instant Bookings. For longer stays, please message the host first. Otherwise, your booking may be cancelled.
The max number of guests is two people. If you are two adults traveling with a child under 5, we can accommodate but you must let us know at booking.

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, a first aid kit and a deadlock

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 Larrabee Arts Center. Crumpton Auction and The Mainstay 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 ecotours and cycling nearby.
View more Apartments in ChestertownOpens in a new window
Map
Chestertown, MD

What's nearby

  • River Arts Chestertown - 3 min walk - 0.3 km
  • Garfield Center for the Arts at the Prince Theater - 6 min walk - 0.6 km
  • Historical Society of Kent County Maryland - 8 min walk - 0.7 km
  • Washington College - 8 min walk - 0.7 km
  • Wilmer Park - 8 min walk - 0.7 km

Getting around

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

Restaurants

  • ‪Milano's Pizzeria - ‬4 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Dunkin - ‬3 min drive
  • ‪Royal Farms - ‬4 min drive
  • ‪Procolino's - ‬3 min drive

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Historic Downtown Garden Oasis with Private Patio?

As of 6 May 2026, prices found for a 1-night stay for 2 adults at Historic Downtown Garden Oasis with Private Patio on 31 August 2026 start from NZ$344, 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.

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 10-minute walk of River Arts Chestertown, Garfield Center for the Arts at the Prince Theater and Sumner Hall. Historical Society of Kent County Maryland and Chestertown Historic District 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. 47 out of 49 reviews
Rating 8 - Good. 2 out of 49 reviews
Rating 6 - Okay. 0 out of 49 reviews
Rating 4 - Poor. 0 out of 49 reviews
Rating 2 - Terrible. 0 out of 49 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

10/10 Excellent

Kevin H.

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

10/10 Excellent

David H.

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

10/10 Excellent

Vanessa S.

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

10/10 Excellent

Michele R.

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

10/10 Excellent

Devan G.

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

8/10 Good

Cynthia S.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Christina S.

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

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect quaint property! everything you would need provided except we didn’t realize there was no TV but that was us not the property. Highly recommend. great location. walk to everything Chestertown.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

June M.

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

10/10 Excellent

Mary Pat

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

10/10 Excellent

kathleen d.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This is a charming place. Beautifully furnished with no detail overlooked. We loved the artwork by local artists, the attention to sustainability, and the commitment to the community. The location was perfect - a few minutes walk to the shops and restaurants and the Saturday farmers' market. One of the best we had ever visited!Communications with the owners and check-in were smooth. We hope to return.
Stayed 2 nights in Sep 2025
Verified

10/10 Excellent

Lindsey C.

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

10/10 Excellent

Susan H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very neat and clean. Quiet and private. Short walk to shopping and restaurants. Quick response from host when questions or recommendations were asked. No TV encouraged us to enjoy the outdoors.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

alex d.

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

10/10 Excellent

Verified traveller

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

10/10 Excellent

Amanda D.

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

Nice place to stay!

Very nice little apartment with a separate entrance from the main house. It was furnished and decorated very nicely (it didn't feel like a generic rental but it wasn't so fancy you were afraid to use stuff). Comfortable bed, nice pillows, nice sheets. I loved the porch and garden (and occasional visits from their very cute dog).
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Tiffany c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
As others have noted, the space is very clean, well appointed and conveniently located. I'd like to add that the hosts have done a wonderful job of representing the community in the home. Their art collection is lovely and features local artists. The books placed are all interesting and about the area; even the chocolates were purchased from a locally owned store. I would absolutely stay here again and highly recommend it.
Stayed 5 nights in Jul 2025
Verified

10/10 Excellent

Julia D.

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

10/10 Excellent

June M.

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

10/10 Excellent

Judy C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Only wonderful things to say about this sweet apartment. First, the hosts, Stephen and Mariana, are incredibly hospitable and full of great ideas and recommendations for the area. This property is very clean and roomy (for two), has wonderful amenities and the hosts have thought of everything that makes this our go to place to stay when we are in Chestertown. This property is in a historic area, an easy walk to the river, the historic district, shops, a nature center, park, and many restaurants. It is an easy drive to anywhere requiring a car and parking is available and convenient. We highly recommend!
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

henny m.

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

10/10 Excellent

JOSE F.

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

10/10 Excellent

John L.

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

10/10 Excellent

Brian W.

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

Immaculate and charming space!

Weekend stay from Philly. Everything was perfect for the two of us. The space is so inviting with a beautiful outdoor garden and sitting area. Quiet, impeccably maintained and stocked with every detail that we needed. Outstanding hosts. Can’t wait to visit Charlestown annd stay here again!
Stayed 2 nights in May 2025

About the host

Hosted by Stephen M Massoni

Host profile image
My partner, Marianna, and I are former Brooklynites now living the good life in Chestertown, MD. We love to travel, especially to Italy, and enjoy the way vacation rentals give you a more authentic feel of a city or place. We hope to host you or be hosted by you in the near future.

Why they chose this property

Welcome to Chestertown, Maryland – a charming and historic town nestled along the banks of the Chester River. With its quaint streets lined with beautiful colonial architecture and stunning waterfront views, Chestertown is the perfect destination for those seeking a peaceful and picturesque getaway. In Chestertown, there's something for everyone. Founded in 1706, history buffs can explore the town's rich heritage through its many historic sites and museums, while nature lovers can enjoy the scenic beauty of the Chester River and nearby parks and wildlife preserves. Foodies will delight in the town's vibrant culinary scene, which features everything from traditional Maryland crab cakes to farm-to-table cuisine made with locally sourced ingredients. But perhaps the best thing about Chestertown is its sense of community. Whether you're strolling through the town's farmer's market, attending one of its many festivals and events, or simply chatting with the friendly locals, you'll feel right at home in this welcoming and vibrant town.

What makes this property unique

Our guesthouse is a two-floor 525 sqft unit with a queen bedroom and en suite bathroom upstairs, and a living room with dining/working area and kitchenette downstairs. You'll love the private patio space, which offers separate seating and dining areas with beautiful views of our garden and access to the fully-fenced backyard and grill. We are proud to showcase local artists and businesses in our space. The guesthouse features artwork from local galleries, and you'll find home goods and products from nearby shops.

Languages:

English

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