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Historic Downtown Garden Oasis with Private Patio

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Property grounds
Fridge, microwave, coffee/tea maker, electric kettle
Terrace/patio
1 bedroom, free WiFi, bed sheets
Interior

Reviews

10 out of 10
Exceptional

Entire apartment

1 bedroom1 bathroomSleeps 2

Popular amenities

  • Parking available
  • Barbecue grill
  • Outdoor Space
  • Kitchen
  • Free WiFi
  • Air conditioning

Explore the area

Map
Chestertown, MD
  • River Arts Chestertown
    ‪3 min walk‬
  • Historical Society of Kent County Maryland
    ‪8 min walk‬
  • Washington College
    ‪8 min walk‬
  • Easton, MD (ESN-Easton - Newnam)
    ‪58 min drive‬

Room options

About the neighborhood

Chestertown

Heart of Chestertown.At this apartment, you'll be steps from River Arts Chestertown and within a 10-minute walk of Garfield Center for the Arts at the Prince Theater. Sumner Hall and Historical Society of Kent County Maryland are also within half a mile (1 km).
View more Apartments in ChestertownOpens in a new window

What's nearby

  • River Arts Chestertown - 3 min walk - 0.2 miles
  • Wilmer Park - 6 min walk - 0.4 miles
  • Garfield Center for the Arts at the Prince Theater - 6 min walk - 0.4 miles
  • Historical Society of Kent County Maryland - 8 min walk - 0.5 miles
  • Washington College - 8 min walk - 0.5 miles

Getting around

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

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Dining Hall - ‬13 min walk
  • ‪Procolino Pizza - ‬3 min drive
  • ‪China House - ‬3 min drive
  • ‪The Freeze - ‬3 min drive

About this property

Entire place

You'll have the entire apartment to yourself and will only share it with other guests in your party.

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.

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!

Property manager

Stephen M Massoni

Languages

English

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Property amenities

Internet

  • Available in the apartment: Free WiFi

Parking and transportation

  • Free offsite parking
  • Onsite parking includes off-street options

Kitchenette

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Freezer
  • Microwave
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 private bathroom
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room
  • Separate dining area

Entertainment

  • Books
  • Stereo

Outdoor areas

  • Barbecue grill
  • Fenced yard
  • Fully-fenced
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundromat nearby

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Location highlights

  • In a rural location
  • In the city center
  • Near a hospital

Things to do

  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing 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
  • Deadbolt lock

General

  • Garden
  • Local artist showcase

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

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

Check-out instructions

The host requires you complete the following before checking out:
Remove personal items and remove leftover food and drinks
Turn off the lights and lock the doors

Access methods

Private entrance

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Note from host: While not child friendly, we can accommodate.

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, a first aid kit, and a deadbolt lock
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Frequently asked questions

How close is Historic Downtown Garden Oasis with Private Patio to the airport?

This apartment is 78.9 mi (93-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

Does Historic Downtown Garden Oasis with Private Patio have an airport shuttle?

Airport shuttle services are not available at this apartment.

How close is Historic Downtown Garden Oasis with Private Patio to the beach?

This apartment is 13.1 mi (25-min drive) from Betterton Beach and 13.7 mi (26-min drive) from Main Beach. Don't forget your sunscreen!

Does Historic Downtown Garden Oasis with Private Patio offer free breakfast?

This apartment does not offer free breakfast.

Is there a casino at Historic Downtown Garden Oasis with Private Patio?

No, there is no casino at this apartment.

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

Check-in begins at 3:00 PM.

Is there free parking at Historic Downtown Garden Oasis with Private Patio?

Free parking is not available at this apartment.

Does Historic Downtown Garden Oasis with Private Patio have a pool?

This apartment does not have a pool.

Does Historic Downtown Garden Oasis with Private Patio have a spa?

There are no spa services available at this apartment.

How close is Historic Downtown Garden Oasis with Private Patio to downtown Chestertown?

This apartment is 0.6 mi away from Chestertown.

Historic Downtown Garden Oasis with Private Patio Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 31 out of 31 reviews
Rating 8 - Good. 0 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 0 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness

Reviews

10/10 Excellent

Brian W.

Liked: Cleanliness

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

10/10 Excellent

Verified traveler

Liked: Cleanliness

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

10/10 Excellent

Lindsey C.

Liked: Cleanliness

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

10/10 Excellent

June M.

Liked: Cleanliness

Quite nice!

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

10/10 Excellent

Tammy S.

Liked: Cleanliness

Perfect little gem in the heart of Chestertown

We loved staying at Stephen and Marianna’s fantastic home. The space is bright and well-decorated, it’s private and had all of the amenities we needed. The location is wonderful and we were able to walk a couple of blocks to the stores and restaurants and enjoyed the Saturday morning farmers market. When we checked in, the keypad wasn’t working but within about a minute, Stephen appeared and let us in so it was all very easy and nice. Highly recommend staying here - perfect for a couple to do a weekend getaway!
Stayed 2 nights in Mar 2025

10/10 Excellent

Hillary K.

Stayed 7 nights in Oct 2024

10/10 Excellent

Karen W.

Liked: Cleanliness

Perfection - you won't want to leave

This is the second time I stayed here and will be back. I was able to work from here and enjoyed breakfast and lunch on the covered porch with a sweet companion (the owners' totally chill dog). Walking distance to everything. Check out the new wetland preserve at the end of the street.
Stayed 3 nights in Nov 2024

10/10 Excellent

Mary Pat

Liked: Cleanliness, property conditions & facilities
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

10/10 Excellent

Julia D.

Liked: Cleanliness

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

10/10 Excellent

June M.

Liked: Cleanliness

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

10/10 Excellent

alex d.

Liked: Cleanliness

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

10/10 Excellent

James B.

Liked: Cleanliness

Great trip to Chestertown

Short stay to move our child in to college. Our hosts were exceptional. The stay had everything you could want and the communication was great. We will definitely be back.
Stayed 2 nights in Aug 2024

10/10 Excellent

Mary H.

Liked: Cleanliness

Perfect little gem

This is a lovely little place within walking distance to great restaurants, shops and points of interest. Our hosts were pleasant and available and gave us good recommendations for where to eat. This truly is a garden oasis outside. I sat with my coffee and wrote in my journal each morning on the patio. The inside is perfectly appointed with anything we needed and is super clean. We hope to return in the future!
Stayed 2 nights in Aug 2024

10/10 Excellent

andrew k.

Liked: Cleanliness

Quaint, quiet and safe!

What an awesome stay in Chestertown! We loved the little house that we rented! The owners of the property were very receptive and gave advice for dining options. The property was in walking distance of all restaurants, shopping and attractions. We would definitely stay again. Thank you!
Stayed 3 nights in Jul 2024

10/10 Excellent

JOSE F.

Liked: Cleanliness

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

10/10 Excellent

Danielle, Claremont

Traveled with partner
Liked: Cleanliness, amenities, property conditions & facilities
A perfect stay in lovely, comfortable private guest quarters. Perfect for a couple. Well designed layout. Kitchen includes a toaster oven, microwave and coffee machine (capsules provided). Extremely well located, close to the superb Watershed Alley and Modern Stone Age Kitchen as well as the brand new Lawrence Wetlands Preserve (ideal if you are a birder!). Will definitely return to enjoy Stephen's and Marianna's guest suite.
Stayed 3 nights in May 2024

10/10 Excellent

Christopher B., Timnath, CO

Liked: Cleanliness

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

10/10 Excellent

Karen W.

Liked: Cleanliness

Great space for my last minute stay

I reserved the space the day before and the hosts were very accommodating. The space was very comfortable with a great table and reliable WiFi for me to work. Garden is beautiful! Wish I could've stayed longer.
Stayed 2 nights in Apr 2024

10/10 Excellent

Philip B.

Liked: Cleanliness

Chestertown Christmas

The location is wonderful. Very close to all the going on in Chestertown. We could easily walk to restaurants and shops. The unit was very comfortable and the host were exceptionally nice.
Stayed 6 nights in Dec 2023

10/10 Excellent

Jay Y.

Liked: Cleanliness

So thankful

I was so thankful to find this wonderful place to stay for my brother and his friend so they could comfortably visit for Thanksgiving. They said over and over how comfortable and clean everything was!
Stayed 2 nights in Nov 2023

10/10 Excellent

Karen G., Gettysburg, PA

Liked: Cleanliness

Great Location!

As a frequent visitor to Chestertown, I loved this location - walkable to everywhere in town and to the college as well. Very comfortable for 2 people and has a small fridge & sink and all the basic necessities you'll need for your stay! And quiet too, just off the main street through town. Check in easy / communication with host excellent! I will be back again another day!
Stayed 4 nights in Oct 2023

10/10 Excellent

John L.

Liked: Cleanliness

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

10/10 Excellent

Judy C.

Liked: Cleanliness

Lovely and comfortable apartment close to town

Stephen and Mariana could not have made their accommodation any more comfortable. Everything we could have needed was there. The bedroom was spacious and the bathroom very nicely laid out. We used the kitchen area in the morning for coffee, keep and eat snacks, chill water, milk, beer, and wine, and eat take-out. The living/dining area so comfortable and the porch was perfect to sit out on even during the rain showers. Their house is an easy walk to downtown Chestertown. Mariana gave us several recommendations for shops, restaurants, and other activities. Plenty of parking on the street. They are the nicest couple and I can't speak highly enough of their hospitality and accommodations.
Stayed 3 nights in Sep 2023

10/10 Excellent

Linda Carol K.

Liked: Cleanliness

Great Location

The apartment is in a great location, a short walk to all the goings on in Chestertown, but it is still very quiet and situated in a private courtyard. The bedroom and bathroom are located on the second floor, but this was not a problem for us. We would definitely stay there again.
Stayed 3 nights in Sep 2023

10/10 Excellent

Christina S.

Liked: Cleanliness

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