Title: Historic Downtown Garden Oasis with Private Patio - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire apartment # Historic Downtown Garden Oasis with Private Patio Apartment in Chestertown with kitchenette and balcony ![Property grounds](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/d1ca16e3.jpg?impolicy=resizecrop&rw=598&ra=fit) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/e71a8b70.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/dc0d7c61.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/b30cfa2a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/1fa2457a.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Nestled in historic downtown Chestertown, 108Annex is the perfect retreat for couples or solo travelers. This cozy one-bedroom guesthouse features a private patio space with beautiful views of the garden and access to the fully-fenced backyard and grill. 10 Exceptional ### Entire apartment 1 bedroom1 bathroomSleeps 2525 sq ft ## Popular amenities - - Parking available - Barbecue grill - Kitchen - Outdoor space - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## 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. 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! ## 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 - Smoking not allowed ### 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 - Unit size: 525 square feet ## Similar properties ![Property grounds](https://images.trvl-media.com/lodging/76000000/75860000/75854900/75854900/04bd524d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### First Floor Studio Apartment in Historic Chestertown Chestertown - Pool - Hot tub - Washer - Dryer 9.6 Exceptional 107 reviews CA $138 CA $222 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-01&endDate=2025-12-02&selected=75854900&PinnedHotelID=75854900&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90880000/90876100/90876079/fc8d3076.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Newly restored apartment in the heart of Chestertown Chestertown - Kitchen - Washer - Dryer - Free WiFi 9.8 Exceptional 27 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&selected=90876079&PinnedHotelID=90876079&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118140000/118131300/118131300/w1075h1080x5y0-d2ed6db8.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access Chestertown - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&selected=118131300&PinnedHotelID=118131300&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/104000000/103190000/103180100/103180013/6b42c6a9.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Waterfront Retreat with Private Dock and Beach Worton - Kitchen - Free WiFi - Air conditioning - Parking available 10 Exceptional 25 reviews CA $245 CA $435 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-01&endDate=2025-12-02&selected=103180013&PinnedHotelID=103180013&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66473100/66473084/e3526265.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Circa 1900 Home in the Heart of Historic Downtown Chestertown Chestertown - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 76 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&selected=66473084&PinnedHotelID=66473084&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/55000000/54850000/54841100/54841025/e626cb61.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Country Estate in Historic District Chestertown - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 70 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15&selected=54841025&PinnedHotelID=54841025&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/114000000/113420000/113417900/113417810/1d961d4b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Outrange at Blue Heron Farm. 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Within 2 Blocks of Fountain Park!! 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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. ### Access methods Private entrance ### Pets Pets not allowed ### Children and extra beds Children are welcome Note from host: While not child friendly, we can accommodate. ### Events No events allowed ### Smoking Smoking is not permitted ## 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 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C39.21002%2C-76.06913&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=sa3i9I1VJA4pnZWFldP-QBF7tk4=) Chestertown, MD #### What's nearby - River Arts Chestertown - 3 min walk - 0.3 km - Wilmer Park - 6 min walk - 0.6 km - Washington College - 8 min walk - 0.7 km - Historical Society of Kent County Maryland - 8 min walk - 0.7 km - Chestertown Historic District - 8 min walk - 0.7 km #### Getting around - Baltimore, MD (MTN-Martin State) - 93 min drive #### Restaurants - ‪Royal Farms - ‬6 min walk - ‪McDonald's - ‬3 min drive - ‪Dunkin - ‬3 min drive - ‪Procolino's - ‬3 min drive - ‪Subway - ‬18 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? > 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? > Check-out 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. ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Historic Downtown Garden Oasis with Private Patio Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) ### 10 Cleanliness ### 10 Location ### 9.4 Eco-friendliness ### 9.8 Property conditions & facilities 10 - Excellent 41 8 - Good 2 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Excellent #### Michele R. Aug 31, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Wonderful weekend in Chestertown - perfect location! ##### Michele R. Stayed 2 nights in Aug 2025 ### 8/10 Good #### Cynthia S. Jun 8, 2025 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. ##### Cynthia S. Stayed 2 nights in Jun 2025 ### 10/10 Excellent #### Verified traveller Jul 5, 2025 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. ##### Verified traveller Stayed 2 nights in Jul 2025 ### 10/10 Excellent #### June M. Apr 19, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Quite nice! Property is clean & comfortable. Great location for walking to downtown Chestertown shopping and restaurants. ##### June M. Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Tiffany c. Jul 29, 2025 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. ##### Tiffany c. Stayed 5 nights in Jul 2025 ### 10/10 Excellent #### Lindsey C. Apr 27, 2025 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! ##### Lindsey C. Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Amanda D. Jun 1, 2025 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). ##### Amanda D. Stayed 2 nights in May 2025 ### 10/10 Excellent #### Verified traveller Apr 30, 2025 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! ##### Verified traveller Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Mary Pat Oct 14, 2024 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. ##### Mary Pat Stayed 2 nights in Oct 2024 ### 10/10 Excellent #### Christina S. Aug 7, 2023 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. ##### Christina S. Stayed 2 nights in Aug 2023 ### 10/10 Excellent #### Brian W. May 11, 2025 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! ##### Brian W. Stayed 2 nights in May 2025 ### 8/10 Good #### Carlos Jun 3, 2025 Liked: Cleanliness, amenities, property conditions & facilities, communication Very quiet area and well kept properly. The unit very clean and well kept, the Internet is pretty good with good reception, what I like the most was that it was so close to everything with restaurants and museums close by the park that hosted most of the events was close enough for a short walk and all sort of streets that held events were close by, this is a great location of the memorial day events and I have to say the honest were great and very helpful. ##### Carlos Stayed 3 nights in May 2025 ### 10/10 Excellent #### alex d. Aug 25, 2024 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. ##### alex d. Stayed 2 nights in Aug 2024 ### 10/10 Excellent #### George May 5, 2025 Liked: Cleanliness, amenities, property conditions & facilities, communication Very nice place. Great location, close to dining, etc. No TVs. Would have liked to know that going in. Otherwise, prefect spot. ##### George Stayed 2 nights in May 2025 ### 10/10 Excellent #### Julia D. Sep 12, 2024 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!!! ##### Julia D. Stayed 3 nights in Aug 2024 ### 10/10 Excellent #### June M. Sep 7, 2024 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. ##### June M. Stayed 2 nights in Sep 2024 ### 10/10 Excellent #### JOSE F. Jul 21, 2024 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. ##### JOSE F. Stayed 4 nights in Jul 2024 ### 10/10 Excellent #### Tammy S. Apr 14, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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! ##### Tammy S. Stayed 2 nights in Mar 2025 ### 10/10 Excellent #### henny m. Jun 24, 2023 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. ##### henny m. Stayed 6 nights in Jun 2023 ### 10/10 Excellent #### Christopher B. May 5, 2024 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. ##### Christopher B. Stayed 3 nights in May 2024 ### 10/10 Excellent #### James B. Aug 25, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### James B. Stayed 2 nights in Aug 2024 ### 10/10 Excellent #### John L. Oct 16, 2023 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. ##### John L. Stayed 2 nights in Oct 2023 ### 10/10 Excellent #### Philip B. Dec 29, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Philip B. Stayed 6 nights in Dec 2023 ### 10/10 Excellent #### andrew k. Jul 25, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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! ##### andrew k. Stayed 3 nights in Jul 2024 ### 10/10 Excellent #### Sean H. Jul 6, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Peaceful A lovely place to stay right in the middle of Chestertown. Clean and welcoming. Definitely recommend. ##### Sean H. 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