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) ![Outdoor dining](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/b30cfa2a.jpg?impolicy=resizecrop&rw=297&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) ![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) ![Interior](https://images.trvl-media.com/lodging/84000000/83930000/83926700/83926700/dc0d7c61.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 106 reviews CA $138 CA $222 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-25&endDate=2025-11-26&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=2025-12-04&endDate=2025-12-05&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=2025-12-04&endDate=2025-12-05&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 $436 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24&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=2025-12-04&endDate=2025-12-05&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=2025-12-04&endDate=2025-12-05&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. Pet friendly cabin at waterfront farm! Chestertown - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 10 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-04&endDate=2025-12-05&selected=113417810&PinnedHotelID=113417810&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/102000000/101992100/101992099/w507h683x259y0-6d253ed0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest Chestertown - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 19 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-04&endDate=2025-12-05&selected=101992099&PinnedHotelID=101992099&HadPinnedHotel=true®ionId=-1&adults=2) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119130000/119124200/119124197/a6438229.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!! Chestertown - Washer - Dryer - Air conditioning 10 Exceptional 2 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-04&endDate=2025-12-05&selected=119124197&PinnedHotelID=119124197&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/63000000/62980000/62979100/62979011/fa04023d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautiful, spacious waterfront home, an easy walk to historic Chestertown Chestertown - Kitchen - Washer - Dryer - Air conditioning 9.8 Exceptional 23 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-04&endDate=2025-12-05&selected=62979011&PinnedHotelID=62979011&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 Failure to complete these may result in a negative review from the host. ### Rules 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. ### 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¢er=39.213448,-76.06999&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:cwjnFllhoM%3FS%3FS%3FS%40S%3FS%40S%40U%40S%40SBS%40Q%40SBSBSBSBSBQDSBSDQDSBQDQDSFQDQFQFQDQFQFQFOFQHOFOHQFOHOHOHOHOHMHOJMJMHMJMJMHMLMHKLKJKJKJKLIJMLILILKJGLILILILGNGLGLGLGNELELENGLENENCLCNCLCNCNCNALCNANANAN%3FNAL%3FN%3FN%3FN%3FN%40N%3FN%40L%40N%40NBL%40NBNBNBLBNBNBLDNDLFNDLDLDNFLFLFLFNHJFLHLHLFLJJHLHLLJHLJJJJJJJJJJLJLJLJLHLJLHLHNHLJNHNHNFNHNFPHNFNFPHNFPFPDPFPDPFPDPDRDPDPDRBPDRBRBPBRBRBRBRBR%40P%40R%40RBR%3FT%40R%40R%3FR%40R%3FR%3FR%3FR%3FTAR%3FRARAP%3FTCRARARARCRCRCRCPCRCRCPERCREPEREPEPEPGPEPGREPGNGPIPGNGNIPGNIPGLIPILKNILINILKNIJKLKLKLKLKJKJKJKJMJKJMJMHKJMHMHMFMHKFOHMFMFMFOFMFMDODMDODMDOBOBMDO%40ODO%40MBO%40O%40M%40O%40O%3FO%40O%3FO%3FO%3FM%3FOAO%3FOAOAOAMAOCOAOEMAOEMCOCOEMEOEMEMEOGMGMGMGOGMGMIMIMGKIMIMKMIKKMKKKKKKKMKIKMMIMKMKMIKKOKMIOIMIOIMIQIMGQIOGQIOGOGQGQGOEQGSGQEQGQEQEQCSEQESCSEQCSCSCQCSCSASASCSASASAUAQ%3FSAS%3FS%3FU%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=E1-Ju0VKj8v5pnTYCBXEnU_oLMY=) 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 ## Expedia's Latest Trends ### Hotels > [Silver Reef Casino Resort](https://www.expedia.ca/Bellingham-Hotels-Silver-Reef-Casino-Resort.h16231932.Hotel-Information) > > [Shooting Star Casino & Hotel](https://www.expedia.ca/Thief-River-Falls-Hotels-Shooting-Star-Casino-Hotel.h28874246.Hotel-Information) > > [Canad Inns Destination Center Grand Forks](https://www.expedia.ca/Grand-Forks-Hotels-Canad-Inns-Destination-Center-Grand-Forks.h1713856.Hotel-Information) > > [C'mon Inn Hotel & Suites](https://www.expedia.ca/Grand-Forks-Hotels-Cmon-Inn-Hotel-Suites.h1510580.Hotel-Information) > > [Six Flags Great Escape Lodge & Indoor Waterpark](https://www.expedia.ca/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information) > > [Riviera Resort Palm Springs](https://www.expedia.ca/Palm-Springs-Hotels-Margaritaville-Resort-Palm-Springs.h26011.Hotel-Information) > > [Hilton Grand Vacations Club Kings’ Land Waikoloa](https://www.expedia.ca/Waikoloa-Hotels-Kings-Land-By-Hilton-Grand-Vacations.h2303745.Hotel-Information) > > [The Brook at Turning Stone Resort Casino](https://www.expedia.ca/Utica-Hotels-Turning-Stone-Resort-And-Casino.h1684407.Hotel-Information) > > [Comfort Inn Shady Grove - Gaithersburg - Rockville](https://www.expedia.ca/Bethesda-Hotels-Comfort-Inn-Shady-Grove-Gaithersburg-Rockville.h22736.Hotel-Information) > > [Seneca Allegany Resort & Casino](https://www.expedia.ca/Salamanca-Hotels-Seneca-Allegany-Resort-Casino.h2238839.Hotel-Information) > > [Isla Bella Beach Resort & Spa](https://www.expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information) > > [The Westin Desert Willow Villas, Palm Desert](https://www.expedia.ca/Palm-Springs-Hotels-The-Westin-Desert-Willow-Villas.h3304313.Hotel-Information) > > [Hyatt Vacation Club at Desert Oasis](https://www.expedia.ca/Palm-Springs-Hotels-Welk-Resorts-Palm-Springs.h1140793.Hotel-Information) > > [Akwesasne Mohawk Casino Resort and Players Inn](https://www.expedia.ca/Hogansburg-Hotels-Akwesasne-Mohawk-Casino-Resort.h6009138.Hotel-Information) > > [Harrah’s Laughlin - A Caesars Rewards Destination](https://www.expedia.ca/Laughlin-Hotels-Harrahs-Laughlin-Hotel-Casino.h43310.Hotel-Information) > > [The Westin Rancho Mirage Golf Resort & Spa](https://www.expedia.ca/Palm-Springs-Hotels-The-Westin-Mission-Hills-Golf-Resort-Spa.h4124.Hotel-Information) > > [Bavarian Inn of Frankenmuth](https://www.expedia.ca/Saginaw-Hotels-Bavarian-Inn-Of-Frankenmuth.h9809515.Hotel-Information) > > [The Trail in Adams - Berkshires’ Art Hotel](https://www.expedia.ca/Adams-Hotels-Topia-Inn-An-Organic-Oasis.h12259511.Hotel-Information) > > [The Breakers Palm Beach](https://www.expedia.ca/Palm-Beach-Hotels-The-Breakers-Palm-Beach.h8479.Hotel-Information) > > [Hilton Waikoloa Village](https://www.expedia.ca/Waikoloa-Hotels-Hilton-Waikoloa-Village.h19640.Hotel-Information) > > [Angel Of The Winds Casino Resort](https://www.expedia.ca/Everett-Hotels-Angel-Of-The-Winds-Casino-Resort.h9689970.Hotel-Information) > > [Marriott's Shadow Ridge I-The Villages](https://www.expedia.ca/Palm-Springs-Hotels-Marriotts-Shadow-Ridge.h853695.Hotel-Information) > > [Semiahmoo Resort Golf & Spa, Trademark Collection by Wyndham](https://www.expedia.ca/Bellingham-Hotels-Semiahmoo-Resort-Golf-Spa.h13986.Hotel-Information) > > [Fairmont Orchid](https://www.expedia.ca/Kamuela-Hotels-Fairmont-Orchid.h25190.Hotel-Information) > > [Tulalip Resort Casino](https://www.expedia.ca/Everett-Hotels-Tulalip-Resort-Casino.h2161524.Hotel-Information) > > [JW Marriott Desert Springs Resort & Spa](https://www.expedia.ca/Palm-Springs-Hotels-JW-Marriott-Desert-Springs-Resort-Spa.h17123.Hotel-Information) > > [Great Wolf Lodge Sandusky OH](https://www.expedia.ca/Sandusky-Hotels-Great-Wolf-Lodge-Sandusky-OH.h1183594.Hotel-Information) > > [Darien Lake Lodge on the Lake](https://www.expedia.ca/Corfu-Hotels-Darien-Lake-Lodge-On-The-Lake.h13279584.Hotel-Information) > > [La Quinta Resort & Club, Curio Collection by Hilton](https://www.expedia.ca/Palm-Springs-Hotels-La-Quinta-Resort-Club.h10916.Hotel-Information) > > [Days Inn & Suites by Wyndham Cambridge](https://www.expedia.ca/Cambridge-Hotels-Days-Inn-Suites-By-Wyndham-Cambridge.h912574.Hotel-Information)