Kent County Hotels with Wifi

When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland. This hotel is 1.6 mi (2.6 km) from River Arts Chestertown and 5.9 mi (9.6 km) from Rolphs Wharf Marina. Be sure to enjoy recreational amenities including a fitness center and a seasonal outdoor pool. Additional amenities at this hotel include complimentary wireless internet access, a fireplace in the lobby, and a banquet hall. A complimentary full breakfast is served on weekdays from 6:30 AM to 9:30 AM. Featured amenities include a business center, a 24-hour front desk, and laundry facilities. Free self parking is available onsite. Make yourself at home in one of the 81 guestrooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature designer toiletries and hair dryers. Conveniences include desks and microwaves, as well as phones with free local calls.

Red Roof Inn & Suites Chestertown, Maryland is a pet-friendly, family-friendly discount hotel. This hotel is close to Washington College, Chestertown Marina, Wilmer Park, Chesapeake Farms Wildlife Habitat Tour as well as numerous historical sites and museums such as Chestertown Electric , Historical Society-Kent County, Sumner Hall, Kent County Museum, Rock Hall Marine Restoration & Heritage Center, and the Waterman’s Museum. Red Roof Inn & Suites Chestertown features interior corridors, and a guest coin laundry. All rooms at this Red Roof Inn & Suites offer free Wi-Fi, a flat screen TV, microwave, mini-fridge, in-room coffee maker, hair dryer, iron & ironing board, desk, free in-room safe and a free expanded cable package featuring HBO. Experience our coffeehouse-style coffee and tea. One well-behaved family pet per room is welcome at Red Roof Inn & Suites Chestertown.

When you stay at Haven Point Inn and Gallery in Rock Hall, you'll be near the beach, within a 10-minute walk of Waterman’s Museum and Ferry Park. This hotel is 0.4 mi (0.7 km) from Chesapeake Bay and 0.4 mi (0.7 km) from Northern Chesapeake Bay. Relax with a refreshing drink at one of the 5 beach bars. A complimentary cooked-to-order breakfast is served on weekends from 8:30 AM to 9:30 AM. Free self parking is available onsite. Make yourself at home in one of the 4 guestrooms featuring refrigerators. Rooms have private balconies. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Bathrooms have showers and hair dryers.

With a stay at Driftwood Inn in Chestertown, you'll be a 3-minute walk from Washington College and 11 minutes by foot from Larrabee Arts Center. This motel is 0.6 mi (1 km) from Rolling Road Park and 0.7 mi (1.1 km) from Chestertown Dog Park. This motel has 1 floor in 2 buildings and offers designated smoking areas. Featured amenities include express check-in, express check-out, and a 24-hour front desk. Free self parking is available onsite. Make yourself at home in one of the 28 guestrooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.

With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater. This beach lodge is 12.5 mi (20.1 km) from The Mainstay and 16.9 mi (27.2 km) from Church Hill Theatre. Practice your swing on the golf course or soak up the sunshine on the private beach. This lodge also features complimentary wireless internet access, gift shops/newsstands, and a picnic area. Featured amenities include laundry facilities, ATM/banking services, and coffee/tea in a common area. Free self parking is available onsite. Stay in one of 26 guestrooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, and housekeeping is provided on request.

Our lovingly-restored Millington Manor is the original home of the local doctor, built in 1868. Our small town has a liquor store and grocery.We are a 15-minute ride to Chestertown, home of Washington College and host to wonderful restaurants, lovely shops, galleries and more!The spaceYour suite will be clean and ready for your arrival with everything you need for a comfortable stay. WIFI is included and information on the area will be in your room. Fresh ice, water, coffee, tea and snacks will also be provided. You will also have access to a lounge, which is a comfortable place to read a book, have a conversation or watch TV.Guest accessYou have your bedroom and bathroom to yourself. The lounge is shared. Please note, the bedroom suite is on the second floor. Access is by stairs.During your staySomeone will be available in person or by phone or text to answer any questions you have about the house or area. Your separate entrance opens digitally and is changed with each new occupant, so you will be able to come and go independently.We include a few snacks, water and self-service breakfast items plus coffee, tea, etc. Unlike a B and B, this is self-service and you may even use the microwave to heat things. There is also a small refrigerator in the suite. If you need something that is not provided in the list, please ask. We will do whatever we can, within reason, to accommodate.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

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- PatioAdditionally, 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!" - CarlaWe'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!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.While not child friendly, we can accommodate..About customRules: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..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped with a queen sized bed, linens, washer/dryer, microwave, refrigerator, dinette, toiletries, lux robes... everything you could possibly need to escape the hustle and bustle of life. An additional sleeper sofa, crib, etc. are available at request. Walk to the waterfront or historic district, ride bikes on back country roads. We are more than happy to help arrange paddleboard and kayak adventures! *We require guests to have a verified profile by VRBO OR verification by ID prior to stay*About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:There is a 0 smoking tolerance policy. Any evidence of inside smoking will result in a $250 fee..Pets may not be left alone. No pets in the pool.,Any evidence of illicit drug use will result in a $500 fee, immediate eviction without refund and notification of law enforcement..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.

Chester River Dreams, offers spectacular views of the Chester River from the Family room, 2 bedrooms, Kitchen, & Dining room, Deck, not to mention from the 'L' head on the dock. All the other rooms enjoy a view of a large pond where you can watch Osprey, Eagles & Heron enjoy the fishing site. Most evenings you can listen to the Bull frogs sing. There are 3 large bedrooms (3 queen beds + 2 twins.) Each bedroom has smart TVs. Two have views of the river & the other has views of the large pond out front. The family room features a queen sleeper sofa with air mattress & has a view of the river. The family room features hardwood flooring, wet bar w/wine frig, recessed lighting, smart TV, and decorative fireplace. The kitchen & dining area feature an open floor plan with ceramic tile flooring, cherry cabinetry, granite counter tops, & a raised bar between the kitchen & dining area. There are double pocket doors into the family room for privacy. There are sliding glass doors from the dining area that will go out to a large deck that has a cushion patio set & umbrella. There is a laundry area that includes a stacked washer & dryer. All bathrooms have been renovated. There is a full living room with a view of a large pond. Plenty of parking, a small beach, 50' dock w/10X20 'L' head to relax & watch the sunrise or fish/crab. Bar-B-Que grill, (propane) as well as plenty of Adirondack chairs. Kayaks & paddle boat & boards are available (pls note, although there are 4 adults life vests, we do not supply children's life vests. Although, we have young grandchildren & as long as they are not in use, feel free to borrow.) There is also a fire pit for those cool nights or to just hang out and make smoors. High speed internet added in 2021 NEW for 2022! The interior and exterior have been freshly painted. New siding and new living room furniture, new patio cushions, 6 smart tv's & ceiling fans. New for 2025! upstairs bedroom with walk in closet and private bath. HUNTERS WELCOME!! For any of you NASCAR fans, we are situated only 40 minutes from Dover Track. We are also 25 minutes from Rock Hall & 45 minutes from Annapolis. 35 minutes from premium outlets in Queenstown.** Some dates to consider for fun filled family weeks.Chestertown Tea Party is every memorial day weekend, Rock fish tournaments usually early June and mid Sept Sunday on 4th of July weekends is Waterman's day in Rock Hall, 7/3 Fireworks in Rock Hall, 7/4 Fireworks in Chestertown and parade in Rock Hall. All times are great with lots to do but, if you have never been to this part of the eastern shore then these are the best times. This whole area is loaded with festivals. Here's a few more.Bettertown days @ Betterton Beach usually the fist weekend in Aug The second weekend in Aug is pirate's weekend in Rock Hall another great time to be had. Lots of people dress up for the event. In Chestertown, Sultana down rigging late Oct early Nov, early Dec is Dicken's weekend & early Oct is Rock Hall's Fallfest. Every Sat. till noon in Chestertown's Fountain park, is the farmer's market. Lots of times on Fridays or Saturday evenings(in season) they have entertainment in Fountain park. On the first Friday of every month is 1st Friday in Chestertown(all year long). Many stores stay open and have snacks (wine & beer too) and some have entertainment all FREE. Lots of people walking around during these events. A great way to get to know the town. 3rd Thurs 6-8 pm is cars on high April thru Oct.Wilmer park has events as well. There are concerts, taste of the town to name a few. If you are planning a certain week and would like to know the events near town, just ask and I will do my best to list everything I know. Feel free to surf the web as well. Most of the local towns have event calendars you can find online.Special winter monthly rentals available (rate does not include utilities for stays exceeding 30 days.) Please be aware, that there are no fences. Neighbor has two dogs that are very friendly and may come over to greet you.FYI, the school zone has camera 24/7, so watch your speed.About pets:Pets allowed: less than 50 lbs per pet (limit 2 pets total).4 pets weighting over 60lbs, please contact owner..About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Beach towels are not provided. Do not use bath towels for beach or pets. No wet pets in the house, No pets on the furniture. Do not use bedding 4 pets.Smoking is permitted outside the house. Take care not to let smoke inside. Extra fees may be charged if cigarette/cigar odors are inside the house.,Minimum of 2 night are required EXCEPT for holidays. Minimum of 3 nights for ALL holidays. NO SATURDAY check- in for 7 days or longer..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Easy walk to everything in Rock Hall - The beach, the marinas, restaurants, bars and shops. 15 minute drive to historic Chestertown. Large rooms with plenty of common space to relax. First floor wheelchair accessible suite. Two zone central AC. New kitchen, baths, beds, floors and paint 2022. Sit on the front porch and watch all the other happy people walk and pedal by.Here's a review from a guest with a handicapped child: "Great property. Very clean. My daughter is in a wheelchair and I have rented houses that state they are wheelchair accessible in the past only to find they actually are not. This house was 100% wheelchair accessible. My daughter had a great time and was able to easily move around the first floor. The hosts are great as well. Very good with communication and very gracious. Would stay again!Date of arrival - June 20, 2025"About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 20,Contact us for details about event planning..