Hotels with WiFi in Kent County

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.

When you stay at Inn at Huntingfield Creek in Rock Hall, you'll be on the waterfront, within a 5-minute walk of Chesapeake Bay and Northern Chesapeake Bay. This spa bed & breakfast is 1.7 mi (2.8 km) from The Mainstay and 2.2 mi (3.5 km) from Rock Hall Harbor. Pamper yourself with a visit to the spa, which offers massages. You can take advantage of recreational amenities such as an outdoor pool and bicycles to rent. Additional features at this bed & breakfast include complimentary wireless internet access, tour/ticket assistance, and a picnic area. A complimentary local cuisine breakfast is served daily from 8:30 AM to 9:00 AM. Free self parking is available onsite. Make yourself at home in one of the 12 air-conditioned rooms featuring fireplaces and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access is available to keep you connected. Private bathrooms have jetted bathtubs and complimentary toiletries.

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.

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 12.5 mi (20.1 km) from The Mainstay. This beach lodge is 16.9 mi (27.2 km) from Church Hill Theatre and 18.1 mi (29.1 km) from Eastern Neck National Wildlife Refuge. 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. Satisfy your appetite at one of the lodge's 2 restaurants. Relax with a refreshing drink at one of the 2 bars/lounges. 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.

When you stay at Haven Point Inn and Gallery in Rock Hall, you'll be near the beach, within a 10-minute walk of Chesapeake Bay and Waterman’s Museum. This hotel is 0.4 mi (0.6 km) from Ferry Park 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 9.4 mi (15.1 km) from Chesapeake Bay and 0.6 mi (1 km) from Rolling Road 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.

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.

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..

This home was originally built in 1830 and has been completely restored lovingly by its owners, and sits upon an overlook of the river. You'll feel like you've stepped back in time but still get to enjoy all of the modern conveniences. Nature is all around you in this waterfront home. Birdwatchers especially love watching the Eagles, Osprey, ducks and other waterfowl. We see deer frolicking on the embankments and the sunsets are spectacular! The property includes the use of an additional efficiency unit above the garage. (We lovingly call it "Fonzies Apartment" if you grew up in the era of "Happy Days." The kids love it, and adults do too. It's cozy and comfortable and a nice space to get away from the main the house. The property can sleep up to 12 guests overnight. The property includes a screened-in porch facing the waterfront view, a fire pit, kayaks and paddleboards, and fishing from the dock. (Bring your own poles and bait.) You can explore the shoreline or take a nap in the window seat overlooking the water. Some folks even enjoy a swim on the creek side of the house. Our guests tell us that the screened-in porch is their favorite part of their stay. It's serene. Morning coffees, and family time together over lunch or dinner and just sitting there together talking are really special. Secluded and out-of-the-way, yet 15 minutes from major shopping. There are multiple nearby marinas and great restaurants like Deep Blue at the Kitty Knight House and The Granary, both are just a 2 minute drive. A mile away, the friendly folks at Twinney's serve up home style favorites. For night life and other fun, go to Chesapeake City (We like The Chesapeake Inn, Schaefers Canal House and Prime.) You can also head to Chestertown for another vibe and great options. Annapolis is only an hour away if you are feeling adventurous! If you like to get your steps in, a walk up the drive to the main road is relaxing. Within 5 minutes, you'll find great produce, baked goods and everything you need at Cross Street Market, there is also a convenience store with liquor, packaged goods and sandwiches. In Middletown, you'll find everything you need including Dutch Country Farmers Market open Thursdays, Fridays and Saturdays. We offer a wide selection of board games for the homebodies who want to bond around the table with some competitive fun and family memories! About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Waterfront and dock areas are "use at your own risk". You must wear life jackets when using the SUPs or kayaks. Guest watercraft are not permitted..Please close all doors/windows when running the A/C, or the heat.,No parking on the grass at any time..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:Events allowed: family gatherings and birthday parties.Maximum event attendees: 18,Small family gatherings are fine..

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.