Kent County Lodging - Vacation Rentals

With over 40 bed and breakfasts, motels, hotels, and vacation rentals, Kent County has lodging options for every taste and budget.

Banning House
Contact: Gordon Fluke
109 S. Queen St.
Chestertown, MD 21620
Phone: 215-843-0864
Email: gfluke@hotmail.com
URL: www.vrbo.com/389952
Banning House is beautifully restored in the heart of historic Chestertown. A rare find to stay in a single family home, right around the corner from town and up the street from The Chester River. You can walk to everything or simply sit outside on your front porch and enjoy the neighborhood. Lovingly restored this home has updated baths and kitchen but retains the character of Chestertown with hardwood floors, architectural molding, multiple fireplaces and more. An outdoor patio is wonderful for three seasons to grill out or enjoy sunning. A perfect cottage for Washington College alumni or parents as well as for all of those interested in exploring Chestertown, Kent County and this wonderful area of the Chesapeake Bay Region.
Bay View Beach House
Contact: Barry Barr & Jim Messersmith
5783 Beach Road
Rock Hall, MD 21661
Phone: 410-639-2596
Email: tallulah@intercom.net
URL: www.tallulahsonmain.com/beach.htm
Watch sailboats by day and the lights of Baltimore by night as you enjoy the sunroom, or visit the beach located just steps from your front door. Complete with comfortable living room, a spacious kitchen, full bath, 2+ bedrooms and air conditioning. Call for reservations.
Brittland Estates
Contact: Natalie Turner
800 High Street
Chestertown, MD 21620
Phone: 410-810-7591
Email: info@BrittlandEstates.com
URL: www.brittlandestates.com/brittland.html
This secluded mansion with gardens, pool and 530 riverside acres, is old world luxury personified. The hilltop setting commands magnificent views of the Chester River. The lawns are made for grand receptions and hunting retreats. The furnished interior has many rooms and offers a grand hallway and staircase for weddings and corporate events.
Chestertown Historic House
Contact: Cathie Kempf
407 High Street
Chestertown 21620
Phone: 410-778-4526
Email: cathiekempf@comcast.net
URL: www.vrbo.com/228431
Chestertown in-town historic home, recently redone with 3 bedrooms, 4 1/2 baths (Master has 2 baths), gourmet kitchen, large family room with big screen tv, outside patio with dining area and grill, off-street parking. Walk to college, dining, farmers market, waterfront, shopping.
Chestertown Vacation Rental Ho
Contact: Kay Gatling
8013 Quaker Neck Rd
Chestertown, MD 21620
Phone: 410–708–0805
Email: Gatling@dmv.com
URL: www.homeaway.com/vacation-rental/p327358
Located less than a mile from the heart of the downtown area, this elegant home is walking distance to the Chestertown amenities which include shopping, dining, fountain park, concerts on the green, the farmers market, historic tours, garden tours, Wilmer Park, local festivals, the Sultana sailing ship and tours, marinas, charters and outdoor cafes.
Cliff Point Retreat
Contact: Holly Miller
4670 Cliffs City Road
Chestertown 21620
Phone: 717-203-7314
Email: laughingwater010@comcast.net
URL: www.cliffpointretreat.com
This simple, water-front cottage is 10 miles outside of Chestertown on the Chester River. It has 3 bedrooms, 2 baths, a wood-burning fireplace and a fully equipped kitchen. Outside there is a large deck with Adirondack chairs and a dock where the fishin' is easy.
Coveside Cottage
Contact: Liese and Jim Gillin
12060 Spring Cove Road
Rock Hall, MD 21661 21661
Phone: 410-639-2061
Email: crkayak@bluecrab.org
URL: www.springcovemanor.com/
A fully equipped home for the most discerning guests. This brand-new home-away-from home supplies every amenity one could demand. Two bedrooms, 2 full baths with skylights, a full kitchen, dining nook, living room opening onto a full deck.
Edesville Cottage
Contact: Ann Bovee
Edesveille Rd
Rock Hall 21661
Phone: 410-639-2291
Email: reservations@marinersmotel.com
URL: www.marinersmotel.com
Kayaker and family-friendly rental house near Rock Hall, minutes from seven county-maintained water access areas. House can sleep six with two bedrooms and a foldout sofa. It has two baths, full kitchen, gas grill, central AC, cable TV, ample parking. Rental includes access to swimming pool at Mariners Motel.
Evergreen Knoll Cottages
Contact: Susi Chalaire
130 1st Ave
Betterton, MD 21610
Phone: 757-572-4158
Email: evergreenknoll@yahoo.com
URL: www.evergreenknollcottages.com/
Waterfront vacation cottages on the beautiful Sassafras River with private beach and pier. Fantastic location for people who are looking for a secluded and serene vacation. Great for kayaking, canoeing, fishing and many other water activities your family can enjoy.
InnTowne House
Contact: The Inn At Huntingfield Creek
21309 Sharp St.
Rock Hall, Md 21661
Phone: 410-639-7779
Email: huntingfieldcreek@verizon.net
URL: www.huntingfield.com
Upscale, modern and new two bedroom apartment overlooking Main St. in Rock Hall. Wonderful amenities, lots of space and full kitchen. $275 per night. Up to four guests. Two night minimum, weekly rates available. Includes breakfast at Java Rock.
Kentfields Farm
Contact: Innkeeper
5793 Quaker Neck Landing Rd
Chestertown, MD 21620
Phone: 410-778-4181
Email: innkeeper@kentfieldsfarm.com
URL: www.kentfieldsfarm.com
A country estate located within 5 miles of Chestertown on the Jarrett Creek.
Langford House
Contact:
7653 Broadneck Road,
Chestertown, MD 21620
Phone: 410-708-9316
Email: rentals@langfordhouse.com
URL: www.langfordhouse.com
Spacious, comfortable pool home near Chestertown and Rock Hall. 4 bedrooms, 3 baths. Sleeps 6-8 comfortably. Spacious living/dining area, well-appointed kitchen, private office, breakfast room overlooking private in-ground pool. Satelite TV and wireless internet. Near public boat landings, marinas, restaurants. Kid and pet friendly!
Marsh Point Farm
Contact: Caulley Deringer
13787 Shallcross Wharf Road
Kennedyville, MD 21645
Phone: 703-749-9415
Email: caulley.deringer@transwestern.net
URL: NA
Vacation home for rent overlooking the Sassafras River. Property features a sandy shoreline. Home features two bedrooms, 1 full/2 half baths, and 3rd floor dorm room with views and 4 beds for kids. Fully appointed kitchen with diswasher. CAC/HWF. Weekend, week or monthly rentals available.
Peggy's Cove
Contact: Eastern Shore Vacation Rentals
29337 Glencoe Rd
Kennedyville 21645
Phone: 1-866-398-2722
Email: info@easternshorevacations.com
URL: www.easternshorevacations.com
Peggy's Cove sits on a treed parcel overlooking Sassafras River. A gorgeous tree lined view from the interior, this cottage offers a bank of windows and light in an open floor plan design. A beauitful cook's kitchen with expansive waterviews makes preparing meals a breeze. Each bedroom has its own bathroom making this cottage a great getaway for not only families but also couples and friends. A sandy beach is perfect for taking out the two kayaks included with this property.
River House on Moon Bay
Contact:
Learman Road
Chestertown, MD 21620
Phone: 866-398-2722
Email: N/A
URL: www.vrbo.com/90429
A four bedroom waterfront home outside of Chestertown with outstanding views, billards room and more. Available year round for weekly rentals.
Rock Hall Beach House
Contact: Ann Bovee/Mariners Motel
5807 Beach Road
Rock Hall, MD 21661
Phone: 410-639-2291
Email: reservations@marinersmotel.com
URL: www.marinersmotel.com
This two bedroom,1 and 1/2 bath home has large kitchen, dining area and comfortable living room. Launch your kayak from the sandy beach across the street, bike to town or enjoy the sunsets from the screened porch, the Beach House is a perfect fit for everyone on holiday.
The Overlook on Main
Contact: The Carriage House Inn
5761 Main St.
Rock Hall, Md 21661
Phone: 410-639-2855
Email: mjacob@wtrsoft.com
URL: www.carriagehousemd.com/overlook.htm
This lovely little get-away with a European flair is convenient to all the amenities of Rock Hall. Two bedroom, one bath, apartment has a master bedroom with private balcony, fully equipped kitchen, spacious living room, and a front balcony overlooking Main St.
The River House
Contact: Julia Ridgely

Rock Hall, MD 21661
Phone: 410-639-7970
Email: raelliott1@msn.com
URL:
A spacious waterfront 4 bedroom house, located 5 miles South of Rock hall. Well-furnished with spectacular views of Church Creek and Chester River. Perfect for family gatherings. Pet-friendly and very private. Kayakers welcome. Dock privledges.