Vacation Rentals in Kent County

Banning House
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 a beautifully restored single family home in the heart of historic Chestertown up the street from The Chester River. You can walk to everything or simply sit outside on your front porch and enjoy the neighborhood. An outdoor patio is wonderful for three seasons to grill out or enjoy sunning.

Bay Cottage
Bay Cottage
Contact: Ann Bovee
S. Hawthorne
Rock Hall, MD 21661
Phone: 410-639-2291
Email: reservations@marinersmotel.com
URL: www.marinersmotel.com
Located in Rock Hall one block from Rock Hall Harbor, offers 2 bedrooms, 1 bath and a pull out queen sized sofa. A fully equipped kitchen and gas grill with outdoor seating. Small pets are welcome on this fenced property. Cable TV and a secure wireless connection are available.

Bay View Beach House
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.

Bayside Retreat
Bayside Retreat
Contact: Ann Bovee
21017 Bayside Ave
Rock Hall, MD 21661
Phone: 410-639-2291
Email: reservations@marinersmotel.com
URL: www.marinersmotel.com
Bayside Retreat has 3 bedrooms and 1 1/2 baths and is located a short walk away from great restaurants on the harbor. Guests also enjoy pool privileges at Rock Hall Landing Marina just 50 yards away.

The Beach Cottage
The Beach Cottage
Contact: Diane Oliver
5791 Beach Road
Rock Hall, MD 21661
Phone: 410-708-5589
Email: dianeoliver98@gmail.com
URL: www.rockhallrentals.com
Beach Front Cottage Get-A-Way Newly renovated, charming cottage with a sandy beach right across the quiet street. Beach is great for swimming, kayaking or just gazing at the boats passing by in the distance. Amazing sunsets in the quaint town of Rock Hall await you. Cottage has 2 bedrooms, 1 bath, sleeps 5, central air, outdoor shower, and kitchen. Great family getaway.

Brittland Estates
Brittland Estates
Contact: Natalie Turner
211 Brittland Farm Lane
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.

Chez Bonheur
Chez Bonheur
Contact: Angela Eade

Chestertown, MD 21620
Phone: 443-786-7220
Email: inquiries@tidewatervacations.com
URL: www.tidewatervacations.com/chexbonheur/
Magnificent 1000 acre estate just 5 miles outside Chestertown. Contemporary style 6 br home sited perfectly high above the river, ideal for fishing and kayaking, wonderful views of the sun setting over the water. House has fully equipped kitchen, pool, dock and dock house, Wi-Fi, W/D, AC, BBQ, linens provided.

Cliff Point Retreat
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.

Coleman Cottage
Coleman Cottage
Contact: Cindy Genther
5882 Coleman Road
Rock Hall, MD 21661
Phone: 410-639-4003
Email: cindy@rockhallproperties.com
URL: www.youtube.com/watch?v=fBjk2GtKvNo&feature=plcp
Coleman Cottage vacation rental was recently renovated and includes all new bedding, furniture, appliances and bath. There are two bedrooms, one bath, plus living room with sleeper sofa and fully-equipped kitchen. Heat and AC.

Coveside Cottage
Coveside Cottage
Contact: Liese and Jim Gillin
12060 Spring Cove Road
Rock Hall, MD  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
Edesville Cottage
Contact: Ann Bovee
Edesville Rd
Rock Hall, MD 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
Evergreen Knoll Cottages
Contact: Susi Chalaire
130 1st Ave
Betterton, MD 21610
Phone: 410-348-5051
Email: evergreenknoll@yahoo.com
URL: www.evergreenknollcottages.blogspot.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.

Harbor View Condo
Harbor View Condo
Contact: Diane Oliver
21090 Sharp Street #132
Rock Hall, MD 21661
Phone: 410-708-5589
Email: dianeoliver98@gmail.com
URL: www.rockhallrentals.com
Enjoy all the amenities of home in this 2BR, 2 BA condo with deck overlooking Rock Hall's Harbor and boat activity. Close to restaurants, shopping and waterfront activities.Walk or bike to local beach, or wildlife refuge. Rent a kayak or take a sunset sail. An ideal getaway location in the waterfront town of Rock Hall. Sit on your deck and watch the waterfront activities before enjoying waterfront dining and entertainment.

Heron Pond Cottage
Heron Pond Cottage
Contact: Jennifer Lieber
7820 Quaker Neck Road
Chestertown, MD 21620
Phone: 410-310-8273
Email: Jennifer@pineygrovecellars.com
URL: www.vrbo.com/660425
This comfortable quiet cottage is just a mile outside of historic Chestertown. It has two bedrooms and one bath and comes complete with linens and a fully equipped kitchen. Outside there is a patio overlooking the pond with a gas grill and picnic table. Access to the Chester River is ample with a dock and sandy beach area. Kayaks and bikes are available for your enjoyment. Other amenities include high speed internet and cable. Sleeps seven and well behaved pets are always welcome! Please email or call for reservations.

InnTowne House
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
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.

The Lodge on Main
The Lodge on Main
Contact: Rick Kessinger
5718 Main Street
Rock Hall, MD 21661
Phone: 310-370-1281
Email: RockHallVacationRentals@gmail.com
URL: RockHallVacationRentals.com
Everything is crisp, clean and recently renovated. It sleeps up to 9 in three bedrooms and offers 2 full baths. The completely efficient kitchen offers an overlook on Main Street. Outside there is a very nice gazebo, side yard with BBQ grill, and off-street parking. You’ll love being on Main Street for the Rock Hall festivals, close to all the hunting and sailing and fishing spots, or just come enjoy the eastern shore charm!

Lovely Cove Farm
Lovely Cove Farm
Contact: Contact: Eastern Shore Vacatio
232542 Lovely Lane
Chestertown 21620
Phone: 410-770-9093
Email: info@easternshorevacations.com
URL: easternshorevacations.com/vacation-rental-home.asp?PageDataID=91849
A screened porch which is steps from the dock that hosts two kayaks for guests use and a simple floating dock for entry/exit. 2 single kayaks provided and note that East Langford Creek, which lies beyond the duck blind offers some of the best paddling coves and creeks on the Shore.

Marsh Point Farm
Marsh Point Farm
Contact: Caulley Deringer
13787 Shallcross Wharf Road
Kennedyville, MD 21645
Phone: 703-749-9415
Email: caulley.deringer@transwestern.net
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.

The Overlook on Main
The Overlook on Main
Contact: The Carriage House Inn
5761 Main St.
Rock Hall, MD 21661
Phone: 410-639-2855
Email: mylita@muskratalley.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.

River Lodge
River Lodge
Contact: Natalie Turner
219 Brittland Farm Lane
Chestertown, MD 21620
Phone: 410-810-7591
Email: info@BrittlandEstates.com
URL: www.brittlandestates.com/lodge.html
With its rustic, peaceful waterfront setting, the River Lodge is an excellent venue for a business retreat, private getaway, family reunion, or informal wedding; a four season destination. The Lodge is perched on the banks of the Chester River and includes a dock, front and back porches, a great room, sleeping for 9-11 people, and kitchen facilities.

Rock Hall Beach House
Rock Hall Beach House
Contact: Ann Bovee
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.

Running Fox
Running Fox
Contact: Natalie Turner
23791 Ricauds Branch Road
Chestertown, MD 21620
Phone: 410-810-7591
Email: info@BrittlandEstates.com
URL: www.brittlandestates.com/runningFox.html
This countryside property with wildlife pond and woodside fields, includes a two-story historic house and barn. Kitchen is fully equipped and modernized with adjacent dining. Upstairs houses 3 bedrooms and an interesting back wing bedroom perfect for children. Ideal for romantic get-a-ways, retreats, hunting parties or a country wedding.

Sharp Street Retreat
Sharp Street Retreat
Contact: Rick Kessinger
5718 Main Street
Rock Hall, MD 21661
Phone: 310-370-1281
Email: RockHallVacationRentals@gmail.com
URL: RockHallVacationRentals.com
This charming home on Sharp Street in Rock Hall is a perfect place to stay for you and your family and friends. This recently renovated house sleeps 10 comfortably and is just steps away from all that Rock Hall has to offer - in town and on the waterfront.

Stepne Manor
Stepne Manor
Contact: Natalie Turner
406 South Cross Street
Chestertown, MD 21620
Phone: 410-810-7591
Email: info@BrittlandEstates.com
URL: www.brittlandestates.com/stepne.html
This historic circa 1690 manor house with wide covered porch is within walking distance to downtown Chestertown. An ideal location for small retreats, meetings and town charm weddings.

Summer House
Summer House
Contact: Ann Bovee
5797 S. Hawthorne
Rock Hall, MD 21661
Phone: 410-639-2291
Email: reservations@marinersmotel.com
URL: www.marinersmotel.com
Located on one of the prettiest streets in Rock Hall, this 3 bedroom 1 bath house is within walking distance to restaurants and Rock Hall Harbor. A second floor loft bedroom and spacious backyard is perfect for the kids.The cable TV/generous living room and screened front porch make this house perfect for the whole family!

Swan Creek Waterfront w/ po
Swan Creek Waterfront w/ po
Contact: Diane Oliver
20997 Haven Road
Rock Hall, MD 21661
Phone: 410-708-5589
Email: dianeoliver98@gmail.com
URL: www.rockhallrentals.com
Swan Creek Waterfront Cottage with large yard leading to 200'+ pier for boats, crabbing, and fishing. Explore the quaint town of Rock Hall with nearby restaurants, shopping and loads of outdoor activities. Great Vacation home for family or friends. Has 3 bedrooms with 2 kings, and one with Queen and bunk beds, 1 bath, and full kitchen. Above ground pool for relaxing on large deck.

The Vineyard at Thornton
The Vineyard at Thornton
Contact: Angela Eade

Chestertown, MD 21620
Phone: 443-786-7220
Email: inquiries@tidewatervacations.com
URL: www.tidewatervacations.com/thornton/
This 350 acre farm offers accommodations for 10 in the 5 br Georgian Manor. Located on Morgnec Creek, ideal for fishing and kayaking, just minutes from fine dining restaurants, a golf course, eclectic shops, and a great farmers market. Pet friendly, Pool, Elevator, Wi-Fi, W/D, AC, BBQ, linens provided.

Welcome Aboard
Welcome Aboard
Contact: Jack Butler
5813 Clam Cove
Rock Hall, MD 21661
Phone: 610-246-9387
Email: rockhallrental@gmail.com
Welcome Aboard is a 3 bedroom and 2 1/2 bath home in Rock Hall's Harbor Woods Community. A short walk to Main Street attractions and waterfront dining. Includes Wi-fi, linens, fully equipped kitchen, BBQ, and laundry. Fireplace in living room. Sleeps 6-9 comfortably.