Lodging in Near Chestertown

Brittland Estates in Chestertown, MD
Brittland Estates
211 Brittland Farm Lane
Chestertown, MD  21620
Contact: Natalie Turner
Phone: 410-810-7591
Email: info@BrittlandEstates.com
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 in Chestertown, MD
Chez Bonheur

Chestertown, MD  21620
Contact: Angela Eade
Phone: 443-786-7220
Email: inquiries@tidewatervacations.com
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 in Chestertown
Cliff Point Retreat
4670 Cliffs City Road
Chestertown  21620
Contact: Holly Miller
Phone: 717-203-7314
Email: laughingwater010@comcast.net
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.

Crow Farm Stay B & B in Kennedyville, MD
Crow Farm Stay B & B
12441 Vansants Corner Road
Kennedyville, MD  21645
Contact: Judy Crow
Phone: 410-648-5687
Email: crowfarmmd@gmail.com
Enjoy a unique farm experience. Walk the trails on our 365 acre farm, enjoy views of the vineyard and forever fields. We're located about an hour from Baltimore, Washington, Philadelphia, Wilmington and minutes from historic Chestertown on Maryland's Eastern Shore. Wine Tasting Room open weekends 12-6pm.

Evergreen Knoll Cottages in Betterton, MD
Evergreen Knoll Cottages
130 1st Ave
Betterton, MD  21610
Contact: Susi Chalaire
Phone: 410-348-5051
Email: evergreenknoll@yahoo.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 in the Chesapeake Bay area. Great for kayaking, canoeing, fishing and many other water activities your family can enjoy.

Great Oak Manor in Chestertown, MD
Great Oak Manor
10568 Cliff Road
Chestertown, MD  21620
Contact: Scott and Kaylin Benfield
Phone: 410-778-5943
Email: info@greatoakmd.com
Elegant 12 room waterfront manor house with enchanting sunsets over the Chesapeake Bay on Maryland's Eastern Shore. With 12 acres on the waterfront, our setting serves as a destination event and wedding location. Private beach access, hammocks, Adirondack chairs, kayaks and bikes available. Located 8.5 miles from Chestertown and an hour from Baltimore, Washington D.C., and Philadelphia.

Inn at Mitchell House in Chestertown, MD
Inn at Mitchell House
8796 Maryland Parkway
Chestertown, MD  21620
Contact: Jim and Tracy Stone
Phone: 410-778-6500
Email: innkeeper@innatmitchellhouse.com
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.

Kentfields Farm in Chestertown, MD
Kentfields Farm
5793 Quaker Neck Landing Rd
Chestertown, MD  21620
Contact: Innkeeper
Phone: 410-778-4181
Email: innkeeper@kentfieldsfarm.com
A country estate located within 5 miles of Chestertown on the Jarrett Creek.

Kitty Knight House in Georgetown, MD
Kitty Knight House
14028 Augustine Herman Highway
Georgetown, MD  21930
Contact: Sandy
Phone: 410-648-5200
Email: restaurant@kittyknight.com
18th Century Charm in the 21st Century. The Kitty Knight House & Deck feature traditional Eastern Shore cuisine with a historical touch. The Kitty Knight Inn features eleven beautifully appointed rooms.

Lovely Cove Farm in Chestertown
Lovely Cove Farm
232542 Lovely Lane
Chestertown  21620
Contact: Contact: Eastern Shore Vacatio
Phone: 410-770-9093
Email: info@easternshorevacations.com
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 in Kennedyville, MD
Marsh Point Farm
13787 Shallcross Wharf Road
Kennedyville, MD  21645
Contact: Caulley Deringer
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.

Mears Great Oak Landing in Chestertown, MD
Mears Great Oak Landing
22170 Great Oak Landing Road
Chestertown, MD  21620
Contact: Mary McAllister
Phone: 410-778-5007
Email: info@mearsgreastoaklanding.com
28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.

River Inn at Rolph's Wharf in Chestertown, MD
River Inn at Rolph's Wharf
1008 Rolph's Wharf Rd
Chestertown, MD  21620
Contact: Innkeeper
Phone: 800-894-6347
Email: rolphs@aol.com
Victorian Farmhouse on the shores of the Chester River. Approximately 3 miles from Chestertown.

River Lodge in Chestertown, MD
River Lodge
219 Brittland Farm Lane
Chestertown, MD  21620
Contact: Natalie Turner
Phone: 410-810-7591
Email: info@BrittlandEstates.com
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.

Running Fox in Chestertown, MD
Running Fox
23791 Ricauds Branch Road
Chestertown, MD  21620
Contact: Natalie Turner
Phone: 410-810-7591
Email: info@BrittlandEstates.com
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.

Thornton Estate in Chestertown, MD
Thornton Estate

Chestertown, MD  21620
Contact: Lisa Hoon
Phone: 410-708-6272
Email: lhoon13@gmail.com
This 350 acre farm offers accommodations for 11 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.