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.
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.
Crow Farm
Contact: Judy Crow
12441 Vansants Corner Road
Kennedyville, MD 21645
Phone: 410-648-5687
Email: crowfarmmd@gmail.com
URL: www.crowfarmmd.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.
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.
Great Oak Manor
Contact: Cassandra Fedas
10568 Cliff Road
Chestertown, MD 21620
Phone: 410-778-5943
Email: cassandra@greatoak.com
URL: www.greatoak.com
Elegant Waterfront Manor House with spectacular Chesapeake Bay sunsets off a private beach. Located approximately 10 miles from Chestertown.
Inn at Mitchell House
Contact: Jim and Tracy Stone
8796 Maryland Parkway
Chestertown, MD 21620
Phone: 410-778-6500
Email: innkeeper@innatmitchellhouse.com
URL: www.innatmitchellhouse.com
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
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.
Mears Great Oak Landing
Contact: Manager
22170 Great Oak Landing Road
Chestertown, MD 21620
Phone: 410-778-5007
Email: info@mearsgreastoaklanding.com
URL: www.mearsgreatoaklanding.com
28 Modern Rooms, Casual Fine Dining, Swimming Pool and Golf Course. Located approximately 10 miles from Chestertown.
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.
River Inn at Rolph's Wharf
Contact: Innkeeper
1008 Rolph's Wharf Rd
Chestertown, MD 21620
Phone: 800-894-6347
Email: n/a
URL: www.rolphswharf.com
Victorian Farmhouse on the shores of the Chester River. Approximately 3 miles from Chestertown.
River Lodge
Contact: Natalie Turner
800 High Street
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.
Running Fox
Contact: Natalie Turner
800 High Street
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.
Chestertown | 118N Cross Street | Chestertown, MD 21620 | 410-778-0500 | office@chestertown.com

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