Chestertown Maryland Romantic Getaways and Historic Inns
MID-ATLANTIC ROMANTIC GETAWAYS Chestertown Maryland Romantic Getaways and Historic Inns
Chestertown Maryland Romantic Getaways and Historic Inns
Chestertown, Maryland

Including Eastern Kent County.


Chestertown Maryland Tourism Guide

  • Walk along picturesque Red-Brick Sidewalks lined by 18th & 19th century homes and grand brick mansions, Inns, restaurants, antique & unique shops in Chestertown. Enjoy a Historic Chestertown Guided Tour and see the Historical Society's Geddes-Piper House Museum.
  • Attend a concert or theater production at Washington College, Prince Theatre or an evening Summer Concert on the town square.
  • Enjoy a Chester River charter or cruise or explore the river by kayak or canoe.
  • Take a Driving Tour of Kent County including Betterton, a waterfront village with a 3 acre sand beach, Georgetown, a scenic yachting center, Rock Hall, a small fishing village with three museums and Worton & the Kent Museum. Driving tour brochures available 410.778-0416.


Chestertown Maryland Accommodations

  Bed & Breakfasts and small Romantic Hotels

Great Oak Manor B&B, 10568 Cliff Rd., Chestertown. 9 guest rooms & 2 suites, most w/water views, five w/fireplaces in a c.1938 Georgian-style country mansion furnished with antiques. Location: 12 acres on the Chesapeake Bay 8 miles from town. Amenities: Screened gazebo, porches with rockers, shaded lawns and gardens & beach. Bicycles & helmets. Evening port, shery. Golf, swimming & tennis privileges. 410.778.5943 or 800.504.3098. email Rooms Air Conditioned Private Bathrooms Off Street Parking Full Breakfast incl. in Room Rate Afternoon Refreshments TV's in all Guest Rooms Not Accessible to Wheelchairs Guest Internet Access Room(s) with a Fireplace No Pets Accepted $125-$199 per night Double Occupancy $200-$299 per night Double Occupancy

www.GreatOak.com
Click Here for More Information on Great Oak Manor B&B

Inn at Mitchell House, The, 8796 Maryland Pkwy., Tolchester. 6 rooms & suites, some w/fireplaces, poster or canopy beds in a two-story Colonial manor house built in 1743 and furnished in colonial antiques and period reproductions. Cottage w/full kitchen avail. Location: 10 wooded waterfront acres near town. Amenities: Screened porch, gardens, tennis court, private beach, stream and pond. Complimentary beverages. Year-round. 410.778.6500. email Rooms Air Conditioned Private Bathrooms Off Street Parking Full Breakfast incl. in Room Rate TV's in Guest Rooms Not Accessible to Wheelchairs Guest Internet Access Room(s) with a Fireplace Under $125 per night Double Occupancy $125-$199 per night Double Occupancy $200-$299 per night Double Occupancy

www.InnAtMitchellHouse.com
Click Here for More Information on the Inn at Mitchell House

Brampton Inn Bed & Breakfast

Brampton Inn Bed & Breakfast, 25227 Chestertown Rd., Chestertown. 8 guest rooms and 2 suites most with fireplaces and some w/canopy beds and/or double whirlpool tubs in an 1860 Greek Revival plantation house and two cottages decorated in antiques and period reproductions. Location: On 35 country acres one mile south of town. Amenities: Porch, swing, landscaped gardens, pond, creek & walking paths. 410.778.1860, 866.305.1860. email Rooms Air Conditioned Private Bathrooms Off Street Parking Full Breakfast incl. in Room Rate Afternoon Refreshments TV's in Guest Rooms Wheelchair Accessible Room(s) with a Fireplace Room(s) with a private Whirlpool Pets Accepted with notice $125-$199 per night Double Occupancy $200-$299 per night Double Occupancy


Carrousel Horse Bed & Breakfast

Carrousel Horse Bed & Breakfast, 145 North Main St., Galena. 2 guest rooms, some with fireplaces in a three-story Colonial-style home built c.1880 and furnished with period antiques. Location: Situated on 3 acres one mile from the Sassafras River in a small rural village northeast of Chestertown. Amenities: Large shaded porch, landscaped lawns & gardens. 410.648.5476. Rooms Air Conditioned Private Bathrooms and Shared Bathrooms Off Street Parking Continental Breakfast incl. in Room Rate Not Accessible to Wheelchairs Room(s) with a Fireplace Under $125 per night Double Occupancy


Claddaugh Farm Bed & Breakfast

Claddaugh Farm Bed & Breakfast, 160 Claddaugh Ln., Chestertown. 4 guest rooms, some with poster or sleigh beds in a three-story Victorian farmhouse built in 1904 with antiques in a traditional style decor. Location: 8 acres, surrounded by farmlands, 2 miles from Chestertown. Amenities: Front porch with wicker and rockers, picnic area & garden. Beverages and evening sweet. Gift basket, flowers with notice. 410.778.4894. email the B&B Rooms Air Conditioned Private Bathrooms and Shared Bathrooms Off Street Parking Full Breakfast incl. in Room Rate Afternoon Refreshments No TV's in Guest Rooms Not Accessible to Wheelchairs Pets Accepted with notice Under $125 per night Double Occupancy


Great Oak Manor

Great Oak Manor B&B, 10568 Cliff Rd., Chestertown. 9 guest rooms & 2 suites, most w/water views, five w/fireplaces in a c.1938 Georgian-style country mansion furnished with antiques. Location: 12 acres on the Chesapeake Bay 8 miles from town. Amenities: Screened gazebo, porches with rockers, shaded lawns and gardens & beach. Bicycles & helmets. Evening port, shery. Golf, swimming & tennis privileges. 410.778.5943 or 800.504.3098. email Rooms Air Conditioned Private Bathrooms Off Street Parking Full Breakfast incl. in Room Rate Afternoon Refreshments TV's in all Guest Rooms Not Accessible to Wheelchairs Guest Internet Access Room(s) with a Fireplace No Pets Accepted $125-$199 per night Double Occupancy $200-$299 per night Double Occupancy


Hill's Inn Bed & Breakfast

Hill's Inn Bed & Breakfast, 114 Washington Ave., Chestertown. 4 guest rooms in a three-story American Gothic style Victorian home built c.1873 and decorated in English Victorian antiques. Location: On 1 1/3 acres in a historic residential area near the center of town. Amenities: Porches with wicker furniture and rockers, landscaped grounds with lawn furniture & garden. Evening sherry. 410.778.1926. Rooms Air Conditioned Private Bathrooms Off Street Parking Continental Breakfast incl. in Room Rate Afternoon Refreshments No TV's in Guest Rooms Not Accessible to Wheelchairs some Pets Accepted with notice Under $125 per night Double Occupancy $125-$199 per night Double Occupancy


Imperial Hotel

Imperial Hotel, The, 208 High St., Chestertown. 11 rooms & 1 suite w/kitchenette in a three-story full-service Victorian hotel built in 1903 and 1 suite in a carriage house all furnished with Victorian antiques, handcrafted pieces and reproductions. Location: Center of the downtown Historic District. Amenities: Gourmet restaurant, lounge, verandas w/tables and chairs, elevator, courtyard gallery & gardens. 410.778.5000 or 800.295.0014. email the Imperial Hotel Rooms Air Conditioned Private Bathrooms Off Street Parking Continental Breakfast incl. in Room Rate TV's in Guest Rooms Wheelchair Accessible Guest Internet Access No Pets Accepted $125-$199 per night Double Occupancy $200-$299 per night Double Occupancy


Inn at Mitchell House

Inn at Mitchell House, The, 8796 Maryland Pkwy., Tolchester. 6 rooms & suites, some w/fireplaces, poster or canopy beds in a two-story Colonial manor house built in 1743 and furnished in colonial antiques and period reproductions. Cottage w/full kitchen avail. Location: 10 wooded waterfront acres near town. Amenities: Screened porch, gardens, tennis court, private beach, stream and pond. Complimentary beverages. Year-round. 410.778.6500. email Rooms Air Conditioned Private Bathrooms Off Street Parking Full Breakfast incl. in Room Rate TV's in Guest Rooms Not Accessible to Wheelchairs Guest Internet Access Room(s) with a Fireplace Under $125 per night Double Occupancy $125-$199 per night Double Occupancy $200-$299 per night Double Occupancy


Lauretum Inn Bed & Breakfast

Lauretum Inn Bed & Breakfast, 954 High St., Chestertown. 5 guest rooms including two suites, some with fireplaces in a large three-story Queen Anne style Victorian manor built c.1881. Location: On 6 hilltop acres overlooking old Chestertown. Amenities: Open and screened porches with wicker and rockers, and wide landscaped lawns & gardens. Year-round. 800.742.3236. email the Lauretum Inn B&B Rooms Air Conditioned Private Bathrooms and Shared Bathrooms Off Street Parking Continental Breakfast incl. in Room Rate Afternoon Refreshments TV's in Guest Rooms Room(s) with a Fireplace No Pets Accepted Under $125 per night Double Occupancy $125-$199 per night Double Occupancy


White Swan Tavern

White Swan Tavern, The, 231 High St., Chestertown. 4 guest rooms and 2 suites, some with fireplaces and four poster or canopy beds in a two-story Colonial brick tavern built in 1733 and decorated with Colonial antiques and period reproductions. Location: In the center of the downtown Historic District. Amenities: Front porch, brick and flagstone courtyard with tables, exhibits & garden. Health club privileges. Beverages. Year-round. 410.778.2300. email Rooms Air Conditioned Private Bathrooms Off Street Parking Continental Breakfast incl. in Room Rate Afternoon Refreshments No TV's in Guest Rooms Wheelchair Accessible Room(s) with a Fireplace somePets Accepted with notice $125-$199 per night Double Occupancy $200-$299 per night Double Occupancy


Widow's Walk Inn Bed & Breakfast

Widow's Walk Inn Bed & Breakfast, 402 High St., Chestertown. 3 guest rooms and 2 suites in a three-story clapboard Victorian home built c.1877 and furnished eclectic-style with antiques and family heirlooms. Location: Situated on the main street in the downtown Historic District. Amenities: Large porch with rockers and swing, rear patio & gardens. Year-round. 410.778.6455 or 888.778.6455. Rooms Air Conditioned Private Bathrooms and Shared Bathrooms Continental Breakfast incl. in Room Rate No TV's in Guest Rooms Not Accessible to Wheelchairs No Pets Accepted Under $125 per night Double Occupancy $125-$199 per night Double Occupancy


  Romantic Hotels and Motels
Comfort Suites

Comfort Suites, 160 Scheeler Rd., Chestertown. 53 spacious suites with separate bedroom and sitting areas, all with microwaves and refrigerators and some with whirlpool tubs in a modern three-story motel built in 1996 and decorated in a traditional motel style. Location: In town, about 1½ miles from the Historic District. Amenities: Heated indoor pool, 24-hour comp coffee & tea available. Rooms Air Conditioned Private Bathrooms Off Street Parking Continental Breakfast incl. in Room Rate Afternoon Refreshments TV's in Guest Rooms Wheelchair Accessible Guest Internet Access Room(s) with a private Whirlpool No Pets Accepted Swimming Pool
More information and rates


Great Oak Landing Lodge

Great Oak Landing Lodge, 22170 Great Oak Landing Rd., Fairlee Creek. 28 spacious rooms, all w/remodeled bathrooms in a contemporary resort motel. Location: On 70 waterfront acres on Fairlee Creek about 8 miles to Chestertown. Amenities: Restaurant, deli/carryout, deck, poolside bar, pool, hot tub, 600 foot beach, 9 hole golf course, marina, tennis courts, bike rentals, fishing & hunting. Seasonal. 410.778.2100 or 800.LANDING. email Rooms Air Conditioned Private Bathrooms Off Street Parking No Breakfast incl. in Room Rate TV's in Guest Rooms Wheelchair Accessible Pets Accepted with notice w/fee Swimming Pool Under $125 per night Double Occupancy $125-$199 per night Double Occupancy


Have you been on a romantic getaway in Maryland or know of a romantic
hideaway not listed on this site? Please CONTACT US and let us know about it!

Please Tell Your Innkeeper The Mid-Atlantic Romantic Getaways website sent you.
www.MarylandRomanticGetaways.com

Chestertown Maryland Festivals
May - Tea Party Festival, Chestertown.
March - Arts & Crafts Show, Chestertown.
June - Chestertown Gala Garden Party, Chestertown.
July - Fireworks & Boat Parade, Georgetown.
July - Chestertown Crazy Days.
July - Kent County Fair, Tolchester.
Aug. - Betterton Beach Day, Betterton.
Oct. - Wildlife Show & Sale, Chestertown.
Oct. - Tea Time House Tour, Chestertown.
Nov. - Sultana Downrigging & Art Weekend.
Dec. - Christmas House Tour, Chestertown.
Chestertown Maryland Tourist Information

Kent County Tourism Office
email Kent County Tourism
410.778.0416.

Chestertown Information
410.810.2830.


KEY TO SYMBOLS
Rooms Air Conditioned Rooms Air Conditioned
No Air Conditioning No Air Conditioning
Private Bathrooms Private Bathrooms
Shared Bathrooms Shared Bathrooms
Off Street Parking Off Street Parking
No Off Street Parking No Off Street Parking
Full Breakfast incl. in Room Rate Full Breakfast included in rate
Continental Breakfast incl. in Room Rate Continental Breakfast incl.
No Breakfast incl. in Room Rate No Breakfast included in rate
Afternoon Refreshments Afternoon Refreshments
Television's in Guest Rooms TV's in Guest Rooms
No Television's in Guest Rooms No TV's in Guest Rooms
Guest Internet Access Guest Internet Access
Wheelchair Accessible Wheelchair Accessible
Not Accessible to Wheelchairs No Wheelchair Access
Swimming Pool Swimming Pool
Room(s) with a Fireplace Room(s) with a Fireplace
Room(s) with private Whirlpool Room(s) w/private Whirlpool
Pets Accepted with notice Accept Pets w/notice
No Pets Accepted No Pets Accepted
Less than $125/night Double Occupancy Under $125 per night
$125-$199 per night Double Occupancy $125-$199 per night
$200-$299 per night Double Occupancy $200-$299 per night
Over $299/night Double Occupancy Over $299 per night

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Chestertown Maryland Romantic Getaways and Historic Inns