Chestertown Bed and Breakfast Inns
Chestertown bed and breakfast travel guide for romantic, historic and adventure b&b's. Browse through the iLoveInns.com database of Chestertown, Maryland bed and breakfasts and country inns to find detailed listings that include room rates, special deals and area activities. You can click on the 'check rates and availability' button to contact the innkeeper.
Chestertown has become a perfect vacation destination. The people are warm and friendly, the atmosphere is very relaxing, and there are amazing Chestertown bed and breakfast inns. Go shopping at Fountain Park and take the time to shop at Farmers' Market or at Artisans' Market. The waterfront area of Chestertown is also a favorite destination. Check out the Schooner Sultana, which is an educational sailing ship built in the town. Buyboat and Skipjack owned by Echo Hill Outdoor School is also found there. In the evenings, watch live performances at Prince Theatre. There may also be a Concert at the Park. An interesting time to visit Chestertown is when it is also celebrating Tea Part or the Wild Owl Festival. By White Swan Tavern.
Chestertown has become a perfect vacation destination. The people are warm and friendly, the atmosphere is very relaxing, and there are amazing Chestertown bed and breakfast inns. Go shopping at Fountain Park and take the time to shop at Farmers' Market or at Artisans' Market. The waterfront area of Chestertown is also a favorite destination. Check out the Schooner Sultana, which is an educational sailing ship built in the town. Buyboat and Skipjack owned by Echo Hill Outdoor School is also found there. In the evenings, watch live performances at Prince Theatre. There may also be a Concert at the Park. An interesting time to visit Chestertown is when it is also celebrating Tea Part or the Wild Owl Festival. By White Swan Tavern.
![]() | |
|
9 bed and breakfast inns found.
FEATURED INNS Innkeepers, feature your inn here for free!
1. Great Oak Manor - Chestertown, MD
This elegant Georgian mansion anchors vast lawns at the end of a long driveway. Situated directly on the Chesapeake Bay, it is a serene and picturesque country...
2. The Inn at Mitchell House - Chestertown, MD
This pristine 18th-century manor house sits as a jewel on 12 acres overlooking Stoneybrook Pond. The guest rooms and the inn's several parlors are preserved...
3. Simply Bed & Bread - Chestertown, MD
What we hope we're doing here is simply serving up a slice of home.
"Staying here is like going back in time to your childhood, or to the childhood you wish you'd had." -- Jan, a recent guest
![]() 4. Brampton Inn - Chestertown, MD
Swiss innkeeper Danielle Hanscom selected family antiques to furnish the parlor and dining room. A massive walnut staircase winds to the upstairs where...
5. White Swan Tavern - Chestertown, MD
During the 1978 restoration of this inn, an archeological dig made an interesting discovery. His one-room dwelling is now a converted guest room. After...
![]() Bed and breakfast inns near Chestertown, MarylandMoonlight Bay offers an ideal setting, right at the edge of the Chesapeake Bay. The pre-Civil War home includes a veranda lined with wicker furnishings and a...
![]() Experience Chesapeake tradition at this four-season refuge on 70 acres of natural beauty. The telescope farmhouse features an eclectic blend of Country French,...
![]() Spread over 30 acres on the Eastern Shore, this inn and restaurant are open year-round with a marina accessible during boat season. A casual and friendly...
This elegant granite Victorian mansion is graced with bays, gables, balconies, a turret and a gazebo veranda. The Victorian decor, with antiques and Oriental...
![]() Find more Chestertown Bed and Breakfasts ![]() |
QUICK SEARCH
![]() Nearby Cities
|





























