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 lies at the banks of Chester River and the town is blessed with several interesting destinations. It is because of these that this once sleepy town has been transformed into one of Maryland's best vacation areas. Chestertown bed and breakfast inns have taken advantage of this situation. In the evenings, spend hours of entertainment at Prince Theatre, where live performances are frequently held for public viewing. Walk along the waterfront promenade, a well-kept scenic attraction in Chestertown which features views of the schooner Sultana. Other beautiful boats that are often in town are the Skipjack and Buyboat, both owned and maintained by Echo Hill Outdoor School. Spend a lazy afternoon just sitting at the Fountain Park or shop at the nearby Artisans' Market and Farmers' Market. Remember to stay at a Chestertown bed and breakfast and you will be delighted with your entire getaway. By Great Oak Manor.

10 bed and breakfast inns found.

1. 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...

2. 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...

3. 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...

4. 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

5. 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...

Bed and breakfast inns near Chestertown, Maryland

Inn at Osprey Point

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...

Inn at Huntingfield Creek

Experience Chesapeake tradition at this four-season refuge on 70 acres of natural beauty. The telescope farmhouse features an eclectic blend of Country French,...

Moonlight Bay Inn

Moonlight 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...

Spencer Silver Mansion

This elegant granite Victorian mansion is graced with bays, gables, balconies, a turret and a gazebo veranda. The Victorian decor, with antiques and Oriental...

Annapolitan

Relax on the wicker furnishings that grace the veranda, a wraparound porch. Catch a top name music act at Rams Head Tavern and enjoy one of the numerous...

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