Hotels with Parking in Chestertown MD

Brampton Bed and Breakfast Inn

Bed & Breakfast in Chestertown MD

9.5

Excellent

From $330

$

Info Categories

Bed & Breakfast with Parking

EV charging stations

Boutique-style Bed & Breakfast

Luxury Bed & Breakfast

Inn at Mitchell House

Bed & Breakfast in Chestertown MD

From $166

$

Info Categories

Bed & Breakfast with Parking

Bed & Breakfast with Rooms With Fireplace

Bed & Breakfast with Free Wi-Fi

Driftwood Inn

Motel in Chestertown MD

5.8

Rated

From $69

$

Info Categories

Motel with Parking

Dog Friendly Motel

Lodging at The Imperial

Hotel in Chestertown MD

9.5

Excellent

$

Info Categories

Hotel with Parking

Family Friendly Hotel

Hotel with Free Wi-Fi

Waterfront Millington Vacation Rental with Hot Tub!

Vacation Home in Chestertown MD

$

Info Categories

Vacation Home with Parking

Vacation Home with Free Wi-Fi

Secluded Cottage in Middle of Chestertown

Apartment in Chestertown MD

$

Info Categories

Apartment with Parking

Dog Friendly Apartment

Apartment with Free Wi-Fi

Wren Retweet

Villas in Chestertown MD

$

Info Categories

Villas with Parking

Dog Friendly Villas

Villas with Free Wi-Fi

Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office

Vacation Home in Chestertown MD

9.0

Excellent

$

Info Categories

Vacation Home with Parking

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Vacation Home in Chestertown MD

$

Info Categories

Vacation Home with Parking

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

104 more hotels nearby!

Great Oak Manor 6.3 km from Chestertown

Bed & Breakfast in Great Oak Landing MD

9.3

Excellent

From $165

$

Info Categories

Bed & Breakfast with Parking

EV charging stations

Bed & Breakfast with Rooms With Fireplace

Luxury Bed & Breakfast

Cozy Eastern Shore Farmhouse Winter Getaway! 6.9 km from Chestertown

Vacation Home in Rock Hall MD

$

Info Categories

Vacation Home with Parking

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Charming Chesapeake Bay Retreat with Stunning Views! 9.2 km from Chestertown

Vacation Home in Rock Hall MD

$

Info Categories

Vacation Home with Parking

Vacation Home with Free Wi-Fi

3-Star Vacation Home

Bayside cottage steps from the harbor 9.4 km from Chestertown

Vacation Home in Rock Hall MD

5.0

Rated

$

Info Categories

Vacation Home with Parking

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

Mariner's Motel 9.4 km from Chestertown

Motel in Rock Hall MD

10

Excellent

$

Info Categories

Motel with Parking

Dog Friendly Motel

Motel with Swimming Pool

Outdoor Pool

Mariners Motel 9.5 km from Chestertown

Accommodation in Rock Hall MD

10

Excellent

From $186

$

Info Categories

Accommodation with Parking

Dog Friendly Accommodation

Accommodation with Swimming Pool

Outdoor Pool

Inn at Osprey Point 9.5 km from Chestertown

Inn in Rock Hall MD

9.3

Excellent

From $209

$

Info Categories

Inn with Parking

EV charging stations

Dog Friendly Inn

Inn with Swimming Pool

Private Pool Outdoor Pool

Inn at Haven Harbour 9.5 km from Chestertown

Resort in Rock Hall MD

8.6

Very Good

From $280

$

Info Categories

Resort with Parking

Luxury Resort

Resort for Honeymoon

Stunning 8 Bedroom Villa on the Chesapeake Bay 10.6 km from Chestertown

Villas in Rock Hall MD

$

Info Categories

Villas with Parking

Villas near Golf Courses

Villas with Swimming Pool

Blake House Historic Estate with Private Inn 11.4 km from Chestertown

Villas in Centreville MD

$

Info Categories

Villas with Parking

Dog Friendly Villas

Villas with Swimming Pool

Outdoor Pool

Captain’s Quarters - unique home on Corsica River! 11.6 km from Chestertown

Vacation Home in Centreville MD

9.4

Excellent

$

Info Categories

Vacation Home with Parking

Vacation Home near Golf Courses

Family Friendly Vacation Home