Hotels, Vacation Homes, B&Bs, Apartments in Chestertown MD

Brampton Bed and Breakfast Inn

Bed & Breakfast in Chestertown MD

9.5

Excellent

From $250

$

Info Categories

Bed & Breakfast with Parking

EV charging stations

Boutique-style Bed & Breakfast

Luxury Bed & Breakfast

Comfort Inn & Suites Chestertown

Hotel in Chestertown MD

7.6

Good

$

Info Categories

Hotel for Honeymoon

Dog Friendly Hotel

Business Hotel

Quality Suites

Hotel in Chestertown MD

$

Info Categories

Hotel with Swimming Pool

Hotel with Free Wi-Fi

3-Star Hotel

Driftwood Inn

Motel in Chestertown MD

5.8

Rated

From $73

$

Info Categories

Dog Friendly Motel

Motel with Parking

Inn at Mitchell House

Bed & Breakfast in Chestertown MD

From $166

$

Info Categories

Bed & Breakfast with Rooms With Fireplace

Bed & Breakfast with Free Wi-Fi

Bed & Breakfast with Parking

Lodging at The Imperial

Hotel in Chestertown MD

9.5

Excellent

$

Info Categories

Family Friendly Hotel

Hotel with Free Wi-Fi

Hotel with Parking

John L Stam House

Accommodation in Chestertown MD

From $211

$

Info

Wren Retweet

Villas in Chestertown MD

$

Info Categories

Dog Friendly Villas

Villas with Free Wi-Fi

Villas with Parking

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

Vacation Home in Chestertown MD

$

Info Categories

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

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

Waterfront Millington Vacation Rental with Hot Tub!

Vacation Home in Chestertown MD

$

Info Categories

Vacation Home with Free Wi-Fi

Vacation Home with Parking

Secluded Cottage in Middle of Chestertown

Apartment in Chestertown MD

$

Info Categories

Dog Friendly Apartment

Apartment with Free Wi-Fi

Apartment with Parking

159 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 Free Wi-Fi

Vacation Home with Parking

3-Star Vacation Home

InnTown House 9.0 km from Chestertown

Apartment in Rock Hall MD

$

Info

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

Vacation Home in Rock Hall MD

$

Info Categories

Vacation Home with Free Wi-Fi

Vacation Home with Parking

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

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

Mariner's Motel 9.4 km from Chestertown

Motel in Rock Hall MD

10

Excellent

$

Info Categories

Dog Friendly Motel

Motel with Swimming Pool

Outdoor Pool

Motel with Free Wi-Fi

Mariners Motel 9.5 km from Chestertown

Accommodation in Rock Hall MD

From $172

$

Info Categories

Dog Friendly Accommodation

Accommodation with Swimming Pool

Outdoor Pool

Accommodation with Free Wi-Fi

Inn at Osprey Point 9.5 km from Chestertown

Inn in Rock Hall MD

9.3

Excellent

From $188

$

Info Categories

Inn with Parking

EV charging stations

Dog Friendly Inn

Inn with Swimming Pool

Private Pool Outdoor Pool

Hotels in Chestertown MD