Hotels, Vacation Homes, Apartments, Motels in Chestertown MD

Brampton 1860

Bed & Breakfast in Chestertown MD

9.4

Excellent

From $334

$

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Small Bed & Breakfast

Bed & Breakfast with Parking

EV charging stations

Boutique-style Bed & Breakfast

Lodging at The Imperial

Hotel in Chestertown MD

9.5

Excellent

$

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Family Friendly Hotel

Hotel with Free Wi-Fi

Hotel with Parking

Quality Suites

Hotel in Chestertown MD

$

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Hotel with Swimming Pool

Hotel with Free Wi-Fi

3-Star Hotel

Comfort Inn & Suites Chestertown

Hotel in Chestertown MD

8.0

Very Good

$

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Hotel near Golf Courses

Hotel for Honeymoon

Dog Friendly Hotel

Driftwood Inn

Motel in Chestertown MD

4.8

Rated

From $69

$

Info Categories

Dog Friendly Motel

Carriage House Hideaway In Center of Chestertown

Apartment in Chestertown MD

9.7

Excellent

$

Info Categories

Dog Friendly Apartment

Wren Retweet

Villas in Chestertown MD

$

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Dog Friendly Villas

Pet-Friendly Home on Chester River with Dock!

Vacation Home in Chestertown MD

$

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Dog Friendly Vacation Home

Vacation Home with Swimming Pool

Outdoor Pool

Vacation Home with Free Wi-Fi

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

Vacation Home in Chestertown MD

$

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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

$

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3-Star Vacation Home

River Heights Retreat

Vacation Home in Chestertown MD

$

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Dog Friendly Vacation Home

4-Star Vacation Home

172 more hotels nearby!

Oakley Acre 7.9 km from Chestertown

Apartment in Kennedyville MD

$

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Apartment with Free Wi-Fi

Apartment with Parking

Eastern Shore Getaway Walk to Tolchester Marina! 8.8 km from Chestertown

Vacation Home in Rock Hall MD

$

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3-Star Vacation Home

Twin Ponds Lodge 10.6 km from Chestertown

Vacation Home in Centreville MD

$

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Vacation Home with Free Wi-Fi

Vacation Home with Parking

Rock Hall Retreat with Balcony Near Park and Marina! 10.8 km from Chestertown

Vacation Home in Rock Hall MD

$

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Vacation Home with Free Wi-Fi

Vacation Home with Parking

3-Star Vacation Home

Family-Friendly Cottage, Walk to the Beach! 11.2 km from Chestertown

Vacation Home in Kennedyville MD

10

Excellent

$

Info Categories

Dog Friendly Vacation Home

Mariner's Motel 11.2 km from Chestertown

Motel in Rock Hall MD

9.4

Excellent

$

Info Categories

Dog Friendly Motel

Motel with Swimming Pool

Outdoor Pool

Motel with Parking

Bayside cottage steps from the harbor 11.2 km from Chestertown

Vacation Home in Rock Hall MD

5.0

Rated

$

Info Categories

Dog Friendly Vacation Home

Vacation Home with Parking

Mariners Motel 11.2 km from Chestertown

Accommodation in Rock Hall MD

10

Excellent

From $172

$

Info Categories

Dog Friendly Accommodation

Accommodation with Swimming Pool

Outdoor Pool

Accommodation with Free Wi-Fi

Hotels in Chestertown MD