Dog Friendly Hotels, Vacation Homes, Villas, Motels in Chestertown MD

Comfort Inn & Suites Chestertown

Hotel in Chestertown MD

7.6

Good

$

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Dog Friendly Hotel

Hotel for Honeymoon

Business Hotel

Driftwood Inn

Motel in Chestertown MD

5.8

Rated

From $69

$

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Dog Friendly Motel

Motel with Parking

Secluded Cottage in Middle of Chestertown

Apartment in Chestertown MD

$

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Dog Friendly Apartment

Apartment with Free Wi-Fi

Apartment with Parking

Wren Retweet

Villas in Chestertown MD

$

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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

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

58 more hotels nearby!

Great Oak Manor 6.3 mi from Chestertown

Bed & Breakfast in Great Oak Landing MD

9.3

Excellent

From $165

$

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Dog Friendly Bed & Breakfast

Bed & Breakfast with Parking

EV charging stations

Bed & Breakfast with Rooms With Fireplace

Bayside cottage steps from the harbor 9.4 mi from Chestertown

Vacation Home in Rock Hall MD

5.0

Rated

$

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Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

Mariner's Motel 9.4 mi 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 mi from Chestertown

Accommodation in Rock Hall MD

10

Excellent

From $186

$

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Dog Friendly Accommodation

Accommodation with Swimming Pool

Outdoor Pool

Accommodation with Free Wi-Fi

Inn at Osprey Point 9.5 mi from Chestertown

Inn in Rock Hall MD

9.3

Excellent

From $209

$

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Dog Friendly Inn

Inn with Parking

EV charging stations

Inn with Swimming Pool

Private Pool Outdoor Pool

Blake House Historic Estate with Private Inn 11.4 mi from Chestertown

Villas in Centreville MD

$

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Dog Friendly Villas

Villas with Swimming Pool

Outdoor Pool

Villas with Free Wi-Fi

Family-Friendly Cottage, Walk to the Beach! 12.4 mi from Chestertown

Vacation Home in Kennedyville MD

10

Excellent

$

Info Categories

Dog Friendly Vacation Home

Lansdowne Manor 13.4 mi from Chestertown

Vacation Home in Centreville MD

$

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Dog Friendly Vacation Home

Family Friendly Vacation Home

Vacation Home with Free Wi-Fi

Galena House 14.8 mi from Chestertown

Country House in Galena MD

$

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Dog Friendly Country House

Country House with Free Wi-Fi

Country House with Parking

Waterfront Home with Private Beach, Stunning Views 17.3 mi from Chestertown

Vacation Home in Middle River MD

10

Excellent

$

Info Categories

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

Joppatowne Home with Private Deck and Fireplace! 18.0 mi from Chestertown

Vacation Home in Edgewood MD

8.0

Very Good

$

Info Categories

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

Best Western Kent Narrows Inn 18.8 mi from Chestertown

Hotel in Grasonville MD

7.5

Good

From $122

$

Info Categories

Dog Friendly Hotel

Hotel with Rooms With Jacuzzi / Hot-tub

Hotel for Honeymoon

Hilton Garden Inn Kent Island 18.9 mi from Chestertown

Hotel in Grasonville MD

8.3

Very Good

From $210

$

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Dog Friendly Hotel

Hotel Taking Steps Towards Sustainability

Hotel for Honeymoon

Motel 6-Edgewood, MD 19.4 mi from Chestertown

Hotel in Edgewood MD

3.6

Rated

From $67

$

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Dog Friendly Hotel

Hotel near Golf Courses

Hotel with Swimming Pool

Outdoor Pool

Home2 Suites by Hilton Baltimore/Aberdeen MD 19.4 mi from Chestertown

Hotel in Aberdeen MD

8.0

Very Good

From $132

$

Info Categories

Dog Friendly Hotel

Hotel Taking Steps Towards Sustainability

Hotel for Honeymoon

Dog Friendly Hotels in Chestertown MD