Pet Friendly Holiday Rentals in Sudlersville, MD

Pet Friendly Waterfront Retreat with Pool

This 5-bedroom house in Queenstown allows 1 dog of any size for no additional fee. Sorry, no cats.

Mallard House

4.9 Chestertown, MD

Mallard House Pet Policy

This 2-bedroom vacation rental in Chestertown allows 2 dogs under 50 lbs for no additional fee. Cats and larger dogs may also be allowed by request, but all pets must be approved in advance. Pets are not allowed on the furniture. No wet dogs inside. Please bring your own dog towels. The property is not fenced and our dogs and the neighbors' dogs may come over.

Mill Creek River House

5.0 Smyrna, DE

Mill Creek River House Pet Policy

This 3-bedroom house in Smyrna allows 2 dogs of any size for an additional fee of $25 per pet, per stay. Sorry, no cats. There is a dog shower located in the laundry room. A dog door connects to the fenced yard.

Moot Point Farm

5.0 Greensboro, MD

Moot Point Farm Pet Policy

This 2-bedroom vacation rental in Greensboro allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Country Estate in Historic District

5.0 Chestertown, MD

Country Estate in Historic District Pet Policy

This 5-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

The Colonial Farmhouse

5.0 Centreville, MD

The Colonial Farmhouse Pet Policy

This 5-bedroom farm in Centreville allows 2 dogs of any size for an additional fee of $118 per pet, per stay. Cats are also welcome.

Carriage House Hideaway in Middle of Chestertown

5.0 Chestertown, MD

Carriage House Hideaway in Middle of Chestertown Pet Policy

This vacation rental in Chestertown allows 2 dogs under 50 lbs for an additional fee of $20 per pet, per stay. Sorry, no cats.

Cliff Point Retreat

5.0 Chestertown, MD

Cliff Point Retreat Pet Policy

This 3-bedroom vacation rental in Chestertown allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance.

Eastern Shore Beach House

4.7 Betterton, MD

Eastern Shore Beach House Pet Policy

This 6-bedroom vacation rental in Betterton allows dogs of any size for an additional fee of $50 per pet, per stay. Cats may also be allowed by request.

Waterfront Hideaway on Michener's Choptank River

5.0 Greensboro, MD

Waterfront Hideaway on Michener's Choptank River Pet Policy

This 2-bedroom vacation rental in Greensboro allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request.

Historic 12 Acre Waterfront Home with Private Inn

5.0 Centreville, MD

Historic 12 Acre Waterfront Home with Private Inn Pet Policy

This 6-bedroom villa in Centreville allows 3 dogs of any size for an additional fee of $50 per pet, per night. Cats may also be allowed by request.

Historic Stepne Manor on the Eastern Shore

5.0 Chestertown, MD

Historic Stepne Manor on the Eastern Shore Pet Policy

This 5-bedroom house in Chestertown allows dogs of any size for an additional fee of $100 per pet, per stay. Cats may also be allowed by request, but all pets must be approved in advance.

Eagle Point Farm

4.9 Chestertown, MD

Eagle Point Farm Pet Policy

This 4-bedroom vacation rental in Chestertown allows 2 dogs of any size for an additional fee of $150 per pet, per stay. Sorry, no cats.

Private Waterfront Paradise With Pier

5.0 Chestertown, MD

Private Waterfront Paradise With Pier Pet Policy

This 3-bedroom vacation rental in Chestertown allows 2 dogs of any size for an additional fee of $50 per pet, per stay. Sorry, no cats. Dogs are not permitted on the beds or furniture.

Thornton Estate

4.9 Chestertown, MD

Thornton Estate Pet Policy

This 6-bedroom house in Chestertown allows 2 dogs of any size for an additional fee of $100 per pet, per stay. Sorry, no cats. Pets must be approved in advance.

Dover Delight

5.0 Dover, DE

Dover Delight Pet Policy

This 4-bedroom vacation rental in Dover allows 2 dogs of any size for an additional fee of $40 per pet, per stay. Sorry, no cats.

Creek Cottage

5.0 Centreville, MD

Creek Cottage Pet Policy

This 4-bedroom vacation rental in Centreville allows 2 dogs under 60 lbs for an additional fee of $150 per pet, per stay. Breed restrictions may apply. Sorry, no cats.

Pier Pleasure

4.9 Chestertown, MD

Pier Pleasure Pet Policy

Dogs of any size are allowed at this 5-bedroom house in Chestertown for an additional fee of $250 per pet, per stay. Sorry, no cats. Pets are not permitted on the furniture and must be cleaned up after.

Buena Vista

4.7 Betterton, MD

Buena Vista Pet Policy

This 5-bedroom house in Betterton allows 1 dog of any size for an additional fee of $50 per stay. Sorry, no cats. All pets must be approved in advance. Additional pets may be allowed by request.

VRBO Chestertown

Chestertown, MD

VRBO Chestertown Pet Policy

Pet policies are determined by the individual owner of each Vrbo property. For more information on the pet fee, weight limit and other restrictions at a dog-friendly Vrbo in Chestertown, please contact the owner directly or read the 'House Rules' section of their listing. Also be sure to include your pet(s) in the 'Guest' field when making your reservation, so the pet fee can be included. If applicable, it will be usually be displayed in the 'On-site Fees' or 'Owner Fees' sections during checkout. Some owners will also wait until you arrive in Chestertown to collect the pet fee.

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