Pet Friendly Hotels in Chestertown, MD

There are 13 pet friendly hotels in Chestertown. All of them welcome two or more pets, and 9 have no weight limit. Need help to decide where to stay with your dog? Browse the results below and filter by amenities to find the perfect spot. BringFido members never pay a booking fee, and their reservations are backed by our Pet Friendly Guarantee!

$70

+$15/night pet fee

80 lbs max

2 pets max

Red Roof Inn & Suites Chestertown

Chestertown, MD

Red Roof Inn & Suites Chestertown Pet Policy

Red Roof Inn & Suites Chestertown allows 1 pet up to 80 lbs for no additional fee, and 2 pets up to 80 lbs for $15 per night (not to exceed $105 per stay). Both dogs and cats are welcome, but pets may not be left in the room unattended. There is a pet relief area on the property.

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$107

+$25/pet/night

40 lbs max

2 pets max

Comfort Inn & Suites Chestertown

Chestertown, MD

Comfort Inn & Suites Chestertown Pet Policy

Comfort Inn & Suites Chestertown welcomes two pets up to 40 lbs for an additional fee of $25 per pet, per night. Both dogs and cats are accepted, but four-legged guests must be crated when left in rooms unattended. Pet bowls are available upon request. Grassy pet relief areas with waste stations can be found in front of and behind the hotel.

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$99+

No pet fee

Big dogs OK

2+ pets OK

Pet-Friendly Airbnb Rentals

Chestertown, MD

$442

No pet fee

50 lbs max

2 pets max

Sleeps 6

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.

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$356

+$20/pet/night

Big dogs OK

2+ pets OK

Brampton Bed and Breakfast Inn

Chestertown, MD

Brampton Bed and Breakfast Inn Pet Policy

Brampton Bed and Breakfast Inn welcomes dogs of any size in designated rooms for an additional fee of $20 per pet, per night. Only the Apartment and Russell's Cottage are pet friendly. There will be freshly prepared homemade biscuits from our pastry chef awaiting your arrival. We will also provide you with a water bowl, towels and pet blankets for your dogs to use. For the safety and enjoyment of our other guests, pets are not allowed in the manor house. We will gladly include a breakfast delivery to the Apartment as an extra perk during your stay. Dogs must be crated if left unattended.

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$63

+$25/pet/night

Big dogs OK

2 pets max

Driftwood Inn

Chestertown, MD

Driftwood Inn Pet Policy

Driftwood Inn welcomes two pets of any size for an additional fee of $25 per pet, per night.

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$185

+$20 per pet

50 lbs max

2 pets max

Sleeps 2

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.

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$375

+$50 per pet

Big dogs OK

2+ pets OK

Sleeps 8

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.

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$230

+$50 per pet

Big dogs OK

2+ pets OK

Sleeps 10

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.

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$427

+$50 per pet

Big dogs OK

2 pets max

Sleeps 10

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.

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$990

+$100 per pet

Big dogs OK

2 pets max

Sleeps 13

Thornton Estate

5.0 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.

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$43

+ Pet fee

Big dogs OK

2+ pets OK

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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$612

+$136 pet fee

Big dogs OK

3 pets max

Home on Chester River With Dock

Chestertown, MD

Home on Chester River With Dock Pet Policy

This cottage in Chestertown allows 3 pets of any size for an additional fee of $136 per stay. Both dogs and cats are welcome.

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$171

+ Pet fee

Big dogs OK

2+ pets OK

Chestertown Airbnb Rentals

Chestertown, MD

Chestertown Airbnb Rentals Pet Policy

Pet policies are determined by the individual host of each Airbnb property. For more information on the pet fee, weight limit, and other restrictions at a particular property in Chestertown, please contact the host directly or read the House Rules section at the bottom of their listing.

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$169

+$100 pet fee

75 lbs max

2 pets max

Hyatt Place Kent Narrows & Marina

Grasonville, MD

Hyatt Place Kent Narrows & Marina Pet Policy

Hyatt Place Kent Narrows & Marina welcomes one dog up to 50 lbs or two dogs with a combined weight up to 75 lbs for an additional fee of $100 (for stays of 1 to 6 nights) and $200 (for longer stays). Sorry, no cats.

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$80

+$25 pet fee

50 lbs max

2 pets max

Extended Stay America Suites Baltimore Bel Air Aberdeen

Bel Air, MD

Extended Stay America Suites Baltimore Bel Air Aberdeen Pet Policy

Extended Stay America Suites Baltimore Bel Air Aberdeen allows 2 pets up to 50 lbs for an additional fee of $25 per pet, per night up to the first 6 nights and $15 per pet, per night thereafter. Larger pets are considered with prior approval from the hotel, but pets can be no longer than 36 inches and no taller than 36 inches. Both dogs and cats are allowed.

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$123

+$60 pet fee

50 lbs max

2 pets max

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville, MD

Holiday Inn Express Annapolis East-Kent Island by IHG Pet Policy

Holiday Inn Express Annapolis East-Kent Island by IHG allows 2 pets up to 50 lbs for an additional fee of $60 per stay. Both dogs and cats are welcome.

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$86

+$25/pet/night

80 lbs max

2 pets max

Candlewood Suites Aberdeen-Bel Air by IHG

Bel Air, MD

Candlewood Suites Aberdeen-Bel Air by IHG Pet Policy

Candlewood Suites Aberdeen-Bel Air by IHG welcomes two pets up to 80 lbs for an additional fee of $25 per pet, per night. Both dogs and cats are accepted. Quiet, crated pets may be left in the room unattended. There are treats at the front desk and a dog walking area with a pet station and water on the property.

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$79

+$25/pet/night

75 lbs max

2 pets max

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Edgewood, MD

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A Pet Policy

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A allows 2 pets up to 75 lbs for an additional fee of $25 per pet, per night (not to exceed $75 per stay). Both dogs and cats are welcome, but pets cannot be left unattended in rooms. There is a small grassy pet relief area with waste station on the property.

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$109

+$75 per pet

75 lbs max

2 pets max

Hilton Garden Inn Aberdeen

Aberdeen, MD

Hilton Garden Inn Aberdeen Pet Policy

Hilton Garden Inn Aberdeen allows 2 dogs up to 75 lbs for an additional fee of $75 per pet, per stay, and 2 dogs over 75 lbs for $125 per pet, per stay. Both dogs and cats are welcome.

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There are 13 pet friendly hotels in Chestertown, MD. All of them welcome two or more pets, and 9 have no weight limit. Do you know of a pet friendly hotel we've missed? Post a spot to BringFido!