Pet Friendly Hotels in Chester, MD

There are 2 pet friendly hotels in Chester, and 286 more nearby. Both welcome two or more pets with 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!

£31

+ Pet fee

Big dogs OK

2+ pets OK

VRBO Chester

Chester, MD

VRBO Chester 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 Chester, 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 Chester to collect the pet fee. See Details

£208

+ Pet fee

Big dogs OK

2+ pets OK

Chester Airbnb Rentals

Chester, MD

Chester 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 Chester, please contact the host directly or read the House Rules section at the bottom of their listing. See Details

£99+

No pet fee

Big dogs OK

2+ pets OK

Pet-Friendly Airbnb Rentals

Chester, MD

£46

+$15/night pet fee

40 kg 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. See Details

£83

No pet fee

Big dogs OK

2 pets max

Quality Inn Easton

Easton, MD

Quality Inn Easton Pet Policy Quality Inn Easton welcomes two dogs of any size for no additional fee. Cats are not accepted, and breed restrictions apply. See Details

£130

No pet fee

Big dogs OK

1 pet max

Inn on Main Annapolis

Annapolis, MD

Inn on Main Annapolis Pet Policy Inn on Main Annapolis is pet friendly! One pet of any size is welcome for no additional fee. Both dogs and cats are accepted. Quiet, crated pets may be left unattended in the room. Guests are responsible for any damage or cleaning costs. There is no pet relief area on the property, but there is a park around half a mile away. See Details

£218

+$25/pet/night

Big dogs OK

2+ pets OK

Hummingbird Inn

Easton, MD

Hummingbird Inn Pet Policy Hummingbird Inn allows dogs of any size for an additional fee of $25 per pet, per night. Dogs may not be left in rooms unattended, but the hotel offers a dog sitting service starting at $20 per hour. Dog bowls and trays are available, and leashed dogs can enjoy a grassy pet relief area on the property. Sorry, cats are not accepted. See Details

£53

+$15/night pet fee

40 kg max

2 pets max

Red Roof Inn Annapolis

Annapolis, MD

Red Roof Inn Annapolis Pet Policy Red Roof Inn Annapolis 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. See Details

£158

+$75/night pet fee

Big dogs OK

2 pets max

The Wildset Hotel

St. Michaels, MD

The Wildset Hotel Pet Policy The Wildset Hotel allows 2 dogs of any size in designated rooms for an additional fee of $75 per night. Treats, bowls, and toys are provided at check-in. Sorry, no cats. See Details

£75

+$25/pet/night

20 kg 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. See Details

£124

+$100 pet fee

38 kg 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. See Details

£101

+$75 per pet

32 kg max

2 pets max

Graduate by Hilton Annapolis

Annapolis, MD

Graduate by Hilton Annapolis Pet Policy Graduate by Hilton Annapolis allows 2 pets up to 65 lbs for an additional fee of $75 per pet, per stay. Balcony Rooms are not pet friendly. Both dogs and cats are welcome. Treats are provided at check in. There is a dog park on the property. See Details

£109

+$75 pet fee

45 kg max

2 pets max

Hampton Inn Easton

Easton, MD

Hampton Inn Easton Pet Policy Hampton Inn Easton welcomes two pets up to 90 lbs for an additional fee of $75 (for stays of 1 to 4 nights) and $125 (for longer stays). Both dogs and cats are allowed. See Details

£124

+$50/night pet fee

25 kg max

2 pets max

The Westin Annapolis

Annapolis, MD

The Westin Annapolis Pet Policy The Westin Annapolis allows 2 pets up to 50 lbs in designated rooms for an additional fee of $50 per night. Both dogs and cats are welcome. See Details

£141

+$60/pet/night

Big dogs OK

2 pets max

Wylder Hotel - Tilghman Island

St. Michaels, MD

Wylder Hotel - Tilghman Island Pet Policy Wylder Hotel - Tilghman Island allows 2 dogs of any size for an additional fee of $60 per pet, per night. Pets are not permitted in the pool area or inside dining areas. Sorry, no cats. See Details

£64

+$75 pet fee

Big dogs OK

2 pets max

Sonesta ES Suites Annapolis

Annapolis, MD

Sonesta ES Suites Annapolis Pet Policy Sonesta ES Suites Annapolis allows 2 dogs of any size for an additional fee of $75 for stays of 1 to 7 nights, and $150 for longer stays. There is a pet relief area with waste stations on the property. Please note pets cannot be left unattended in rooms. Sorry, no cats. See Details

£126

+$50 per pet

25 kg max

2 pets max

The Tidewater Inn

Easton, MD

The Tidewater Inn Pet Policy The Tidewater Inn allows 2 dogs up to 50 lbs for an additional fee of $50 per pet, per stay. Crated dogs may be left in the room unattended. Dogs receive homemade treats and bowls upon arrival, and there is a grassy area within walking distance from the hotel. Sorry, no cats. See Details

£147

+$100 pet fee

50 kg max

2 pets max

Annapolis Waterfront Hotel Autograph Collection

Annapolis, MD

Annapolis Waterfront Hotel Autograph Collection Pet Policy Annapolis Waterfront Hotel Autograph Collection welcomes two pets up to 100 lbs in designated rooms for an additional fee of $100 per stay. Both dogs and cats are allowed, but pets may not be left unattended in the room. See Details

£55

+$25/pet/night

Big dogs OK

2 pets max

Village Inn Annapolis MD

Annapolis, MD

Village Inn Annapolis MD Pet Policy Village Inn Annapolis MD welcomes two dogs of any size for an additional fee of $25 per pet, per night. Dogs are only permitted in eight designated rooms, and may not be left in rooms unattended. There is a grassy area for pet relief on the property. Cats are not allowed. See Details

£151

No pet fee

Big dogs OK

2+ pets OK

Sleeps 3

Luxury Flat in Heart of St Michaels

5.0 St. Michaels, MD

Luxury Flat in Heart of St Michaels Pet Policy This 1-bedroom apartment in St. Michaels is pet friendly! Dogs of any size are welcome for no additional fee. Cats may also be allowed by request. See Details

There are 2 pet friendly hotels in Chester, MD. Both welcome two or more pets with no weight limit. Do you know of a pet friendly hotel we've missed? Post a spot to BringFido!