Chestertown Hotel Guide - Pet Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Pet Friendly Hotels

Our top choices for Chestertown pet-friendly hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (898 reviews)
"Best place to stay always "
United States
Robert
The price is €104
includes taxes & fees
26 Apr - 27 Apr
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (435 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is €67
includes taxes & fees
20 Apr - 21 Apr
Red Roof Inn & Suites Chestertown
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is €305
includes taxes & fees
14 Apr - 15 Apr
Bayside Cottage steps from Rock Hall Harbor
Interior

Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood
Arnold
9.4 out of 10, Exceptional, (38 reviews)
"Super clean place, great communication from the host, and home is exactly as described and shown in pictures. "
United States
Traci L.
The price is €283
includes taxes & fees
14 Apr - 15 Apr
Large 2 bedroom house with private parking in a nice neighborhood
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (13 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is €83
includes taxes & fees
16 Apr - 17 Apr
Charming 2-bedroom house in Aberdeen with WiFi and AC
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is €479
includes taxes & fees
19 Apr - 20 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Smart TV, printers

Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
9.8 out of 10, Exceptional, (6 reviews)
"House kept very clean and neighborhood was really quiet at night! Will be staying again."
United States
Pai’Syn
The price is €245
includes taxes & fees
16 Apr - 17 Apr
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (541 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is €128
includes taxes & fees
14 Apr - 15 Apr
Vandiver Inn
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
The price is €365
includes taxes & fees
14 Apr - 15 Apr
18th Cent. Charm in Historic Downtown Annapolis
Interior

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is €617
includes taxes & fees
14 Apr - 15 Apr
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4/10 Poor
"No microwave, no towel hangers the best thing was the shops and restaurants nearby"
Steven 2-night trip
Posted 10 hours ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Two other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn.
What's the best time of year to travel to Chestertown with my pet?
When you travel with your pet, keeping tabs on the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What is there to see and do with your pet in Chestertown?
Known for its sports, Chestertown has lots to offer visitors, including its university life and festivals. See the local sights and visit Garfield Center for the Arts at the Prince Theater and Rolphs Wharf Marina. While you're there, make sure you don't miss Northern Chesapeake Bay and Chesapeake Bay.