Pet Friendly Hotels & Resorts in Chestertown from AU$105

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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, (899 reviews)
"Best place to stay always "
United States
Robert
The price is AU$170
includes taxes & fees
3 May - 4 May
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 AU$110
includes taxes & fees
29 Apr - 30 Apr
Red Roof Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is AU$105
includes taxes & fees
18 Apr - 19 Apr
Driftwood Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is AU$168
includes taxes & fees
19 Apr - 20 Apr
Best Western Kent Narrows Inn
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (542 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is AU$210
includes taxes & fees
19 Apr - 20 Apr
Vandiver Inn
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 AU$463
includes taxes & fees
20 Apr - 21 Apr
Large 2 bedroom house with private parking in a nice neighborhood
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 AU$499
includes taxes & fees
4 May - 5 May
Bayside Cottage steps from Rock Hall Harbor
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (14 reviews)
"Met our needs. Great stay."
United States
Robert C.
The price is AU$132
includes taxes & fees
23 Apr - 24 Apr
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 AU$552
includes taxes & fees
19 Apr - 20 Apr
18th Cent. Charm in Historic Downtown Annapolis
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 AU$396
includes taxes & fees
19 Apr - 20 Apr
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

2/10 Terrible
"Do not book with this hotel, if you have already then cancel it -- it's worth paying a cancelation fee to not stay here. There's no elevator, ice machines are out of order, there was an exterior door in the guest area that didn't close. Our room had dirty towels, no body soap, and a broken TV. Any positive reviews must be bots or affilated with management because this place deserves to go out of business asap. "
Sebastian 2-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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 Historical Society of Kent County Maryland and Rolphs Wharf Marina. While you're there, make sure you don't miss Northern Chesapeake Bay and Chesapeake Bay.