The Best Hotels with Restaurants in Chestertown, MD from $89 in 2024

Check availability on Chestertown Hotels with Restaurants

Pick from 5 Chestertown Hotels with Restaurants and compare room rates, reviews, and availability. Most hotels are fully refundable.

"Plenty of privacy "

"Super nice and friendly front desk staff. The room was very clean and spacious (suite). I’ve had less than positive experiences at other Comfort Inns, but this one is the exception. I’d absolutely stay here again!"

$126 total

includes taxes & fees

May 5 - May 6

Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

"This is a conveniently located and comfortable Inn/Hotel. It was perfect for a one night stay. The only deficit was the lack of a simple, continental breakfast room necessitating a walk to the local DD/Dunkin'."

$99 total

includes taxes & fees

May 21 - May 22

Chestertown Hotels with Restaurants information

Hotels with Restaurants in Chestertown	5
Highest price	$114
Cheapest price	$89
Number of guest reviews	968
Total number of hotels in Chestertown	996

Frequently asked questions

How much do hotels with dining in Chestertown cost?

Hotels in Chestertown range between $89 to $114 per night. Bring your appetite — these stays have restaurants or offer access to some great dining experiences. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Are there any family-friendly hotels with dining in Chestertown?

Many visitors seeking a family-friendly hotel with dining in Chestertown pick Comfort Inn & Suites Chestertown. With a 2.5-star rating and amenities including a swimming pool and complimentary breakfast, it’ll get your crew’s nod of approval. Red Roof Inn & Suites Chestertown is a 2-star stay that will also place you within easy reach of some delicious dining experiences. Laundry facilities and front desk services help make it a comfy base for your family getaway. Chestertown has loads of family-friendly attractions to discover when you need to keep the kids busy. River Arts Chestertown and Historical Society of Kent County Maryland guarantee fun for travelers young and old.

Why book your hotel with dining in Chestertown with Expedia?

Whether you’re after a hotel with a restaurant, or one that’s close to a foodie hot spot, Expedia will have a stay that suits your tastes. Use our handy filters to search for Chestertown hotels with on-site dining. You can also search for properties in desired locations full of cafés, restaurants or markets. Whatever suits your style, you’ll always score a delectable deal with Expedia!

How can I find cheap hotels with dining in Chestertown?

With Expedia’s nifty filter tool, scoring cheap hotels with dining in Chestertown couldn’t be simpler. To view accommodations that are easy on your bank balance, narrow down your search by meal plans, budget and star rating.

What is there to do in Chestertown near my hotel with dining?

If you’re eager to experience the best of Chestertown, Historical Society of Kent County Maryland is the perfect place to start.