Photo by Assya A

Search Chestertown hotels

Most accommodation are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Filter by

Popular filters
Popular filters
Total price
Guest rating
Guest rating
Property class
Payment type
Payment type
Property type
Property type
Area
Area
Popular locations
Popular locations
Meal plans available
Meal plans available
Amenities
Amenities
Accessibility
Accessibility
Traveller experience
Traveller experience

Top hotels and accommodation in Chestertown

More cheap accommodation in Chestertown

Stay near top Chestertown attractions

Chestertown hotels information

Number of reviews
6,040
Accommodation
994 hotels
Lowest Price
NZ$130
Highest Price
NZ$657

Frequently asked questions

Where is the best place for a stay in Chestertown?

Comfort Inn & Suites Chestertown is a favourite property for Expedia customers. This hotel offers free breakfast and free parking. Red Roof Inn & Suites Chestertown is another top choice for your stay based on reviews. See all available top hotels, or vacation rentals in Chestertown.

What are some of the best holiday rentals that Chestertown has to offer?

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!: This holiday home rental outside of Chestertown is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. See all vacation rentals in Chestertown.

If I need to cancel my hotel reservation in Chestertown, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.

What's the best accommodation for a budget-friendly stay in Chestertown?

Based on reviews, Red Roof Inn & Suites Chestertown is a popular 2-star hotel for our travellers looking for an economical choice, and features free WiFi and free parking. Another top choice for your budget-friendly stay is Driftwood Inn. View all budget hotels in Chestertown.

What's the best accommodation option for a family holiday in Chestertown?

Red Roof Inn & Suites Chestertown is a hotel with free parking and laundry facilities, and it's a top choice on Expedia for families. Driftwood Inn is another choice for your stay with the kids. Also, children of all ages will enjoy a visit to Crumpton Auction. Find more child-friendly accommodations in Chestertown.

What's the best place to stay for couples in Chestertown?

Red Roof Inn & Suites Chestertown is a favourite hotel for couples, and features free WiFi and free parking. See all romantic hotels in Chestertown.

What's the best pet-friendly accommodation option in Chestertown?

Driftwood Inn is a top property for people travelling with their pets and offers free WiFi for its human guests. Comfort Inn & Suites Chestertown is another good option for you and your pet. See more pet-friendly hotel accommodations in Chestertown.

What's the best hotel to stay near the beach in Chestertown?

Great Oak Manor is a top B&B located on the beach . See more stays near the beach in Chestertown.

What's the best hotel in Chestertown to learn about local history?

Based on our travel expertise, Comfort Inn & Suites Chestertown is a top hotel on Expedia for those interested in history, and it features free breakfast and free WiFi. Also, notable landmarks to visit include Historical Society of Kent County Maryland. See more options for historical stays in Chestertown.

What are some accommodation options with pools in Chestertown?

Sagamore Pendry Baltimore: Hotel located near Baltimore Inner Harbor Marina. Provides a full-service spa, a seasonal outdoor pool and 2 bars. Hampton Inn Baltimore Bayview Campus and Best Western Plus Hotel & Conference Center are a couple of other choices that feature an on-site pool. View all hotels with pools in Chestertown.

What is the best spa hotel in Chestertown?

Great Oak Manor is a top spa hotel featuring a private beach and a fitness centre. See all spa hotels in Chestertown.

How is it to stay in Chestertown?

Visitors to Chestertown will definitely enjoy the university setting. Tourists can also enjoy the city's sporting events, festivals and art. In Chestertown, there are 43 hotels and other accommodation options to choose from. Find out more about Chestertown.

Recent Reviews in Chestertown
Expedia verified reviews