Chestertown Holidays

Book a Hotel + Flight or Car together to unlock savings

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Our pick of the best Chestertown Hotel Deals

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$141 per night from 22 May to 23 May
NZ$141
per night
22 May - 23 May
7.2/10 Good! (264 reviews)
"Hotel was a hotel… hated the small toilets… if you go to wipe your hand will end up touching the water.. yuck! If you’re a man and have to poop…. hold your junk up!!!"

Reviewed on 13 May 2024

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is NZ$226 per night from 16 May to 17 May
NZ$226
per night
16 May - 17 May
8.4/10 Very Good! (671 reviews)
"The onsite manager was very helpful. The staff was very nice."

Reviewed on 13 May 2024

Comfort Inn & Suites Chestertown
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$322 per night from 28 May to 29 May
NZ$322
per night
28 May - 29 May
8.8/10 Excellent! (1,612 reviews)
"The location was excellent, the room wss very nice bit was decorated in a fashion that was too modern give the name of the hotel. The staff was friendly and efficient but said they would send an Anniversary present to our room but it never arrived. The facility was good but the elevator was too ..."

Reviewed on 9 May 2024

Historic Inns of Annapolis
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.

Frequently asked questions

How much does a Chestertown holiday package cost?
The most affordable Chestertown package is , so your dream getaway can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to tailor a package suited to your travel style.
How do I get a cheap travel package to Chestertown?
Browse and lock in everything all in one place with our Chestertown holiday packages. You’ll find deals on hotels, flights, tours and more that’ll keep your wallet happy and your adventurous spirit busy. And, with more than 550 air carriers and 1 000 000 hotels across the globe to select from, you’ll have endless opportunities to mix and match your own way.
Where should I stay in Chestertown?
Stay close to the action. Many people book hotels within easy reach of popular sights, such as Washington College, Rolphs Wharf Marina and River Arts Chestertown.
What are the top hotels in Chestertown?
If it’s your first time staying in Chestertown, reserve a room at Circa 1900 Home In The Heart Of Historic Downtown Chestertown or Historic Downtown Chestertown Home. #1 Location. Both have good amenities and are favourites among many savvy travellers.
How far in advance should I book my Chestertown holiday?
To score cheap prices, book ASAP. Airlines usually start selling tickets, along with some of the lowest fares, up to a year prior to departure. Hotels, experiences and car rental should also be booked well in advance to avoid disappointment. If you’ve decided on a last-minute getaway in Chestertown, there are always lots of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Chestertown travel package include?
Much of that depends on you. You can select from a range of Chestertown bundles, such as a flight, hotel and rental car. You can also book a flight and a hotel, or a rental car with a flight. Once you’ve made your booking, you can add the fun stuff like tours and activities. Whatever your perfect Chestertown holiday looks like, you’ll save!
What should I know before booking a Chestertown travel package?
When you book your hotels, flights and car rentals together, you’ll score great discounts. Whether you’re organising a rural escape in a cottage or want to stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Chestertown Expedia holiday package?
Definitely. Expedia has over 550 partner airlines to choose from all over the world. With all that choice at your fingertips, finding the right carrier to get you to Chestertown will be easy.
If I'm not able to travel, can I cancel my Chestertown holiday package?
Don’t worry if you’re rethinking your Chestertown holiday package — it’s possible to change or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We understand life can sometimes throw a spanner in the works, so head to our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll be here to help.

Discover the most popular places to visit in Chestertown

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.