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Flight Info
Destination airport
Chestertown

Flights To Chestertown

Once you’ve decided where to go on your next holiday, the fun part begins! Wotif makes it easy (and yes, even fun!) to compare flights to Chestertown, so you can get the best deals and save that dough for exploring your new favourite place. Speaking of exploring, it’s time to start planning your itinerary. Whether you love off-the-beaten-path neighbourhoods or busy shopping and dining districts, you’re sure to find what you’re looking for. Hit up top-rated restaurants and hidden local haunts, snap some photos of historic landmarks and make a few friends along the way—starting with your aisle mate on the plane.

No matter where you call home, we’ve got Chestertown flights that will get you from point A to point B in style and comfort. Ready to start packing? It’s OK to be “that passenger” in your matching tracksuit and eye mask, snoozing right up until the final descent. After all, nothing says “holiday” more than a good nap! If you don’t want to surrender a second of your trip to sleep, grab a cup of coffee and chat with fellow travellers or plug in to a flick that takes place in your destination city—it’s like cultural anthropology. For science!

OK, traveller. Let’s do this. Sweet plans? Tick. Craving for adventure? You got it. Entertainment for the flight? Packed. Cheap flights to Chestertown? Book them with Wotif for great deals on travel that fits your schedule and airlines that fit your price range. And last but not least, unforgettable holiday memories? They’re already in the works!

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Hotels in Chestertown

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
The price is AU$336 per night from 29 Dec to 30 Dec
AU$336
29 Dec - 30 Dec
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, a rooftop terrace and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (886 reviews)
Lovely hotel, my favorite place to stay in Annapolis!

Reviewed on 21 Dec 2025

Annapolis Waterfront Hotel, Autograph Collection
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
The price is AU$631 per night from 22 Jan to 23 Jan
AU$631
22 Jan - 23 Jan 2026
includes taxes & fees
Stay at this luxury hotel in Baltimore. Enjoy free Wi-Fi, an outdoor pool and 2 bars/lounges. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.2/10 Wonderful! (1,000 reviews)
Really nice cozy room we had the terrace balcony would definitely stay again!

Reviewed on 9 Dec 2025

Pendry Baltimore
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,904 reviews)
Great customer service!

Reviewed on 21 Dec 2025

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.

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^Savings based on all package bookings made with Flight + Hotel on Wotif.com from , as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.