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How Much Does it Cost To Fly To Chestertown?
Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$2,901 Return, found 1 day ago
NZ$2,901
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$2,901 Return, found 1 day ago
NZ$2,901
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$2,921 Return, found 1 day ago
NZ$2,921
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$2,921 Return, found 1 day ago
NZ$2,921
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$2,953 Return, found 1 day ago
NZ$2,953
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$2,971 Return, found 1 day ago
NZ$2,971
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$3,021 Return, found 1 day ago
NZ$3,021
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$3,153 Return, found 1 day ago
NZ$3,153
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$3,171 Return, found 1 day ago
NZ$3,171
Return
found 1 day ago

Mon, 25 Jan - Sun, 31 Jan
AKL
Auckland
BWI
Baltimore
NZ$3,205 Return, found 1 day ago
NZ$3,205
Return
found 1 day ago
Destination airport | Baltimore Washington Intl. Thurgood Marshall |
|---|---|
Destination city name | Baltimore |
Return price | NZ$2,900 |
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Compact
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Midsize
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SUV
Jeep Compass or similar

Hotels in Chestertown

Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
The price is NZ$213 per night from 12 Apr to 13 Apr
NZ$213
12 Apr - 13 Apr
includes taxes & fees
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (891 reviews)
Frindly staff. Slight noise but not bad. Rooms clean and comfortable.
Reviewed on 25 Mar 2026

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown MD
Stay at this cabin in Chestertown. Enjoy a garden, laundry facilities and patios. Popular attractions Chase Island and Crumpton Auction are located nearby.
10/10 Exceptional! (16 reviews)
We brought our Lab with us. She loved looking out all the windows. She was afraid to walk up the open stairs but was content to sleep on the first floor. We enjoyed our stay at Outrange. Very quiet and secluded. Short walk to River.
Reviewed on 22 Mar 2026

Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is NZ$283 per night from 2 Apr to 3 Apr
NZ$283
2 Apr - 3 Apr
includes taxes & fees
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 ...
9/10 Wonderful! (1,862 reviews)
Clean room, friendly staff, and the PERFECT location for walking downtown Annapolis.
Reviewed on 24 Mar 2026
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.co.nz 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.