Deals on vacations and trips to Chestertown

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Chestertown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
OCHG Beachviews

OCHG Beachviews

2 out of 5
Downtown Ocean City
Price was $872, price is now $808 per person
$808
per person
Nov 8 - Nov 12
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $2,745, price is now $2,060 per person
$2,060
per person
Nov 8 - Nov 12
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
This hotel features free self parking and express check-in. Express check-out is also provided.
The Shore House

The Shore House

2 out of 5
West Ocean City
Price was $2,566, price is now $2,090 per person
$2,090
per person
Nov 8 - Nov 12
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A seasonal outdoor pool and laundry facilities are also provided.
Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $970, price is now $839 per person
$839
per person
Nov 8 - Nov 12
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
This aparthotel features a seasonal outdoor pool and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. Dry cleaning and laundry facilities are also provided.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,241, price is now $1,103 per person
$1,103
per person
Nov 8 - Nov 12
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Chestertown hotels deals

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $80 total per night
$80 total
Oct 13 - Oct 14
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, laundry facilities, and free newspapers are also on offer.
Pet friendly
Parking included
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
$124 nightly
The price is $137 total per night
$137 total
Oct 8 - Oct 9
Total with taxes and fees
A golf course, 2 restaurants, and a 24-hour gym are all featured at this smoke-free lodge. Dine at the beachfront restaurant and relax with sun loungers. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Pool
Parking included
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $121 total per night
$121 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $81 total per night
$81 total
Oct 12 - Oct 13
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$125 nightly
The price is $143 total per night
$143 total
Nov 4 - Nov 5
Total with taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A terrace, limo/town car service, and a garden are also on offer.
Pet friendly
Free WiFi
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $136 total per night
$136 total
Oct 11 - Oct 12
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
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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.

Stay near popular Chestertown attractions

Washington College

8.6/10 (87 reviews)
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Frequently asked questions

How much are vacation packages to Chestertown?
Travelocity provides package deals to Chestertown, including hotels and flights, starting from an impressive $808. With the cash you save, you could purchase some cool tours or perhaps even add on a few extra nights to your exciting getaway.
How long should my Chestertown vacation be?
Your Chestertown trip can be as short or as long as you want, but most people stay around 2 nights. Like to hop off the beaten path and discover some less touristy sights? Book a few extra nights and experience another side of this place.
Where can I get the best vacation package deals for Chestertown?
There are incredible Chestertown package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties all over the world? Remember this when you're ready to tick another destination off your must-visit list.
Why should I book my Chestertown vacation bundle via Travelocity?
Whether you're in search of the ultimate unplugged getaway or after the fun and excitement of the big smoke, booking everything with Travelocity saves you time, hassle and money. No need to sift through hundreds of different websites looking for the best deal — our Price Match Guarantee ensures you'll never be out of pocket, and our team of customer service experts are available for you round-the-clock.
Will I save money on my Chestertown car rental if I combine it with my hotel or flight?
With a Chestertown vacation package, you can bundle your hotel, car and flight bookings and save loads. When you're ready to discover the best of this exciting location, why not check out White House? This famous attraction is 55 mi from Chestertown. With your own rental car, you'll be there in a jiffy.
What is the best time of year to go to Chestertown?
You'll pick up the cheapest hotel prices in and pay the highest prices during . You can usually expect it to be less busy in May, November and December, while you'll find more fellow travelers to meet during the months of February, March and October. It all comes down to what prices you're willing to pay, the weather and how well you handle crowds.
Which airport is best for Chestertown?
Ronald Reagan Washington National Airport (DCA), 60 mi southwest of the city center, is where many visitors start their adventures in Chestertown. That said, Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (30 mi away from central Chestertown) could be more convenient for you.
What is there to do in Chestertown?
While venturing off the beaten track can be rewarding, you shouldn't ignore the popular attractions that make a place famous. Washington College and River Arts Chestertown are a couple of them in Chestertown.
Where should I stay when visiting Chestertown?
If you're after somewhere to lay your head, take a look at the Comfort Inn & Suites Chestertown. It's the top choice for many travelers.

Photos of local treasures

Browse Chestertown vacation photos for more inspiration

An aerial view of a town with a river, buildings, and surrounding greenery.
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.
A riverside residential area with houses, docks, and a clear blue sky.
A riverside town with red brick buildings, a dock, and autumn foliage.
A calm lake with a sailboat, trees, and a house on the shore.

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