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Plim Plaza Hotel

Plim Plaza Hotel

2 out of 5
Downtown Ocean City
Price was $1,195, price is now $986 per person
$986
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
This smoke-free hotel features 3 restaurants, a bar/lounge, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A terrace, a picnic area, and free newspapers are also on offer.
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $1,894, price is now $1,423 per person
$1,423
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $1,684, price is now $1,283 per person
$1,283
per person
Sep 30 - Oct 4
found 1 day 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.
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Price was $1,365, price is now $1,071 per person
$1,071
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Free WiFi in public areas is available at this apartment. Take advantage of the free self parking.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $2,476, price is now $2,042 per person
$2,042
per person
Sep 30 - Oct 4
found 1 day 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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Free Cancellation
$103 nightly
The price is $115 total per night
$115 total
Aug 23 - Aug 24
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.
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
$124 nightly
The price is $137 total per night
$137 total
Jul 28 - Jul 29
Total with taxes and fees
A golf course and a 24-hour gym are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A picnic area, laundry facilities, and barbecue grills are also on offer.
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
$63 nightly
The price is $70 total per night
$70 total
Aug 2 - Aug 3
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.
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $168 total per night
$168 total
Aug 10 - Aug 11
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.
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
$450 nightly
The price is $529 total per night
$529 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.
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
$74 nightly
The price is $85 total per night
$85 total
Aug 23 - Aug 24
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.
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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 $986. 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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