Book Exclusive Chestertown Vacation Packages

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Chestertown flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD

2 out of 5
Price was CA $975, price is now CA $932 per person
CA $932
per person
Oct 14 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
Stay at this hotel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Price was CA $1,282, price is now CA $1,133 per person
CA $1,133
per person
Oct 14 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maryland Beach and Ocean City Boardwalk are located nearby.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $1,218, price is now CA $1,094 per person
CA $1,094
per person
Oct 14 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
Book a stay at this beach hotel in Fenwick Island. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maryland Beach and Northside Park are located nearby.
Plim Plaza Hotel

Plim Plaza Hotel

2 out of 5
Downtown Ocean City
Price was CA $995, price is now CA $946 per person
CA $946
per person
Oct 14 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was CA $994, price is now CA $946 per person
CA $946
per person
Oct 14 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
Stay at this motel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds are located nearby.

Top Chestertown hotels deals

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Free cancellation
The price is CA $144 per night
CA $144
CA $159 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.
Pool
Breakfast included
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
The price is CA $149 per night
CA $149
CA $170 total
Sep 20 - Sep 21
includes taxes & fees
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive are located nearby.
Pool
Parking included
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
The price is CA $87 per night
CA $87
CA $96 total
Aug 30 - Aug 31
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Larrabee Arts Center are located nearby.
Pet-friendly
Parking included
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
The price is CA $127 per night
CA $127
CA $192 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Annapolis City Dock and Navy-Marine Corps Memorial Stadium are located nearby.
Pet-friendly
Free WiFi
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Free cancellation
Reserve now, pay when you stay
The price is CA $286 per night
CA $286
CA $326 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Annapolis City Dock and Chesapeake Bay Bridge are located nearby.
Pet-friendly
Free WiFi
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Free cancellation
Reserve now, pay when you stay
The price is CA $517 per night
CA $517
CA $665 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Baltimore Inner Harbor Marina and National Aquarium in Baltimore are located nearby.
Pool
Spa
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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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Chestertown Vacations

You don't need to know everything about the place to have an awesome time in Chestertown, but you will need to know a few basic things before you set off.

To help get you oriented, Chestertown sits 30 miles (48 kilometers) east of the well-known city of Baltimore.

This is an area of Eastern Shore that around 5,000 people call home.

Places to visit in Chestertown

Abandon your history books! Let the past jump off the page at Historical Society of Kent County Maryland. Seeking some more options? Great theater can challenge our expectations and asks us to aspire to bigger and better things. Catch a play at Garfield Center for the Arts at the Prince Theater and open your mind to some new ideas. And there's more. You don't need to be a prodigy to admire the vast halls and intriguing past of Washington College.

Where do you fly into for Chestertown?

Slip on your headphones and watch one of the latest in-flight movies. Before long, you'll hit the tarmac at Baltimore Washington International Thurgood Marshall Airport (BWI). It's approximately 30 miles (48 kilometers) to the west from the middle of Chestertown.

Frequently asked questions

How much are vacation packages to Chestertown?
Your vacation fantasies can come to life in Chestertown for as little as CA $932. Our packages include flights and hotels, so you'll find booking is a cinch. The only thing you'll have to worry about is having a good time.
How long should my Chestertown vacation be?
Around 2 nights is the average amount of time travelers spend in Chestertown. But the ideal trip length comes down to how many magical memories you want to make. Why not allow a few extra days and explore some of the lesser-known spots?
Where can I get the best vacation package deals for Chestertown?
For the perfect Chestertown package deal, head straight to Travelocity. Choose from 400 partner airlines and 665,000 properties across the globe to create your ideal trip — it couldn't be easier than that.
Why should I purchase my Chestertown vacation bundle with Travelocity?
The three S's — savings, support and a stress-free booking — are just the beginning. Enjoy a fulfilling travel experience knowing you can rely on round-the-clock support. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.
Can I save on my Chestertown car rental if I bundle it with hotels and flights?
You certainly can — bundle your car, flight and hotel into a Chestertown vacation package and you'll save a ton. With so much to see and do in the Chestertown area, that rental car will more than come in handy. Once you've buckled up, put the stereo on and make tracks to White House, a renowned attraction around 90 kilometersfrom Chestertown.
What is the best time of year to go to Chestertown?
You'll pick up the cheapest hotel prices in and pay more in . You can expect it to be quieter in , while there'll be more fellow visitors to meet during . It comes down to what prices you're willing to pay, the climate and how you deal with crowds.
Which airport is best for Chestertown?
One of the most convenient options is Washington, DC (DCA-Ronald Reagan Washington National), which is located 90 kilometerssouthwest of the hustle and bustle of downtown Chestertown. You can also jet into Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), 50 kilometersaway from central Chestertown).
What is there to do in Chestertown?
Washington College is one of the memorable sights that make Chestertown a popular place to visit. But give yourself enough time to roam its lesser-known attractions too. This is sometimes where the best memories are created.
Where should I stay when visiting Chestertown?
Many visitors stay at the Holiday Inn Express Hotel & Suites Chestertown. It's an excellent base for your Chestertown getaway.
Can I go on vacation to Chestertown at this time?
Don't plan your trip to Chestertown without up-to-date facts about travel restrictions and quarantine policies. Travelocity's Covid-19 Travel Advisor will fill you in. It has all the information you need to make your getaway as relaxed as possible.

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.