Kent County Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Kent County

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
20 W Baltimore St Baltimore MD
The price is S$170 per night from 4 Aug to 5 Aug
S$170
4 Aug - 5 Aug
includes taxes & fees
Lord Baltimore Hotel
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is S$168 per night from 20 Aug to 21 Aug
S$168
20 Aug - 21 Aug
includes taxes & fees
8.8/10 Excellent! (1,046 reviews)
"everything was perfect. Just the bathroom needs better cleaning overall it was great"

Reviewed on 21 Jul, 2026

DoubleTree by Hilton Hotel Annapolis
Hyatt Regency Baltimore Inner Harbor

Hyatt Regency Baltimore Inner Harbor

4 out of 5
300 Light Street Baltimore MD
The price is S$257 per night from 5 Aug to 6 Aug
S$257
5 Aug - 6 Aug
includes taxes & fees
Hyatt Regency Baltimore Inner Harbor
See all 2,396 properties in Kent County
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.

Frequently asked questions

How much does a Kent County holiday package cost?
We make it simple to travel somewhere new, with Kent County packages starting from as little as . You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate getaway, why not add a few activities and tours to your travel itinerary?
How do I get a cheap travel package to Kent County?
Creating your own Kent County holiday package with Expedia is one of the easiest ways to save. We offer more than 550 air carriers and 1,000,000 hotel options around the globe. With such a huge range to choose from, you'll have no worries putting together your ideal getaway.
What are the top hotels in Kent County?
Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown know how to make their guests feel welcome in Rock Hall. If you also plan to explore Chestertown, check out Driftwood Inn and Mariners Motel. Both are very popular with travellers.
How far in advance should I book my Kent County holiday?
Smart travellers often book early. You can normally start comparing international fares on Expedia up to a year before your intended flight. If you've left booking to the last minute, don't worry. Bargain prices sometimes occur just weeks before departure.
What does an Expedia Kent County travel package include?
With Expedia, you can choose any combination of car rentals, hotels and flights to build your perfect Kent County travel package. Once you've made your booking, you can add on the fun stuff like day tours and activities. Don't forget — the more you bundle, the greater the savings!
What should I know before booking a Kent County travel package?
So many places to wander around, so many things to do. With a travel package, you'll be able to check more of them off your list. Combine your hotels, flights and rental cars and make big savings.
Can I choose my airline with a Kent County Expedia holiday package?
You can, and with more than 550 airlines to choose from across the globe, it's all about choice. Scroll through the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Kent County holiday package?
Whether it's your flight or hotel, you can cancel or change it. Locked in your Kent County holiday package in the last 24 hours? You may be able to make changes at no cost. For bookings made more than 24 hours ago, you may incur a fee from your hotel, airline or car rental company. For more information, head to our Customer Service Portal. We'll help you each step of the way.

Stay near popular Kent County attractions

Washington College

8.6/10 (87 reviews)
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
See properties

What to do in Kent County

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl

S$47
per adult
Annapolis Ghost Tours Boos & Booze Haunted Pub Crawl
Ashes and Apparitions of Annapolis Ghost Tour

Ashes and Apparitions of Annapolis Ghost Tour

S$41
per adult
100% of travellers recommend
Ashes and Apparitions of Annapolis Ghost Tour
Half Day Private Tour of Annapolis Up to 12 people

Colonial Annapolis and Naval Academy Half Day Private Bus Tour

S$2,235
per traveller
Colonial Annapolis and Naval Academy Half Day Private Bus Tour
See all activities in Kent County

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.