Chester Vacations from $271

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Your Chester Vacation

Book a customized Chester vacation package that has everything you need and no unnecessary extras. Good for cycling, views and nature, consider basing yourself in the neighborhood of Kent Narrows. Make your trip to Chester even more exciting by going sightseeing. Chesapeake Bay Environmental Center, Matapeake State Park and Love Point State Park are among the leading attractions worth exploring. Whatever your travel plans or the size of your budget, putting together a tailored Chester vacation is a breeze with Expedia.

The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
The breakfast was awesome! Lots of choices hot and cold alike: pleasantly surprised with the height of the showerhead and the water pressure. The only reason I did not get five stars is because it’s valet parking. For there’s no parking on site.( again downtown so maybe this is not surprising) There is a parking garage down the street.

Reviewed on Jun 16, 2024

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Aug 22 - Aug 25
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,013 reviews)
Hotel is fine. Staff is excellent. No real restaurant yet. Only complaint is trying to break big bills to give out tips to staff is difficult to impossible. Usually, there is no cash at the front desk. The staff suffers because of this.

Reviewed on Jun 15, 2024

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 22 - Aug 25
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,003 reviews)
The Hotel in s within walking distance of the capitol and the mall. The staff was amazingly kind and every restaurant we tried served delicious food. Our room was small and cozy. The view was of an apartment complex behind the hotel and part of the hotels roof where the unit was stored. We didn’t mind the view because it was like watching DC living without all the amenities which made it a great experience.

Reviewed on Jun 17, 2024

Ulysses

Ulysses

3 out of 5
Midtown
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (385 reviews)
Very charming hotel with a very friendly and helpful staff oh just had a nice vibe.

Reviewed on Jun 8, 2024

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (909 reviews)
Amazing property, staff was spectacular. The pool was a huge highlight- thanks Oliver for being such an awesome waiter!

Reviewed on Jun 16, 2024

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
4,200
Top Sights
Sandy Point State Park, Sandy Point Beach and Matapeake State Park

Chester Hotel Deals

Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is $152 per night from Jul 1 to Jul 2
$152
$196 total
includes taxes & fees
Jul 1 - Jul 2
8.8/10 Excellent! (1,628 reviews)
"Liked the history. close to everything!"

Reviewed on Jun 15, 2024

Historic Inns of Annapolis
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
The price is $178 per night from Jul 1 to Jul 2
$178
$203 total
includes taxes & fees
Jul 1 - Jul 2
9.2/10 Wonderful! (1,033 reviews)
"We had a nice time for our baby moon!"

Reviewed on Jun 14, 2024

Graduate Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is $100 per night from Jul 1 to Jul 2
$100
$114 total
includes taxes & fees
Jul 1 - Jul 2
8.8/10 Excellent! (1,006 reviews)
Finally, a nice place
"Stopped here after a week of touring Philadelphia, New Jersey, and Delaware. Nice hotel, well maintained, quiet, and located in a good area. Breakfast was very nice with a good selection of items that did not contain pork (thank you). Pool was closed but that had no impact on us. We will not hesitate ..."

Reviewed on Jun 16, 2024

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,182 properties in Chester
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Get your credit card ready, because a trip to Chester starts from a tempting $271. When you combine your flights, hotels and more into a vacation package, you’ll pick up the biggest deals.
How do I get a cheap travel package to Chester?
By bundling. Hotels, flights and rental cars — combine whatever you need into a Chester vacation package to save a ton of cash. Score even better deals when you add extras such as activities or tours to your booking. But that’s not the only impressive part. You have the freedom to tailor your trip your way. We offer more than 550 air carriers and 1,000,000 properties all over the world, so that everyone has a chance to travel and live out those vacation fantasies.
What are the top hotels in Chester?
When it comes to comfy places to stay in Chester, you can’t go past Bentons Pleasure - Cox Creek, Pier And Sunsets. Have a look at our offers and pick up a great price.
How far in advance should I book my Chester vacation?
Reserving your seat early with Expedia means one less thing to worry about. Many air carriers advertise prices up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Chester are still known to appear in the weeks leading up to departure.
What does an Expedia Chester travel package include?
Flights, hotels and car rentals — we connect you to the very best bargains. All you have to do is decide on your preferred combination. Once you’ve made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to create an amazing Chester trip.
What should I know before booking a Chester travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and enjoy terrific discounts. Hotels aren’t your only option, though. We have beach villas, mountain cabins and even treehouses and ranches!
Can I choose my airline with a Chester Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Chester vacation package?
Don’t stress if you’re rethinking your Chester vacation package — it’s possible to change or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally get that life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you’re ready to make changes, we’ll take care of it.

Discover the most popular places to visit in Chester

Image for Chesapeake Exploration Center

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

Chesapeake Exploration Center

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.