Chester Vacation Packages

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Your Chester Vacation

Reserve a Chester vacation package and get set to experience the best of this city. Consider basing yourself in the neighborhood of Kent Narrows, which is good for cycling, views and nature. If your trip to Chester includes some sightseeing, check out renowned attractions like Chesapeake Bay Environmental Center, Eastern Neck National Wildlife Refuge and Love Point State Park. Stop daydreaming and start doing. Browse the multitude of options on Expedia today and finally put your Chester vacation plans into gear!

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Northwest
per person
Jun. 28 - Jul. 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.6/10 Excellent! (1,094 reviews)
Love the room! Spacious and comfortable! Neighborhood is walkable and near public transportation

Reviewed on May 1, 2025

Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Jun. 28 - Jul. 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.2/10 Very Good! (601 reviews)
Nobody said that parking is not free.

Reviewed on Apr. 30, 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
per person
Jun. 28 - Jul. 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,419 reviews)
I am extremely satisfied with the Lyle. It's in a beautiful section of DC. Very walkable to many locations. The hotel itself is very lovely - the common area and the room. The staff is extremely customer service oriented - and are very pleasant. The bar and restaurant are VERY good in terms of taste, quality and style. There is no reason to stay anywhere else. I would stay here again.

Reviewed on May 1, 2025

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Jun. 28 - Jul. 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (2,353 reviews)
Front desk personnel were very nice and helpful

Reviewed on Apr. 30, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Jun. 28 - Jul. 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.6/10 Excellent! (1,007 reviews)
Everything was great. Easy to access and navigate to many different activities. Just not a super quick response from staff when requesting towels

Reviewed on Apr. 27, 2025

Ready to book your vacation to Chester?

 

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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 CA $223 per night from May 8 to May 9
CA $223
CA $302 total
includes taxes & fees
May 8 - May 9
8.8/10 Excellent! (1,757 reviews)
"We had an undesirable use of the shower. It was extremely small and without a reomoveable showerhead therefore making it impossible to bathe and rinse. At the least if there was a removeable wand/shower handle it would allow for a short person to have the spray hit more than just the top of their ..."

Reviewed on Apr. 29, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis
Graduate by Hilton Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from May 26 to May 27
CA $234
CA $267 total
includes taxes & fees
May 26 - May 27
9.4/10 Exceptional! (1,001 reviews)
Service and accommodation top notch!
"Second time staying here. Hotel is beautiful. This time we were staying for 2 nights and the first night, the room smelled of mold or mildew as soon as I opened the door. Not sure what was going on, but I called the front desk in the am. They happily accommodated our request to be moved. We were ..."

Reviewed on Apr. 29, 2025

Graduate by Hilton 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 CA $134 per night from May 8 to May 9
CA $134
CA $153 total
includes taxes & fees
May 8 - May 9
8.8/10 Excellent! (1,002 reviews)
"Wonderful staff!"

Reviewed on Apr. 29, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,243 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from CA $673 on Expedia, you’ll be pleasantly surprised at how much a vacation to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
Travel in the off-peak season and you’re likely to score cheap Chester vacation packages. Keep in mind that school vacation periods and local festivals and events can impact prices, so do a little research before you go.
How many days is enough for Chester?
When planning your Chester vacation, a handful of days will be enough to see all the highlights. Be sure to stop by Eastern Neck National Wildlife Refuge — it’s one of the major attractions in this destination. If you want more adventure, consider basing yourself here and setting off on some tours from Chester.
How to find the best Chester package deals?
Use Expedia’s handy filters to help you find some terrific Chester package deals. When you start your search, just set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your adventure for midweek, or search for Chester package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it’s typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation package. Check the “Package” heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
If you’ve got your Chester vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Chester?

  1. Choose your dates: What you plan to do in Chester and your favourite season will help you decide when to go.
  2. Plan your budget wisely: Besides the cost of your accommodations, you’ll need to factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Chester.
  3. Determine how many days away: Start by compiling a list of the sights and activities you’d like to experience in Chester. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that’s left now is to choose a Chester vacation package that brings all your bookings together.

Discover the most popular places to visit in Chester

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