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.
Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
Aug 7 - Aug 10
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.2/10 Wonderful! (621 reviews)
Great location, great restaurants although the bar was really noisy on the rooftop. The elevators were really slow and at times, felt like only one of four was ever working. The TV in the room kept going in and out. Otherwise we enjoyed our stay!

Reviewed on Jun. 28, 2025

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Save 100% on your flight
per person
Jul 30 - Aug 2
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.2/10 Wonderful! (184 reviews)
Everything was exceptional as usual. Staff knew our names, CUT was excellent. Downside is the pool needed cleaning/chemicals and the heater was broken. The pool is a major selling point for us so it was a bit of a let down. We will be back again but will check on the status of the pool first. Staff is excellent, always have gifts for the kids and delicious baked goods in our room. Highly recommend for families.

Reviewed on Jun. 10, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Aug 8 - Aug 11
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,005 reviews)
The updates and upgrades are beautiful. My favorite place to stay in Washington DC

Reviewed on Jun. 27, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
per person
Aug 7 - Aug 10
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
10/10 Exceptional! (2 reviews)
I really enjoyed my stay here. The bed is comfy, the water pressure in the shower is amazing, the location is right by the red line, the onsite restaurant is really nice. Generally it’s a very luxurious

Reviewed on Jun. 27, 2025

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Aug 18 - Aug 23
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.8/10 Exceptional! (944 reviews)
We try to stay at different properties each time we’re in DC. We’ll be hard-pressed to find one that is better than the Jefferson. The rooms sparkled, the staff were incredibly helpful, the amenities were spot-on, and the location was great.

Reviewed on May 26, 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
8.8/10 Excellent! (1,778 reviews)
"Super easy check in. Valet service was awesome as well."

Reviewed on Jun. 25, 2025

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Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jul 21 to Jul 22
CA $140
CA $160 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"It was very nice and comfortable"

Reviewed on Jun. 22, 2025

Hilton Garden Inn Annapolis Downtown
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 $138 per night from Jul 13 to Jul 14
CA $138
CA $157 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Loved my stay! There were some water stains on top of the room which I would guess is just cons of Maryland weather since I was on the top floor. But the breakfast was great, which is hard to find after Covid and the staff were so friendly and accommodating. Also the room itself was a classic style ..."

Reviewed on Jun. 23, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,238 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 $644 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.