Chester Vacation Packages
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Top Chester vacation deals
Price found within the past 48 hours. Click for updated prices.
- Wyndham Grand Pittsburgh Downtown
Sept 17 - Sept 20Wyndham Grand Pittsburgh Downtown + Flight
Downtown Pittsburgh3 nights3.5 star property8.2/10 - Very good (3,633 reviews)"The musty smell was terrible. Why we even had a phone in our room is beyond me since it wasn't even plugged in nor was there even a cord which im pretty sure would be a fire hazard or even a medical hazard. the floors were disgusting dirty. the bed sheet was just a bed sheet wasn't even a fitted sheet even they smelled musty. Would probably never stay again."Reviewed July 17, 2026Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)YHZ - PIT • 1 stop PIT - YHZ • 1 stopCA $1,154CA $826found 2 hours agoper traveller - Stay Pittsburgh
Sept 17 - Sept 20Stay Pittsburgh + Flight
Downtown Pittsburgh3 nights2.0 star property8.0/10 - Very good (307 reviews)"Affordable"Reviewed July 4, 2026Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)YHZ - PIT • 1 stop PIT - YHZ • 1 stopCA $1,413CA $1,066found 2 hours agoper traveller - Joinery Hotel Pittsburgh, Curio Collection by Hilton
Sept 2 - Sept 7Joinery Hotel Pittsburgh, Curio Collection by Hilton + Flight
Downtown Pittsburgh5 nights4.0 star property8.6/10 - Excellent (1,575 reviews)Roundtrip • Québec City (YQB) - Pittsburgh (PIT)YQB - PIT • 1 stop PIT - YQB • 1 stopCA $1,564CA $1,242found 0 hours agoper traveller - Crowne Plaza Suites Pittsburgh South by IHG
Sept 11 - Sept 14Crowne Plaza Suites Pittsburgh South by IHG + Flight
Bethel Park3 nights3.5 star property8.6/10 - Excellent (1,003 reviews)Roundtrip • Toronto (YYZ) - Pittsburgh (PIT)YYZ - PIT • 1 stop PIT - YYZ • 1 stopCA $1,509CA $1,218found 1 day agoper traveller - DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown
Sept 10 - Sept 14DoubleTree by Hilton Hotel & Suites Pittsburgh Downtown + Flight
Downtown Pittsburgh4 nights4.0 star property8.4/10 - Very good (1,092 reviews)Roundtrip • Halifax (YHZ) - Pittsburgh (PIT)YHZ - PIT • 1 stop PIT - YHZ • 1 stopCA $1,792CA $1,509found 1 day agoper traveller
Chester Hotel Deals
8.6 out of 10, Excellent, (792 reviews)
8.6/10
Excellent
(792 reviews)
"Breakfast was nice"
The price is CA $140
CA $140
CA $157 total
includes taxes & fees
Aug 16 - Aug 17
8.0 out of 10, Very good, (1,002 reviews)
8.0/10
Very good
(1,002 reviews)
"Me and my daughters stayed in room 2094 last night. I booked a room online and when we got there, we had to carry all of our bags up two flights of stairs which was not really a problem. But I had talked to the guy that was working at the front desk/ check- in twice about the room and the condition of it. That room had bedbugs and blood slots from them on the corners of the sheets and in the lampshade. We felt them last night and the air conditioner wasn’t working until about 4 AM when it kicked...
The price is CA $150
CA $150
CA $195 total
includes taxes & fees
Jul 19 - Jul 20
Quality Inn East Liverpool - Calcutta
Quality Inn East Liverpool - Calcutta2.5 star property
6.6 km from Chester
7.8 out of 10, Good, (496 reviews)
7.8/10
Good
(496 reviews)
"We went down to breakfast at 9:10 and there was no waffle batter and only some yogurt in the fridge for breakfast.
"
The price is CA $149
CA $149
CA $169 total
includes taxes & fees
Aug 11 - Aug 12
Microtel Inn & Suites By Wyndham Beaver Falls
Microtel Inn & Suites By Wyndham Beaver Falls2.5 star property
23.4 km from Chester
9.0 out of 10, Wonderful, (1,006 reviews)
9.0/10
Wonderful
(1,006 reviews)
"Realmente todo limpio, sin embargo un desayuno pobre."
The price is CA $120
CA $120
CA $133 total
includes taxes & fees
Jul 21 - Jul 22
Postcard Cabins Beaver Creek Ohio, Outdoor Collection by Marriott Bonvoy
Postcard Cabins Beaver Creek Ohio, Outdoor Collection by Marriott Bonvoy2.5 star property
16 km from Chester
9.4 out of 10, Exceptional, (44 reviews)
9.4/10
Exceptional
(44 reviews)
"The cabin was so cute and quaint. The amenities they provided was such a bonus- firewood bundles, fire starter, fire poker, snacks, water, kitchen amenities and so much more! The staff was very communicative and helpful! It was a great couples getaway!"
The price is CA $142
CA $142
CA $279 total
includes taxes & fees
Aug 16 - Aug 17
8.4 out of 10, Very good, (721 reviews)
8.4/10
Very good
(721 reviews)
"good location"
The price is CA $154
CA $154
CA $174 total
includes taxes & fees
Aug 5 - Aug 6
7.6 out of 10, Good, (566 reviews)
7.6/10
Good
(566 reviews)
The price is CA $81
CA $81
CA $91 total
includes taxes & fees
Aug 2 - Aug 3
Hilton Garden Inn Pittsburgh Area Beaver Valley, PA
Hilton Garden Inn Pittsburgh Area Beaver Valley, PA3.0 star property
21.6 km from Chester
9.2 out of 10, Wonderful, (511 reviews)
9.2/10
Wonderful
(511 reviews)
"Fresh; clean; beautiful facilities; good price"
The price is CA $145
CA $145
CA $161 total
includes taxes & fees
Jul 29 - Jul 30
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.
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 Chester vacation package cost?
You can grab a vacation package to this top destination from CA $826 on Expedia. But how much your vacation to Chester costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Chester?
The off-season is the best time to travel to Chester if you're on a budget. Another tip for getting cheap Chester vacation packages? Avoid visiting during public holidays and any major events or festivals.
How many days is enough for Chester?
The ideal duration for your Chester vacation depends on what you'd like to see. Generally, a handful of days to a week will give you time to tick off all the main attractions and discover some hidden spots along the way.
How to find the best Chester package deals?
Use Expedia's filters to help you find some of the best 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 trip for midweek, or search for Chester package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Chester vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component separately. And you'll still get the freedom to create a customized Chester vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Chester?
If you're planning a spur-of-the-moment Chester getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Chester?
- Choose your travel dates: The things you'd like to do in Chester and your favourite season will help you decide when to go.
- Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Chester.
- Decide how long to go for: Now that you're up to speed on Chester, you can figure out the ideal length of your break. Create a draft itinerary and give yourself enough time to cover everything you want to see.
- Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the right Chester vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.