Chester Vacation Packages

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Your Chester Vacation

With a vacation package to Chester, say goodbye to travel planning and hello to hassle-free adventure. Every detail of your getaway has been taken care of before you go, so you can get on with experiencing this exciting city. Fill your itinerary with visits to Chester State Park, Mountain Lakes and Chester County Historical Society Museum and Archives, some of the attractions you really should see during a trip to Chester. Expedia will help you escape your daily routine. Tailor your vacation to Chester to match your travel style, whatever that may look like.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Westin Charlotte

The Westin Charlotte

4 out of 5
Uptown Charlotte
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Charlotte (CLT)
8.8/10 Excellent! (1,015 reviews)
Very nice property. Clean and spacious rooms with large showers.

Reviewed on Jul. 2, 2025

Oasis at Ballycastle by Avantstay Private Beach

Oasis at Ballycastle by Avantstay Private Beach

3 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 8
found 23 hours ago
Roundtrip flight included
Edmonton (YEG) to Charlotte (CLT)
No reviews
Family Lake House Retreat by Avantstay Sleeps 28

Family Lake House Retreat by Avantstay Sleeps 28

3 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 8
found 23 hours ago
Roundtrip flight included
Edmonton (YEG) to Charlotte (CLT)
No reviews

Hideaway Cove Private Dock, Firepit, New Build

3 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 8
found 23 hours ago
Roundtrip flight included
Edmonton (YEG) to Charlotte (CLT)
No reviews
Stay Awhile by Avantstay Lakefront + Pool, Dock

Stay Awhile by Avantstay Lakefront + Pool, Dock

3 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 8
found 23 hours ago
Roundtrip flight included
Edmonton (YEG) to Charlotte (CLT)
No reviews

Ready to book your vacation to Chester?

 

Choose your dates

Chester Hotel Deals

Motel 6 Richburg, SC
Motel 6 Richburg, SC
2 out of 5
2912 Parkway Blvd, Chester, SC
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from Jul 7 to Jul 8
CA $98
CA $110 total
Jul 7 - Jul 8
includes taxes & fees
6.6/10 (310 reviews)
"Na"

Reviewed on May 29, 2025

Motel 6 Richburg, SC
Inn Upon Moon River Plantation
Inn Upon Moon River Plantation
2.5 out of 5
119 Pinckney Street, Chester, SC
The price is CA $193 per night from Jul 7 to Jul 8
CA $193
CA $210 total
Jul 7 - Jul 8
includes taxes & fees
9/10 Wonderful! (43 reviews)
"Wonderful hosts"

Reviewed on Apr. 28, 2025

Inn Upon Moon River Plantation
La Quinta Inn & Suites by Wyndham Rock Hill
La Quinta Inn & Suites by Wyndham Rock Hill
3 out of 5
1235 Springdale Rd, Rock Hill, SC
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Jul 13 to Jul 14
CA $133
CA $148 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (1,059 reviews)
La Quinta in Rock Hill
"Check in was quick and easy and we were given some local recommendations which was really appreciated. Our room was spacious and clean and the bed was super comfortable. Also used the fitness room and it was well equipped and everything worked well."

Reviewed on Jun. 27, 2025

La Quinta Inn & Suites by Wyndham Rock Hill
See all 253 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?
You can snap up a vacation package to this top destination from CA $1,179 on Expedia. But how much your vacation to Chester costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Chester?
If you'd like to book a cheap Chester vacation package, consider travelling in September, October and December. You'll typically find lower prices on flights and hotels during these months --- ideal for a budget-friendly break.
How many days is enough for Chester?
Typically, a handful of days is enough to check out the major attractions during your Chester vacation. But if you want to have more time to kick back or take day tours, think about extending your trip.
Is it worth booking a vacation package to Chester?
It's no wonder a Chester vacation is on the to-do list of many travellers. Well-known attractions like Chester State Park are just the beginning of things to keep you busy here.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Chester package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can customize your Chester trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Chester?
If you're planning a spur-of-the-moment Chester vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Chester?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Chester.
  2. Calculate your budget: Make sure you have enough money to cover everything from dining out and transportation to experiences and flights. Your accommodations will probably be the largest expense during your trip to Chester.
  3. Decide how long to go for: Now that you know more about Chester, you can figure out the right length of your break. Put together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chester vacation package.

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