Chester Vacations from $421

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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.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Charlotte Marriott City Center
Hilton Charlotte University Place
The Westin Charlotte
Omni Charlotte Hotel
Grand Bohemian Charlotte, Autograph Collection
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Discover the most popular places to visit in Chester

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
$72 nightly
The price is $81 total per night from Aug 24 to Aug 25
$81 total
Aug 24 - Aug 25
Total with taxes and fees
6.6/10 (322 reviews)
"The breakfast was gross and we had to change rooms to an upstairs one because the toilet was broken in the first one."

Reviewed on Aug 20, 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
$142 nightly
The price is $155 total per night from Aug 25 to Aug 26
$155 total
Aug 25 - Aug 26
Total with taxes and fees
9/10 Wonderful! (44 reviews)
Southern Charm & Hospitality
"I thoroughly enjoyed my stay! The House is beautiful and filled with memorabilia of great artists from the jazz and blues fields. The area is very quiet and picturesque. I look forward to my next trip up to the Chester, SC area. I highly recommend this Bed and Breakfast!"

Reviewed on Jul 24, 2025

Inn Upon Moon River Plantation
Clarion Pointe Near University

Clarion Pointe Near University

2.5 out of 5
1106 N. Anderson Road, Rock Hill, SC
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $78 total per night from Aug 31 to Sep 1
$78 total
Aug 31 - Sep 1
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Very convenient location just off I77."

Reviewed on Aug 20, 2025

Clarion Pointe Near University
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.

Things to do near Chester

Chester, South Carolina, offers a delightful escape for outdoor enthusiasts and couples seeking romance. With its scenic recreational areas, an amusement park, and a welcoming resort, visitors can enjoy excellent adventures and outdoor fun. Whether you're looking for exciting outdoor games or more adventurous activities, Chester provides a perfect backdrop for relaxation and adventure alike.

Shopping

In Chester, you can enjoy local shopping experiences. If you're up for a drive, the Rock Hill Galleria offers a variety of stores 22 miles away. For unique finds, check out FLASHES FIREWORKS, LLC, located 19 miles from Chester, or visit the Lancer Center, 24 miles away.

Recreation

The Rock Hill Sports & Event Center, located 19 miles from Chester, offers a vibrant atmosphere for sports enthusiasts. At Pinetuck Golf Club, 15 miles away, enjoy outdoor golfing amidst scenic views. For entertainment, the Old Town Amphitheater, also 19 miles from Chester, hosts lively music concerts.

Adventure

The Piedmont Medical Center Trailhead, 24 miles from Chester, offers invigorating trails perfect for hiking and biking amidst nature's beauty. Lancaster Super Speedway, 25 miles away, is ideal for adrenaline junkies looking for thrilling motor racing experiences. For family fun, the Slot Car Cave, 23 miles from Chester, features exciting arcade activities.

Nightlife

In Chester, South Carolina, enjoy a laid-back nightlife with local bars and live music venues. Visit spots like The Cotton Mill and Chester's own pubs for a friendly atmosphere. Experience karaoke nights and dance events, all while soaking in the charm of this small-town community.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Chester

Chester, South Carolina, offers a delightful mix of outdoor beauty and rich history, making it perfect for romantic getaways and family adventures. Explore local attractions such as modern and historic colleges, as well as engaging museums that provide cultural experiences. Whether you're seeking scenic views or educational outings, Chester has something for every traveler looking to enjoy its charm and character.

  • Chester County Transportation Museum: Discover the rich transportation history of Chester County at this engaging museum. Explore fascinating exhibits showcasing vintage vehicles, local artifacts, and the evolution of transportation in the area, all set in a culturally vibrant atmosphere.
  • Historic Brattonsville: Step back in time at Historic Brattonsville, an 18th-century living history site located 11 miles from Chester. Experience reenactments, guided tours, and preserved buildings that illustrate the daily lives of early settlers in a culturally rich setting.
  • Olde English District: Enjoy family-friendly outdoor activities in the Olde English District, a scenic area within Chester. Explore parks, hiking trails, and local events that celebrate the region's natural beauty and community spirit.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January43.2°F (6.2°C)Light RainMostly SunnyAverageSlightly Low
February47.1°F (8.4°C)Light RainMostly SunnyAverageAverage
March53.4°F (11.9°C)Light RainMostly SunnySlightly HighAverage
April61.7°F (16.5°C)Light RainMostly SunnyAverageAverage
May69.8°F (21.0°C)Light RainMostly SunnyAverageSlightly High
June77.2°F (25.1°C)Light RainMostly SunnyAverageSlightly High
July80.4°F (26.9°C)Light RainMostly SunnySlightly HighSlightly High
August78.6°F (25.9°C)Light RainMostly SunnyAverageAverage
September73.6°F (23.1°C)Light RainMostly SunnySlightly HighAverage
October63.3°F (17.4°C)Light RainMostly SunnySlightly LowAverage
November52.5°F (11.4°C)Light RainMostly SunnySlightly LowSlightly Low
December47.1°F (8.4°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Chester

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chester.
  • Consider traveling during the off-peak season (typically November to January) for more affordable package holidays to Chester.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this destination from $421 on Expedia. However, how much your vacation to Chester costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chester?
You can usually find reduced prices and better availability in January, September and November. Take a look at our cheap Chester vacation packages and you could get some great off-season discounts.
How many days is enough for Chester?
The ideal duration for your Chester vacation depends on what you'd like to do and see. Typically, a few days to a week will give you plenty of time to tick off all the leading attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Chester?
It's no wonder a Chester vacation is on the to-do list of many travelers. Popular attractions like Chester State Park are just the beginning of things to see and do here.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Chester package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
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 flight, hotel and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a personalized Chester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Chester?
Enjoy incredible bargains by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester trip.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Your Chester trip is meant to be a relaxing escape from your busy life, not a source of money worries. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.