Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

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

The Westin Charlotte

4 out of 5
Uptown Charlotte
Price was $997, price is now $728 per person
$728
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlotte (CLT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a snack bar/deli, and express check-out are also offered.
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
Price was $6,422, price is now $4,670 per person
$4,670
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlotte (CLT)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. Barbecue grills are provided for your convenience.
New Saltwater Pool + Spa, Views Wilson Hideaway

New Saltwater Pool + Spa, Views Wilson Hideaway

3 out of 5
Save 100% on your flight
Price was $5,496, price is now $4,027 per person
$4,027
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlotte (CLT)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool is also provided.
The Grand on Greenbay-7 Bedrooms Sleeps 20 Modern new Build

The Grand on Greenbay-7 Bedrooms Sleeps 20 Modern new Build

3 out of 5
Save 100% on your flight
Price was $6,167, price is now $4,525 per person
$4,525
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlotte (CLT)
Free WiFi in public areas is available at this cottage. Take advantage of the free self parking.
Charlotte Marriott City Center

Charlotte Marriott City Center

4 out of 5
Uptown Charlotte
Price was $1,009, price is now $744 per person
$744
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlotte (CLT)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, a snack bar/deli, and a grocery/convenience store are also on offer.

Top Chester hotels deals

Motel 6 Richburg, SC

Motel 6 Richburg, SC

2 out of 5
2912 Parkway Blvd Chester SC
Free Cancellation
Reserve now, pay when you stay
$67 nightly
The price is $75 total per night
$75 total
Aug 20 - Aug 21
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli is provided and the front desk is staffed around-the-clock.
Pet friendly
Parking included
Executive Inn Chester

Executive Inn Chester

2.5 out of 5
1632 J A Cochran Bypass Chester SC
Free Cancellation
$69 nightly
The price is $78 total per night
$78 total
Aug 26 - Aug 27
Total with taxes and fees
An outdoor pool is featured at this motel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A picnic area is provided and the front desk is staffed around-the-clock.
Pool
Breakfast included
Inn Upon Moon River Plantation

Inn Upon Moon River Plantation

2.5 out of 5
119 Pinckney Street Chester SC
$153 nightly
The price is $167 total per night
$167 total
Aug 23 - Aug 24
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the laundry service. A restaurant, laundry facilities, and concierge services are also provided.
Breakfast included
Parking included
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
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $96 total per night
$96 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like full breakfast and free self parking.
Pool
Breakfast included
Days Inn by Wyndham Rock Hill

Days Inn by Wyndham Rock Hill

2 out of 5
875 Riverview Rd Rock Hill SC
Free Cancellation
Reserve now, pay when you stay
$54 nightly
The price is $61 total per night
$61 total
Aug 22 - Aug 23
Total with taxes and fees
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. Business travelers can take advantage of the business center. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Breakfast included
Holiday Inn Express & Suites Fort Mill by IHG

Holiday Inn Express & Suites Fort Mill by IHG

2.5 out of 5
1655 Carolina Place Drive Fort Mill SC
Free Cancellation
$113 nightly
The price is $125 total per night
$125 total
Aug 23 - Aug 24
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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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.

Stay near popular Chester attractions

Chester State Park

8.0/10 (2 reviews)
You can take time to visit Chester State Park during your travels to Chester. Experience the area's jazz scene and live music.
See properties

Frequently asked questions

How much are vacation packages to Chester?
Your travel dreams can all come true in Chester for only $728. Our vacation packages include flights and hotels, so organizing your itinerary will be a breeze. The only thing you'll need to concentrate on is having an incredible time.
How long should my Chester vacation be?
Many travelers pack their bags and vacation in Chester for an average of 3 nights. That gives you a rough guide, but don't let it restrict you. Whether you stay for a few days to see the main sights or hang around to explore new places, an unforgettable adventure awaits.
Where can I get the best vacation package deals for Chester?
With at least 400 airline partners and 1,000,000 hotels across the world, it's hard to top Travelocity. Browse our comprehensive range and score an incredible Chester package deal. Don't you love it when traveling is that easy?
Why should I purchase my Chester vacation bundle via Travelocity?
Because you'll never wander on your own if you lock in your vacation through us, and we offer 24/7 customer support and exceptional service to boot. Add to that our Price Match Guarantee and countless destinations to choose from. It's our job to make your vacation as unforgettable as possible.
Will I save money on my Chester car rental if I book it with my hotel or flight?
Sure can — bundle your hotel, car and flight into a Chester vacation package and you can save a handsome sum. With so much to discover in the Chester area, having your own ride will make it easy to explore. Once you've buckled yourself in, get out on the wide open road and make tracks to Biltmore Estate, an unmissable sight about 95 mi from Chester.
Which airport is best for Chester?
Charlotte-Douglas Intl. Airport (CLT) (40 mi away from downtown), Greenville-Spartanburg Intl. Airport (GSP) (60 mi away from central Chester) and Columbia Metropolitan Airport (CAE) (55 mi away from central Chester) are the main hubs in Chester.
What is there to do in Chester?
While taking the path less traveled is no doubt rewarding, you shouldn't miss the big attractions that make a destination famous. Chester State Park and Chester County Historical Society Museum and Archives are just two of them in Chester.
Where should I stay when visiting Chester?
Many travelers choose to check in to the Inn Upon Moon River Plantation. It's a great base for your Chester escape.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A sunrise over a rural landscape with a water tower and scattered houses.
A river with autumn-colored trees and a clear blue sky.