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.
Poolside Paradise by Avantstay Waterfront Home + Pool + Spa Dock + Game Room Near Hiking

Poolside Paradise by Avantstay Waterfront Home + Pool + Spa Dock + Game Room Near Hiking

3 out of 5
Save 100% on your flight
Price was $4,922, price is now $3,630 per person
$3,630
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. Families will appreciate the arcade/game room and barbecue grills. An outdoor pool is also provided.
Lakefront Estate Pool + Hot Tub + Dock + Sauna Oasis at Ballycastle

Lakefront Estate Pool + Hot Tub + Dock + Sauna Oasis at Ballycastle

3 out of 5
Save 100% on your flight
Price was $6,820, price is now $4,995 per person
$4,995
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlotte (CLT)
This cottage features an outdoor pool and a sauna. Guests will appreciate free perks like free self parking and WiFi in public areas.
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 $6,714, price is now $4,931 per person
$4,931
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.
Sunset Shores Resort: The Grand House by Avantstay Lakefront, Spa, Private Dock+beach, Game Room

Sunset Shores Resort: The Grand House by Avantstay Lakefront, Spa, Private Dock+beach, Game Room

3 out of 5
Save 100% on your flight
Price was $8,803, price is now $6,520 per person
$6,520
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. A terrace is also provided.
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 $5,482, price is now $4,066 per person
$4,066
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.

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 8 - Aug 9
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.
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 14 - Aug 15
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.
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
$91 nightly
The price is $101 total per night
$101 total
Aug 17 - Aug 18
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.
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
$55 nightly
The price is $63 total per night
$63 total
Aug 10 - Aug 11
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.
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
$108 nightly
The price is $120 total per night
$120 total
Aug 9 - Aug 10
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.
Holiday Inn Rock Hill by IHG

Holiday Inn Rock Hill by IHG

3 out of 5
503 Galleria Blvd Rock Hill SC
Free Cancellation
$84 nightly
The price is $96 total per night
$96 total
Aug 17 - Aug 18
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
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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.
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Frequently asked questions

How much are vacation packages to Chester?
Your travel dreams can all come true in Chester for only $3,630. 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.