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.
Landing Modern Studio, Gym

Landing Modern Studio, Gym

3 out of 5
South End
Price was $1,855, price is now $1,328 per person
$1,328
per person
Dec 25 - Dec 30
found 23 hours ago
Roundtrip flight included
New York (NYC) to Charlotte (CLT)
This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. A gym and a virtual front desk are also provided.
Dock, Hot Tub & Kayaks on Lake Norman Lakeside Gem by Avantstay

Dock, Hot Tub & Kayaks on Lake Norman Lakeside Gem by Avantstay

3 out of 5
Westport
Price was $3,151, price is now $2,256 per person
$2,256
per person
Dec 25 - Dec 30
found 23 hours ago
Roundtrip flight included
New York (NYC) 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. A terrace is also provided.
Luxury Lakefront Stay Private Dock, Indoor/outdoor Pool The Retreat

Luxury Lakefront Stay Private Dock, Indoor/outdoor Pool The Retreat

3 out of 5
Price was $3,917, price is now $2,869 per person
$2,869
per person
Dec 25 - Dec 30
found 23 hours ago
Roundtrip flight included
New York (NYC) 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 and a terrace are also provided.
Shoreway Cove by Avantstay Waterfront, Pool, Dock

Shoreway Cove by Avantstay Waterfront, Pool, Dock

3 out of 5
Price was $4,598, price is now $3,377 per person
$3,377
per person
Dec 25 - Dec 30
found 23 hours ago
Roundtrip flight included
New York (NYC) to Charlotte (CLT)
This cottage doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and barbecue grills are also provided.
Montclair Manor by Avantstay Lakefront Retreat Dock + Hot Tub + Firepit + Game Room

Montclair Manor by Avantstay Lakefront Retreat Dock + Hot Tub + Firepit + Game Room

3 out of 5
Price was $3,046, price is now $2,242 per person
$2,242
per person
Dec 25 - Dec 30
found 23 hours ago
Roundtrip flight included
New York (NYC) 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.

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
Nov 16 - Nov 17
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
Reserve now, pay when you stay
$62 nightly
The price is $70 total per night
$70 total
Dec 15 - Dec 16
Total with taxes and fees
An outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A picnic area is also provided.
Pool
Pet friendly
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
Nov 15 - Nov 16
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
Clarion Pointe Rock Hill Near University

Clarion Pointe Rock Hill Near University

2.5 out of 5
1106 N. Anderson Road Rock Hill SC
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $81 total per night
$81 total
Nov 29 - Nov 30
Total with taxes and fees
A gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like continental breakfast and WiFi in public areas. Luggage storage is provided and the front desk is staffed around-the-clock.
Breakfast included
Pet friendly
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
Nov 22 - Nov 23
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 buffet breakfast and free self parking.
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
$114 nightly
The price is $126 total per night
$126 total
Dec 13 - Dec 14
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 $1,328. 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 river with clear water, surrounded by lush greenery and rocks.
A sunrise over a rural landscape with a water tower and scattered houses.
A river with autumn-colored trees and a clear blue sky.