Chester Vacations from $288

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
B Ocean Resort Fort Lauderdale Beach

B Ocean Resort Fort Lauderdale Beach

4 out of 5
East Fort Lauderdale
Save 100% on your flight
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
7.6/10 Good! (2,919 reviews)
My wife and i had a great stay this week.

Reviewed on Jun 28, 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Everything was amazing- The accommodations, the property decor, the staff like Adrian and Chef Luis were very personable and welcoming. Our room was upgraded from partial ocean view to full as we were celebrating our 23rd wedding anniversary, so that was a nice touch. We would definitely book again.

Reviewed on May 31, 2025

Treasure Island - TI Las Vegas Hotel & Casino

Treasure Island - TI Las Vegas Hotel & Casino

4 out of 5
Las Vegas Strip
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8.4/10 Very Good! (28,660 reviews)
The property was ok. The rooms were clean. They didn't have room service after 8pm. Which I thought was weird.

Reviewed on Jun 28, 2025

One Bedroom Balcony 1.5 BTH Palms Place StripSuite

One Bedroom Balcony 1.5 BTH Palms Place StripSuite

4.5 out of 5
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
No reviews
StripSuite Palms Place Hotel/Resort & Casino

StripSuite Palms Place Hotel/Resort & Casino

4.5 out of 5
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
No reviews
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Chester Hotel Deals

Quality Inn & Suites Lufkin
Quality Inn & Suites Lufkin
2.5 out of 5
4306 S 1st St, Lufkin, TX
Fully refundableReserve now, pay when you stay
$51 nightly
The price is $58 total per night from Jul 13 to Jul 14
$58 total
Jul 13 - Jul 14
Total includes taxes and fees
6.8/10 (748 reviews)
"Great"

Reviewed on Jun 19, 2025

Quality Inn & Suites Lufkin
Holiday Inn Express & Suites Lufkin South by IHG
Holiday Inn Express & Suites Lufkin South by IHG
2.5 out of 5
4404 S 1st St, Lufkin, TX
Fully refundable
$106 nightly
The price is $120 total per night from Jul 13 to Jul 14
$120 total
Jul 13 - Jul 14
Total includes taxes and fees
8.6/10 Excellent! (539 reviews)
"Hallways smelled musty, staff ok no info given just sign here"

Reviewed on Jun 24, 2025

Holiday Inn Express & Suites Lufkin South by IHG
Best Western Plus Crown Colony Inn & Suites
Best Western Plus Crown Colony Inn & Suites
2.5 out of 5
3211 S 1st Street, Lufkin, TX
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $130 total per night from Jul 6 to Jul 7
$130 total
Jul 6 - Jul 7
Total includes taxes and fees
9/10 Wonderful! (869 reviews)
"It was nice"

Reviewed on Jun 20, 2025

Best Western Plus Crown Colony Inn & Suites
See all 114 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this top destination from $288 on Expedia. But how much your vacation to Chester costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chester?
You can generally find reduced prices and greater availability in January, July and August. Browse our cheap Chester vacation packages and you could score some great off-season deals.
How many days is enough for Chester?
The ideal length of your Chester vacation depends on what you'd like to see and do. Usually, a few days to a week will give you plenty of time to go to all the top sights and explore some hidden gems along the way.
How to find the best Chester package deals?
Begin your search for a Chester package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Chester package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester escape off to a flying start.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester escape by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
Secure fantastic discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Chester vacation.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Chester break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.