Chester Vacations from $554

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Aliante Casino & Hotel

Aliante Casino & Hotel

4 out of 5
Aliante Sun City
Save 100% on your flight
Price was $1,121, price is now $554 per person
$554
per person
Apr 25 - May 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Las Vegas (LAS)
8.8/10 Excellent! (1,500 reviews)
All of it …outstanding!

Reviewed on Feb 4, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,482, price is now $687 per person
$687
per person
Apr 22 - Apr 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

4.5 out of 5
Hollywood
Price was $2,714, price is now $1,272 per person
$1,272
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Los Angeles (LAX)
9.2/10 Wonderful! (80 reviews)
We loved our stay here! Having an apartment was home away from home. Quiet neighborhood, close to everything. Comfy beds are hard to find and i was very pleased. Host was quick to respond.

Reviewed on Jan 23, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was $1,244, price is now $590 per person
$590
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

Ilios Rentals

Ilios Rentals

2 out of 5
Downtown Miami
Price was $2,042, price is now $1,035 per person
$1,035
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
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
$59 nightly
The price is $67 total per night from Feb 22 to Feb 23
$67 total
Feb 22 - Feb 23
Total with taxes and fees
6.8/10 (833 reviews)
Nice lady at the desk

Reviewed on Dec 26, 2025

Quality Inn & Suites Lufkin
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
$127 nightly
The price is $144 total per night from Feb 15 to Feb 16
$144 total
Feb 15 - Feb 16
Total with taxes and fees
9/10 Wonderful! (952 reviews)
The staff was amazing!! Check in was quick and easy. The room was clean, smelled fresh, and well stocked.

Reviewed on Jan 23, 2026

Best Western Plus Crown Colony Inn & Suites
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
$105 nightly
The price is $119 total per night from Feb 15 to Feb 16
$119 total
Feb 15 - Feb 16
Total with taxes and fees
8.8/10 Excellent! (574 reviews)
Hotel staff was polite and efficient. Room was clean and comfortable.

Reviewed on Jan 30, 2026

Holiday Inn Express & Suites Lufkin South by IHG
See all 119 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 $554 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.