Chester Vacations from $485

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
The Local House

The Local House

3.5 out of 5
South Beach
Price was $1,022, price is now $485 per person
$485
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,001 reviews)
We had another great stay at the Local House. We will be returning soon!

Reviewed on Nov 15, 2025

Hawks Cay Resort

Hawks Cay Resort

4 out of 5
Price was $1,754, price is now $775 per person
$775
per person
Jan 22 - Jan 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,003 reviews)
Everything in this island is perfect and amazing.

Reviewed on Dec 5, 2025

Iberostar Waves Miami Beach

Iberostar Waves Miami Beach

4 out of 5
South Beach
Price was $1,104, price is now $509 per person
$509
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (825 reviews)
Great property access to two sunbeds included on the beach!

Reviewed on Nov 25, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was $12,979, price is now $6,177 per person
$6,177
per person
Feb 25 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1 review)
Iberostar Waves Berkeley Shore

Iberostar Waves Berkeley Shore

4 out of 5
South Beach
Price was $1,076, price is now $513 per person
$513
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.8/10 Excellent! (1,449 reviews)
I decided to stay here for my birthday and I loved it. The rooms very clean, I had a complimentary wine although I don't drink, I appreciated it nonetheless. I absolutely LOVED the breakfast, every day I chose something new and everything tasted good. I have since recommended this hotel to a friend who is visiting Miami soon, and he already confirmed his booking. Oh, let me also say that all members of staff were very welcoming, courteous and very helpful. I HIGHLY recommend and it's in a great spot too.

Reviewed on Dec 4, 2025

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Chester Hotel Deals

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
$108 nightly
The price is $122 total per night from Dec 31 to Jan 1
$122 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
9/10 Wonderful! (919 reviews)
a nice, spacious room

Reviewed on Nov 27, 2025

Best Western Plus Crown Colony Inn & Suites
Hampton Inn & Suites Lufkin, TX

Hampton Inn & Suites Lufkin, TX

2.5 out of 5
4400 South First Street Lufkin TX
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $117 total per night from Dec 14 to Dec 15
$117 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (612 reviews)
The room and whole hotel were clean.

Reviewed on Dec 2, 2025

Hampton Inn & Suites Lufkin, TX
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 $57 total per night from Jan 4 to Jan 5
$57 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
6.8/10 (812 reviews)
The room was clean

Reviewed on Nov 17, 2025

Quality Inn & Suites Lufkin
See all 116 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 $485 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.