Chester Vacations from $312
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The Latest Chester vacation packages
Price found within the past 48 hours. Click for updated prices.
Westgate Flamingo Bay Resort
Spring Valley
$312
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Las Vegas (LAS)
8.8/10 Excellent! (1,012 reviews)
I really enjoyed myself and gave me a home like environment and feeling they were very clean. Staff was willing to work with me when I had an issue with the people upstairs. Their water were leaking in my room. They took care of it right away that it expeditiously, they didn’t have me wait no time I really enjoyed the service and the amenities and the place. Thank you so much and I will be returning and trying to get a timeshare, this is brought to you through via voice text on Miss Collins, Apple iPhone.
Reviewed on Aug 31, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$9,963
per person
Nov 8 - Nov 14
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
SIRTAJ - Beverly Hills
South of Wilshire
$689
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.2/10 Very Good! (1,006 reviews)
Convenient location, I got a discounted price. I asked and was given a courtesy late checkout time by 30 minutes. Comfortable bed. Fancy toilet with many buttons for washing one's undersides. But it was a really hot day and there was no way to turn off the heated toilet seat. Shower head was good. There are cheaper public parking garages on Beverly Blvd and Wilshire Blvd one block away. Best of all is Chaumont Bakery, only 5 mins. walk away on Beverly Blvd, a great place for brunch. Order the almond croissant and mushroom omelet, they are divine.
Reviewed on Sep 3, 2026
The Rose Premium Suite at MGM Signature
$542
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Las Vegas (LAS)
5/10 (6 reviews)
I felt like the walk from the front entrance was quite the distance and you could only catch ride shares from the front entrance. Discovered this the hard way. This particular room had to be close to the pool and club area as you could hear the music late at night.
Reviewed on Jun 15, 2026
Chester Hotel Deals
Best Western Plus Crown Colony Inn & Suites
3211 S 1st Street Lufkin TX
Fully refundableReserve now, pay when you stay
$123 nightly
$139 total
Sep 13 - Sep 14
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"We were in town for a wedding. The hotel was so convenient to the venue, places to eat and shop, and very quiet to be on a busy road. The breakfast tacos were yummy. One drawback was the yogurt machine was empty when I went to breakfast (about 30 minutes before breakfast was over). And the room darkening ..."
Reviewed on Sep 5, 2026
Quality Inn & Suites Lufkin
4306 S 1st St Lufkin TX
Fully refundable
$64 nightly
$72 total
Oct 4 - Oct 5
Total with taxes and fees
7/10 Good! (920 reviews)
"Clean room"
Reviewed on Sep 3, 2026
Holiday Inn Express & Suites Lufkin South by IHG
4404 S 1st St Lufkin TX
Fully refundable
$108 nightly
$122 total
Sep 13 - Sep 14
Total with taxes and fees
8.8/10 Excellent! (615 reviews)
"Good"
Reviewed on Aug 30, 2026
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 $312 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.
