Chester Vacations from $753

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The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Teton Peaks Resort

Teton Peaks Resort

2.5 out of 5
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Idaho Falls (IDA)
8.6/10 Excellent! (414 reviews)
Great place to stay. Very clean, comfortable beds. The front desk guy was very polite and kind. We love their coffee place. Highly recommend this place!

Reviewed on May 25, 2025

Sawtelle Mountain Resort

Sawtelle Mountain Resort

2.5 out of 5
per person
Aug 25 - Aug 29
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Idaho Falls (IDA)
9.2/10 Wonderful! (1,007 reviews)
The Hotel is a unknown treasure. If it was in west yellowstone it would draw $600 a night. The drive is a easy one to yellowstone west entrance 20-30 minutes. The grounds are superb, great staff, good breakfasts. Rooms were very clean and are was very nice. If you want an adventure, drive up Sawtelle mountain,,,,,

Reviewed on Jun 19, 2025

Timbers at Island Park Village Resort

Timbers at Island Park Village Resort

3 out of 5
per person
Aug 25 - Aug 29
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Idaho Falls (IDA)
8.8/10 Excellent! (374 reviews)
Good location. Quiet. Nice size and price comparable to a hotel!

Reviewed on Jun 10, 2025

The Hideaway Lodge

The Hideaway Lodge

3.5 out of 5
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Idaho Falls (IDA)
8.8/10 Excellent! (282 reviews)
Nice place unless you have a room under the kitchen area...You won't be able to sleep after 6 am Steps from above will wake you up. also not much for breakfast would have been nice to have orange juice...

Reviewed on Jun 2, 2025

Island Park Lodge

Island Park Lodge

2.5 out of 5
per person
Aug 25 - Aug 29
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Idaho Falls (IDA)
8.4/10 Very Good! (336 reviews)
Trash scattered all over walkway to rooms, AC not adequate for cooling, a lot of noise, walls are thin, pillows are flat as a pancake and need replaced. Bedding needs an upgrade. Overpriced for stay

Reviewed on Jun 16, 2025

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Chester Hotel Deals

Cozy, inviting log cabin near U.S. 20 on the way to Island Park and Yellowstone
Cozy, inviting log cabin near U.S. 20 on the way to Island Park and Yellowstone
Chester
$267 nightly
The price is $285 total per night from Jun 26 to Jun 27
$285 total
Jun 26 - Jun 27
Total includes taxes and fees
Peaceful
"I wish we could have stayed a little longer to utilize the firepit and outdoor area. It was nice to unplug for a bit with that back to basics home feel. No wifi, but excellent phone reception. A lot of history and character in the house. A few of our family members had a rough sleep in a few of the ..."

Reviewed on Apr 14, 2025

Cozy, inviting log cabin near U.S. 20 on the way to Island Park and Yellowstone
Tiny Cabin on the River (EV, Dog Friendly), Tiny Cabin on the River
Tiny Cabin on the River (EV, Dog Friendly), Tiny Cabin on the River
Fremont County
$166 nightly
The price is $177 total per night from Jun 29 to Jun 30
$177 total
Jun 29 - Jun 30
Total includes taxes and fees
Tiny Cabin on the River (EV, Dog Friendly), Tiny Cabin on the River
AmericInn by Wyndham Rexburg BYUI
AmericInn by Wyndham Rexburg BYUI
2.5 out of 5
1098 Golden Beauty Dr, Rexburg, ID
8.6/10 Excellent! (1,002 reviews)
"Easy to find, quiet. Unfortunately 2 lightbulbs were out in our room n leaving only 1 lightbulb available to light the sleeping area."

Reviewed on Jun 17, 2025

Get rates
AmericInn by Wyndham Rexburg BYUI
See all 259 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
Max Temp Winter
25ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Chester vacation package cost?
You can pick up a vacation package to this destination from $753 on Expedia. But how much your vacation to Chester costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Chester?
You can typically find reduced prices and greater availability in October, November and December. Take a look at our cheap Chester vacation packages and you could score some great off-season discounts.
How many days is enough for Chester?
With a well-planned itinerary, you can easily tick off the top Chester sights in a few days. But if you want to venture off the beaten track or go on day tours, consider booking your Chester vacation for longer.
How to find the best Chester package deals?
Use Expedia's handy filters to help you find some terrific Chester package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Chester package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your next Chester break by booking a customized vacation package. Click on the "Package" heading, then enter 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 rental car and you may score a better deal.
When to book a vacation package to Chester?
If you're planning an impromptu Chester getaway, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're anything like us, you love discovering new places but don't love the 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 cost of your Chester vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.