Chester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sawtelle Mountain Resort

Sawtelle Mountain Resort

2.5 out of 5
Price was CA $1,070, price is now CA $1,044 per person
CA $1,044
per person
Dec 29 - Jan 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Idaho Falls (IDA)
9.2/10 Wonderful! (1,023 reviews)

Timbers at Island Park Village Resort

Timbers at Island Park Village Resort

3 out of 5
Price was CA $1,519, price is now CA $1,320 per person
CA $1,320
per person
Dec 29 - Jan 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Idaho Falls (IDA)
8.8/10 Excellent! (478 reviews)

TroutHunter

TroutHunter

3.5 out of 5
Price was CA $1,143, price is now CA $1,077 per person
CA $1,077
per person
Dec 29 - Jan 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Idaho Falls (IDA)
10/10 Exceptional! (21 reviews)
It was clean. Location is beautiful. Good restaurant is on premise.

Reviewed on Jan 14, 2026

Starlight Retreat Yellowstone

Starlight Retreat Yellowstone

2 out of 5
Price was CA $1,241, price is now CA $1,179 per person
CA $1,179
per person
Dec 29 - Jan 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Idaho Falls (IDA)
8.4/10 Very good! (289 reviews)

Blue Buffalo Resort

Blue Buffalo Resort

3 out of 5
Price was CA $1,201, price is now CA $1,164 per person
CA $1,164
per person
Dec 29 - Jan 1
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Idaho Falls (IDA)
9.6/10 Exceptional! (836 reviews)

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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 ID
The price is CA $192 per night from Nov 13 to Nov 14
CA $192
CA $347 total
Nov 13 - Nov 14
includes taxes & fees
9.8/10 Exceptional! (43 reviews)
"Very Rustic!, the property would benefit with some minor upgrades and the addition of wifi & live t.v. . Great location and lots of room if you have a large group."

Reviewed on Oct 10, 2026

Cozy, inviting log cabin near U.S. 20 on the way to Island Park and Yellowstone
Cozy River View Cabin Near Yellowstone

Cozy River View Cabin Near Yellowstone

Chester ID
The price is CA $221 per night from Nov 13 to Nov 14
CA $221
CA $238 total
Nov 13 - Nov 14
includes taxes & fees
Cozy River View Cabin Near Yellowstone
Henry's Fork Inn

Henry's Fork Inn

2.5 out of 5
115 S Bridge St St. Anthony ID
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Nov 15 to Nov 16
CA $96
CA $103 total
Nov 15 - Nov 16
includes taxes & fees
Henry's Fork Inn
See all 270 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.
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Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from CA $1,044 on Expedia, you'll be thrilled with how little a vacation to Chester costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chester?
To pick up cheap Chester vacation packages, organize your getaway outside of peak times such as public holidays. You'll typically find lower prices and better availability for hotels and flights.
How many days is enough for Chester?
Usually, a handful of days is enough to explore the major sights during your Chester vacation. However, if you'd like to have time to chill out or go on day trips, think about extending your itinerary.
How to find the best Chester package deals?
Use Expedia's filters to find some great Chester package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Chester package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Chester escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
Score amazing discounts by booking your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Chester vacation.
How to plan a trip to Chester?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Chester.
  2. Plan your budget wisely: In addition to the cost of your hotel, you should factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Chester.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Chester. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Chester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.