Chester Vacation Packages

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Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Wander Camp Yellowstone Island Park

Wander Camp Yellowstone Island Park

2 out of 5
per person
Jul. 20 - Jul. 27
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Idaho Falls (IDA)
8/10 Very Good! (423 reviews)
Quiet, beautiful spot, good breakfast

Reviewed on Sep. 20, 2024

Sawtelle Mountain Resort

Sawtelle Mountain Resort

2.5 out of 5
per person
Jul. 20 - Jul. 27
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Idaho Falls (IDA)
9.2/10 Wonderful! (1,002 reviews)
THIS hotel was super clean

Reviewed on Apr. 26, 2025

Island Park Lodge

Island Park Lodge

2.5 out of 5
per person
Jul. 20 - Jul. 27
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Idaho Falls (IDA)
8.4/10 Very Good! (315 reviews)
The room was well equipped with microwave, shampoo, Rinse, etc and reasonably priced. I would recommend this lodge to others.

Reviewed on Oct. 8, 2024

Blue Buffalo Resort

Blue Buffalo Resort

2 out of 5
per person
Jul. 20 - Jul. 27
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Idaho Falls (IDA)
9.4/10 Exceptional! (96 reviews)
We loved our stay at blue buffalo. The tiny upstairs loft was so fun for our four kids!

Reviewed on Feb. 18, 2025

Yellowstone Peaks Hotel

Yellowstone Peaks Hotel

4.5 out of 5
per person
Jul. 20 - Jul. 27
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Idaho Falls (IDA)
10/10 Exceptional! (47 reviews)
This place was very quiet and beautiful! There is all staff that you need. In addition, check in was very smoothly. My family very enjoy this trip. I strongly recommend this place.

Reviewed on Oct. 9, 2024

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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
The price is CA $241 per night from May 6 to May 7
CA $241
CA $422 total
includes taxes & fees
May 6 - May 7
9.8/10 Exceptional! (16 reviews)
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
The price is CA $110 per night from May 2 to May 3
CA $110
CA $243 total
includes taxes & fees
May 2 - May 3
Tiny Cabin on the River (EV, Dog Friendly), Tiny Cabin on the River
The Red Barn (EV), Barndominium on Henrys Fork
The Red Barn (EV), Barndominium on Henrys Fork
Fremont County
The price is CA $269 per night from May 7 to May 8
CA $269
CA $540 total
includes taxes & fees
May 7 - May 8
6/10 (2 reviews)
Comfortable rustic setting
"Exactly what you would expect of a cabin not inside a city or town."

Reviewed on Aug. 8, 2024

The Red Barn (EV), Barndominium on Henrys Fork
See all 244 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 $1,707 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.