Chester Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

Top hotels in Chester

Best Western Rose Quartz Inn

Best Western Rose Quartz Inn

2.5 out of 5
306 Main Street, Chester, CA
The price is S$319 per night from 6 Aug to 7 Aug
S$319
6 Aug - 7 Aug
includes taxes & fees
8.8/10 Excellent! (847 reviews)
"Web site said there was a pool but it was only a spa"

Reviewed on 12 Jul, 2025

Best Western Rose Quartz Inn
The Bidwell House

The Bidwell House

3.5 out of 5
#1 Main Street, Chester, CA
The price is S$307 per night from 17 Jul to 18 Jul
S$307
17 Jul - 18 Jul
includes taxes & fees
9.4/10 Exceptional! (171 reviews)
"Very clean, neat and tranquil. The host is very friendly. The rooms are very comfortable. The breakfast is excellent. I will be staying here again."

Reviewed on 2 Jul, 2025

The Bidwell House
The Village at Highlands Ranch

The Village at Highlands Ranch

2.5 out of 5
41500 Hwy 36E, Mill Creek, CA
The price is S$310 per night from 31 Jul to 1 Aug
S$310
31 Jul - 1 Aug
includes taxes & fees
8.6/10 Excellent! (252 reviews)
"Nice quiet place"

Reviewed on 12 Jul, 2025

The Village at Highlands Ranch
See all 276 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.

Frequently asked questions

How much does a Chester holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
December, January and February are the best times to look for cheap Chester holiday packages. Opting to travel in quieter months means you can typically find better prices on accommodation and flights.
How many days is enough for Chester?
Typically, a handful of days is enough to visit the main attractions during your Chester holiday. But if you prefer to have time to unwind or go on day tours, think about extending your itinerary.
How to find the best Chester package deals?
Use Expedia's filter tool to find some of the best 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 escape for midweek, or browse for Chester package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Chester holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking flights and accommodation individually. Better still, you can personalise your Chester getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Chester?
If you're planning a spur-of-the-moment Chester trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Chester?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Chester.
  2. Plan your budget wisely: As well as the cost of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may arise during your trip to Chester.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you want to get to in Chester. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Chester holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.