Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chester

Baxter Park Inn

Baxter Park Inn

2 out of 5
935 Central St, Millinocket, ME
Fully refundableReserve now, pay when you stay
The price is 3.763.899 ₫ per night from 31 Jul to 1 Aug
3.763.899 ₫
4.102.673 ₫ total
31 Jul - 1 Aug
includes taxes & fees
8.4/10 Very Good! (483 reviews)
"Very comfortae stay at Baxter Park Inn. Extremely friendly hosts (including the cats!)."

Reviewed on 15 Jul 2025

Baxter Park Inn
Katahdin Inn & Suites

Katahdin Inn & Suites

2 out of 5
740 Central St, Millinocket, ME
7.8/10 Good! (168 reviews)
Post Kahtadin
"Comfortable, spacious and clean."

Reviewed on 24 Jul 2025

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Katahdin Inn & Suites
Gateway Inn

Gateway Inn

2.5 out of 5
1963 Medway Road, Medway, ME
Fully refundableReserve now, pay when you stay
The price is 2.612.693 ₫ per night from 22 Aug to 23 Aug
2.612.693 ₫
2.847.953 ₫ total
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (385 reviews)
"I was a nice place to spend the night . The staff was very friendly. The hotel was very quiet and very clean."

Reviewed on 27 Jul 2025

Gateway Inn
See all 112 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 holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday to Chester costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Chester?
To score cheap Chester holiday packages, plan your trip outside of peak periods like public holidays and major events. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Chester?
Typically, a handful of days is enough to see the top attractions during your Chester holiday. However, if you prefer to have more time to relax or take day tours, consider extending your itinerary.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Chester package deal straight away, just tweak 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 holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can personalise your Chester escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Chester?
If you're planning a spontaneous Chester adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Chester?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred season and the available activities will also help you decide when to visit Chester.
  2. Work out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and experiences. Your hotel will likely be the biggest expense during your trip to Chester.
  3. Decide how many days away: Start by compiling a list of the activities and sights you want to get to in Chester. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Chester holiday package.