Chester Trips (flight + hotel)

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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 P9,020 per night from Jul 6 to Jul 7
P9,020
P9,832 total
Jul 6 - Jul 7
includes taxes & fees
8.4/10 Very Good! (475 reviews)
"The hotel was conveniently located. The building and grounds were a little tired but the staff was clearly making an effort."

Reviewed on Jun 30, 2025

Baxter Park Inn
Gateway Inn
Gateway Inn
2.5 out of 5
1963 Medway Road, Medway, ME
Fully refundableReserve now, pay when you stay
The price is P5,635 per night from Jul 5 to Jul 6
P5,635
P6,142 total
Jul 5 - Jul 6
includes taxes & fees
8.2/10 Very Good! (375 reviews)
Nice!
"Friendly staff and very clean room!! Nice interior. Would stay again!!"

Reviewed on Jun 29, 2025

Gateway Inn
Katahdin Inn & Suites
Katahdin Inn & Suites
2 out of 5
740 Central St, Millinocket, ME
7.8/10 Good! (143 reviews)
"Was there for a basketball tournament- the place was hopping and the staff was great - so many teenagers with family - it was perfect for time spent there - wouldn’t hesitate to stay there again"

Reviewed on Jun 29, 2025

Get rates
Katahdin Inn & Suites
See all 111 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 vacation package cost?
You can pick up a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation 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 vacation. 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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and stays separately. Better still, you can personalize 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 vacation 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 vacation package.

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