Chester Vacations

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Find the Best Chester Vacation Packages

Chester Hotel Deals

Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.

Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.

Chester ME
10/10 Exceptional! (1 review)
"The lodge was exactly what we were looking for. It comfortably slept 4 and the HVAC kept it cool despite a hot week in Maine. Jim was a great host. He clearly communicated everything, met us at check in, and had the lodge stocked with toiletries, snacks, and some drinks. He’s thought of everything. ..."

Reviewed on Jul 9, 2026

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Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.
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 ￥18,713 per night from Jul 21 to Jul 22
￥18,713
￥20,397 total
Jul 21 - Jul 22
includes taxes & fees
8.6/10 Excellent! (569 reviews)
"I don't remember reading that there were cats in the Lobby. I am allergic so I try to keep away but needed to use the laundry. The room was fine and the bed was comfortable. The staff was great and friendly. The side parking lot needs to be levelled out. There were a few dips but manageable. Overall, ..."

Reviewed on Jul 10, 2026

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 ￥16,237 per night from Jul 15 to Jul 16
￥16,237
￥17,699 total
Jul 15 - Jul 16
includes taxes & fees
8.4/10 Very Good! (458 reviews)
"Parking was great. Disappointed that the indoor pool was no longer a thing there. :-("

Reviewed on Jul 13, 2026

Gateway Inn
See all 135 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.

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