Chester Holidays

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Top hotels in Chester

Quaint 1 Bedroom + Loft/1 Bath streamside Timber Frame cabin near Lincoln, ME.

Quaint 1 Bedroom + Loft/1 Bath streamside Timber Frame cabin near Lincoln, ME.

Chester ME
10/10 Exceptional! (3 reviews)
"The cabin was great for my me and my son while we visited Maine to climb Mt. Katahdin! Clean and perfectly located for activities around northern Maine. The host was excellent and very accommodating to all our asks! Thanks for helping make our trip a memorable experience!"

Reviewed on 4 Oct 2026

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Quaint 1 Bedroom + Loft/1 Bath streamside Timber Frame cabin near Lincoln, ME.
Gateway Inn

Gateway Inn

2.5 out of 5
1963 Medway Road Medway ME
Fully refundableReserve now, pay when you stay
The price is €97 per night from 6 Nov to 7 Nov
€97
6 Nov - 7 Nov
includes taxes & fees
8.6/10 Excellent! (514 reviews)
"Great service, friendly staff, poor continental breakfast."

Reviewed on 1 Nov 2026

Gateway Inn
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 €136 per night from 6 Nov to 7 Nov
€136
6 Nov - 7 Nov
includes taxes & fees
Baxter Park Inn
See all 142 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?
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.

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