Chester Vacations

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Find the Best Chester Vacation Packages

Chester Hotel Deals

Katahdin Inn & Suites

Katahdin Inn & Suites

2 out of 5
740 Central St, Millinocket, ME
The price is ₩130,058 per night from Sep 5 to Sep 6
₩130,058
₩141,758 total
Sep 5 - Sep 6
includes taxes & fees
7.6/10 Good! (190 reviews)
"The room was clean and comfortable. Nice shower, hot water, cold A/C. Washer and dryer available and very helpful. Breakfast was good and the automatic pancake maker was fun with tasty results! Some remodeling going on so hot tub wasn't available and carpeting was partially new in spots. Weird smell ..."

Reviewed on Aug 17, 2025

Katahdin Inn & Suites
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 ₩200,076 per night from Aug 28 to Aug 29
₩200,076
₩218,084 total
Aug 28 - Aug 29
includes taxes & fees
8.4/10 Very Good! (491 reviews)
"IT was great and just right for what we needed. No down sides."

Reviewed on Aug 19, 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 ₩138,882 per night from Aug 27 to Aug 28
₩138,882
₩151,388 total
Aug 27 - Aug 28
includes taxes & fees
8.2/10 Very Good! (389 reviews)
"Place was clean and comfortable. Would gladly stay here again."

Reviewed on Aug 12, 2025

Gateway Inn
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.

Discover the most popular places to visit in Chester

Jato Highlands Golf Course

Enjoy a round of golf in Lincoln at Jato Highlands Golf Course. While you're in the area, stroll along the marina.

Jato Highlands Golf Course

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.