Chester Vacations from $481

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Your Chester Vacation

Art, food, entertainment and more … There's so much to discover with a Chester vacation package. And with the ability to easily customize your city break, it's guaranteed to be one that's tough to forget. In the mood for a bit of sightseeing? A trip to Chester isn't complete without exploring Lincoln Memorial Library, Jato Highlands Golf Course and other popular attractions. Don't delay visiting this destination any longer. Your dream Chester vacation is a couple of clicks away with Expedia.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Cedar Crest Inn

Cedar Crest Inn

2.5 out of 5
per person
Oct 29 - Nov 3
found 2 hours ago
Roundtrip flight included
Denver (DEN) to Bangor (BGR)
8.8/10 Excellent! (645 reviews)
It was a nice motel for a very reasonable price. Small spaces but certainly adequate. Staff was pleasant.

Reviewed on Aug 6, 2025

The Primrose

The Primrose

3 out of 5
Save 100% on your flight
per person
Oct 29 - Nov 3
found 2 hours ago
Roundtrip flight included
Denver (DEN) to Bangor (BGR)
9.6/10 Exceptional! (927 reviews)
The Primrose was wonderful !! Welcoming ... room was perfect..... breakfast delicious . I would love to go back again !!!

Reviewed on Aug 4, 2025

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
8.6/10 Excellent! (222 reviews)
Clean, so adorable inside. The property is excellent.

Reviewed on Aug 2, 2025

High Tide Inn

High Tide Inn

2 out of 5
per person
Sep 20 - Sep 27
found 1 hour ago
Roundtrip non-stop flight included
Detroit (DTW) to Bangor (BGR)
9/10 Wonderful! (259 reviews)
Enjoyed the sitting outside and watching the ocean. Saw eagles and wild turkeys. Since I booked with Expedia we were not given the continental breakfast. Needed to pay $12 each for the breakfast. We declined paying for the breakfast.

Reviewed on Aug 10, 2025

Mount Battie Inn

Mount Battie Inn

2.5 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Bangor (BGR)
8.8/10 Excellent! (301 reviews)
The owner is wonderful, the property is charming, old-style, and lovely (although the rooms had a strong smell that was not comfortable for us); we enjoyed our stay. It's a great location! Full of history and charm.

Reviewed on Jul 28, 2025

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Discover the most popular places to visit in Chester

Penobscot Valley Hospital

4/5(1 review)

Though Penobscot Valley Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Lincoln while you are here.

Penobscot Valley Hospital

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

Chester Hotel Deals

Cabin on the water!

Cabin on the water!

Chester
9.4/10 Exceptional! (24 reviews)
"We had a very relaxed, quiet, and comfortable stay!"

Reviewed on Jul 21, 2025

Get rates
Cabin on the water!
Katahdin Inn & Suites

Katahdin Inn & Suites

2 out of 5
740 Central St, Millinocket, ME
$99 nightly
The price is $108 total per night from Sep 5 to Sep 6
$108 total
Sep 5 - Sep 6
Total includes taxes and fees
7.6/10 Good! (180 reviews)
"Something happened with my reservation here with my bank and a 3rd party app. So my reservation got canceled. I called the hotel and Cory answered and was very understanding and very helpful. I thought I was roomless over 1000 miles from home but he saved the day. He blocked a family suite so when ..."

Reviewed on Aug 7, 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
$160 nightly
The price is $174 total per night from Aug 12 to Aug 13
$174 total
Aug 12 - Aug 13
Total includes taxes and fees
8.4/10 Very Good! (487 reviews)
"Room was standard, staff was excellent, willing to help with any questions and concerns I had! Just your basic hotel!"

Reviewed on Aug 6, 2025

Baxter Park Inn
See all 110 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 vacation package cost?
You can pick up a vacation package to this top destination from $481 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?
July, September and December are great times to look for cheap Chester vacation packages. Opting to travel in quieter months means you can generally find better prices on flights and accommodations.
How many days is enough for Chester?
The ideal length of your Chester vacation depends on what you'd like to see and do. Typically, a few days to a week will give you plenty of time to tick off all the main sights and discover some hidden treasures along the way.
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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Chester trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.