Chester Vacations from $442

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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.
Howard Johnson by Wyndham Bangor

Howard Johnson by Wyndham Bangor

2 out of 5
Price was $513, price is now $442 per person
$442
per person
Jan 6 - Jan 10
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
7.4/10 Good! (1,000 reviews)
The room is very nice. Spacious, modern and clean.

Reviewed on Dec 5, 2025

Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

3 out of 5
Price was $698, price is now $582 per person
$582
per person
Jan 6 - Jan 10
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
8.8/10 Excellent! (974 reviews)
The staff was awesome. The room was clean. Only downfall was the bed was not comfortable, but there was a beautiful view as well.

Reviewed on Nov 24, 2025

The Inn on Mount Desert

The Inn on Mount Desert

3 out of 5
Price was $642, price is now $537 per person
$537
per person
Jan 6 - Jan 10
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.6/10 Exceptional! (1,002 reviews)
beautiful room and property. nice staff. could not get heat in room regulated...way too hot. fortunately window opened and was fine. good breakfast and was nice selection

Reviewed on Nov 24, 2025

Belfast Harbor Inn

Belfast Harbor Inn

3.5 out of 5
Price was $676, price is now $577 per person
$577
per person
Jan 6 - Jan 10
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9.6/10 Exceptional! (1,000 reviews)
Nice hotel, very clean, good breakfast

Reviewed on Oct 23, 2025

Hollywood Casino Bangor

Hollywood Casino Bangor

3 out of 5
Price was $657, price is now $568 per person
$568
per person
Jan 6 - Jan 10
found 22 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
8.6/10 Excellent! (1,336 reviews)
Courteous front desk and bar staff - nice room

Reviewed on Dec 4, 2025

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Discover the most popular places to visit in Chester

Penobscot Valley Hospital

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 ME
9.2/10 Wonderful! (27 reviews)
This is the second time my friends and I stayed here. It is a great place and the hosts are fantastic.

Reviewed on Aug 24, 2025

Get rates
Cabin on the water!
Gateway Inn

Gateway Inn

2.5 out of 5
1963 Medway Road Medway ME
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $109 total per night from Dec 7 to Dec 8
$109 total
Dec 7 - Dec 8
Total with taxes and fees
8.4/10 Very Good! (431 reviews)
Room was very clean and had everything I needed. Check in was a breeze, staff members were very nice and friendly.

Reviewed on Dec 1, 2025

Gateway Inn
Briarwood Motor Inn

Briarwood Motor Inn

2.5 out of 5
223 West Broadway Lincoln ME
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $120 total per night from Jan 2 to Jan 3
$120 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.8/10 Excellent! (178 reviews)
Clean room and friendly staff

Reviewed on Nov 17, 2025

Briarwood Motor Inn
See all 112 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Population
550
Top Sights
Jato Highlands Golf Course and Lincoln Memorial Library

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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 $442 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.