Chester Vacations from $1,037

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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.
The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $1,293, price is now $1,037 per person
$1,037
per person
Apr 30 - May 4
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Bangor (BGR)
9.8/10 Exceptional! (376 reviews)
Cleaner carpet much more better and next time I give 5 star. This is not complain just wonder hotel get all 5 stars

Reviewed on Mar 23, 2026

Hearthside Inn

Hearthside Inn

2.5 out of 5
Price was $1,733, price is now $1,470 per person
$1,470
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
9.8/10 Exceptional! (213 reviews)
The owner was very friendly and kind. The room was beautiful but we were surprised to not have any parking options nearby or a bathroom in the room. The breakfast was delicious, but was definitely small portions and didn’t fill my husband. Overall though nice place. Just unfortunate the things that are challenging most likely can’t be changed other than the food.

Reviewed on Dec 25, 2025

3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
Price was $1,424, price is now $1,208 per person
$1,208
per person
Jun 7 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
8/10 Very Good! (3 reviews)
Nice spot that is very close to bar harbor. Very clean and great for a large amount of people.

Reviewed on Jun 30, 2025

Historic 2 Cats Inn

Historic 2 Cats Inn

3 out of 5
Price was $1,575, price is now $1,343 per person
$1,343
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Bangor (BGR)
8.4/10 Very Good! (5 reviews)
Staff was excellent both the Inn and the Restaurant. Responsive to our messages and very helpful. Can’t wait to go back in the future.

Reviewed on Sep 30, 2025

Fireside Inn & Suites - Belfast

Fireside Inn & Suites - Belfast

3 out of 5
Price was $1,269, price is now $1,092 per person
$1,092
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Bangor (BGR)
9/10 Wonderful! (1,008 reviews)
The view was great and the room was comfortable. I had no issues with my stay and would recommended this inn to others.

Reviewed on Mar 13, 2026

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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

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 Mar 28 to Mar 29
$109 total
Mar 28 - Mar 29
Total with taxes and fees
8.4/10 Very Good! (438 reviews)
Pretty nice place to stay

Reviewed on Mar 20, 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
$155 nightly
The price is $169 total per night from Mar 31 to Apr 1
$169 total
Mar 31 - Apr 1
Total with taxes and fees
Baxter Park Inn
Katahdin Inn & Suites

Katahdin Inn & Suites

2 out of 5
740 Central St Millinocket ME
$138 nightly
The price is $150 total per night from Apr 21 to Apr 22
$150 total
Apr 21 - Apr 22
Total with taxes and fees
7.6/10 Good! (260 reviews)
Friendly staff, large clean rooms, good location for snowmobiling trails & gas, ample parking.

Reviewed on Feb 8, 2026

Katahdin Inn & Suites
See all 114 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 $1,037 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.