Chester Vacations from $663

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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.
Hinckleys Dreamwood Cottages

Hinckleys Dreamwood Cottages

3 out of 5
Price was $880, price is now $663 per person
$663
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Bangor (BGR)
7.6/10 Good! (98 reviews)
Staff was wonderful plus some ! Cabin a bit musty but opened windows & everything was great. Cabin was very clean & bed was comfortable !!! Loved the girl that checked us in - Little confusion on my part & she couldn’t have been sweeter ❤️ AND… they just put in a pool !

Reviewed on Jul 14, 2026

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
Price was $946, price is now $699 per person
$699
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Bangor (BGR)
8.8/10 Excellent! (267 reviews)
We stayed in the motel portion. The location is convenient and our room was ok, but the bathroom had a sliding door with no locking mechanism, which is quite ridiculous when there is a family staying in the room. When I emailed the property twice about this, both emails were ignored. Similarly, I messaged them with a request for "late" checkout (11 am, since their checkout is a ridiculously early 10 am), I received no response.

Reviewed on Jul 13, 2026

Moseley Cottage Inn & Town Motel

Moseley Cottage Inn & Town Motel

3 out of 5
Downtown Bar Harbor
Price was $1,174, price is now $889 per person
$889
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Bangor (BGR)
9.4/10 Exceptional! (589 reviews)
Cozy and well maintained

Reviewed on Jul 14, 2026

The Pathmaker Hotel

The Pathmaker Hotel

2 out of 5
Price was $1,228, price is now $946 per person
$946
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Bangor (BGR)
9.8/10 Exceptional! (549 reviews)
Great place to stay, great location. Short walk to Bar Island crossing and lots of restaurants and shops with a grocery store across the street. Helpful and friendly staff.

Reviewed on Jul 15, 2026

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Save 100% on your flight
Price was $2,156, price is now $1,681 per person
$1,681
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Bangor (BGR)
8/10 Very Good! (4 reviews)
It was beautiful inside and out. Would recommend 10/10. Very quiet location beds slept great and close to Bar Harbor

Reviewed on Sep 30, 2025

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Chester Hotel Deals

Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.

Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.

Chester ME
10/10 Exceptional! (1 review)
"The lodge was exactly what we were looking for. It comfortably slept 4 and the HVAC kept it cool despite a hot week in Maine. Jim was a great host. He clearly communicated everything, met us at check in, and had the lodge stocked with toiletries, snacks, and some drinks. He’s thought of everything. ..."

Reviewed on Jul 9, 2026

Get rates
Quaint 1 Bedroom/1 Bath streamside Timber Frame cabin minutes from Lincoln, ME.
Baxter Park Inn

Baxter Park Inn

2 out of 5
935 Central St Millinocket ME
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $170 total per night from Jul 18 to Jul 19
$170 total
Jul 18 - Jul 19
Total with taxes and fees
8.6/10 Excellent! (569 reviews)
"I don't remember reading that there were cats in the Lobby. I am allergic so I try to keep away but needed to use the laundry. The room was fine and the bed was comfortable. The staff was great and friendly. The side parking lot needs to be levelled out. There were a few dips but manageable. Overall, ..."

Reviewed on Jul 10, 2026

Baxter Park Inn
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 Jul 16 to Jul 17
$109 total
Jul 16 - Jul 17
Total with taxes and fees
8.4/10 Very Good! (458 reviews)
"Parking was great. Disappointed that the indoor pool was no longer a thing there. :-("

Reviewed on Jul 13, 2026

Gateway Inn
See all 135 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 $663 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.