
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
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
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


The Pathmaker Hotel
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
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
Chester Hotel Deals

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

Baxter Park Inn
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

Gateway Inn
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
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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