Chester Vacation Packages
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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.
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
3BedroomApt Pool CampFire PlayArea
Price was CA $3,271, price is now CA $2,963 per person
CA $2,963
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) 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
Hilton Garden Inn Bangor
Price was CA $1,056, price is now CA $961 per person
CA $961
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Bangor (BGR)
9/10 Wonderful! (1,013 reviews)
Was conveniently located to I95, would be nice to have shuttle to downtown
Reviewed on Aug. 26, 2025
Chester Hotel Deals
Baxter Park Inn
935 Central St, Millinocket, ME
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Aug 31 to Sep 1
CA $198
CA $216 total
Aug 31 - Sep 1
includes taxes & fees
Katahdin Inn & Suites
740 Central St, Millinocket, ME
The price is CA $131 per night from Sep 25 to Sep 26
CA $131
CA $143 total
Sep 25 - Sep 26
includes taxes & fees
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.