Chesuncook Vacations from $844
Book a Hotel + Flight or Car together to unlock savings
The Latest Chesuncook Vacation Packages
- Robbins Motel
Oct 15 - Oct 21Robbins Motel + Flight
Bar Harbor6 nights2.5 star property5.4/10 - (598 reviews)"It is by far the absolute WORST hotel in Maine, maybe America. It should be condemned & the staff is soooo nasty. Our sink was falling off the wall & she said we'll I refund you but we dont care itll be booked immediately. There was a huge gap under the door because there was a bug chunk missing from it. Its horrible but its cheap. The only cheap hotel in Bar Harbor"Reviewed July 27, 2026Roundtrip • Chicago (CHI) - Bangor (BGR)ORD - BGR • Nonstop BGR - ORD • 1 stop$1,101$844found 1 day agoper traveler - Hinckleys Dreamwood Cottages
Oct 15 - Oct 21Hinckleys Dreamwood Cottages + Flight
Bar Harbor6 nights3.0 star property7.8/10 - Good (107 reviews)"Perfect spot"Reviewed July 27, 2026Roundtrip • Chicago (CHI) - Bangor (BGR)ORD - BGR • Nonstop BGR - ORD • 1 stop - 3Bedroom2Bath CarriageHouse Pet Friendly
Oct 15 - Oct 213Bedroom2Bath CarriageHouse Pet Friendly + Flight
Bar Harbor6 nights3.5 star property8.0/10 - 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 September 30, 2025Roundtrip • Chicago (CHI) - Bangor (BGR)ORD - BGR • Nonstop BGR - ORD • 1 stop - 3BedroomApt Pool CampFire PlayArea
Oct 15 - Oct 213BedroomApt Pool CampFire PlayArea + Flight
Bar Harbor6 nights3.0 star property8.0/10 - Very Good (3 reviews)"Nice spot that is very close to bar harbor. Very clean and great for a large amount of people. "Reviewed June 30, 2025Roundtrip • Chicago (CHI) - Bangor (BGR)ORD - BGR • Nonstop BGR - ORD • 1 stop - Beautiful Bar Harbor House
Oct 15 - Oct 21Beautiful Bar Harbor House + Flight
Bar Harbor6 nights4.0 star propertyRoundtrip • Chicago (CHI) - Bangor (BGR)ORD - BGR • Nonstop BGR - ORD • 1 stop
Frequently Asked Questions
How much does a Chesuncook vacation package cost?
Offering great value package deals from $844 on Expedia, you'll be thrilled with how little a vacation to Chesuncook costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Chesuncook?
October, November and December are the best times to search for cheap Chesuncook vacation packages. Traveling in quieter months means you can usually find lower prices on flights and accommodations.
How many days is enough for Chesuncook?
Generally, a handful of days is enough to go to the major sights during your Chesuncook vacation. However, if you want to have some time to unwind or take day trips, consider extending your trip.
How to find the best Chesuncook package deals?
Bagging a cheap Chesuncook package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a couple of filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most economical Chesuncook package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Chesuncook vacation as a package?
You can enjoy significant savings on your next Chesuncook getaway by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chesuncook?
Secure amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chesuncook getaway.
Does Expedia offer Book Now, Pay Later Chesuncook vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Chesuncook vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.