Cutler Vacations from $567

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Your Cutler Vacation

Our Cutler vacation packages give you the power to create your own adventure. Tailor your getaway to your style and interests and make every moment count in this wonderful city. Every trip to Cutler needs a well-planned itinerary. Fill yours with leading attractions like The Bold Coast, Cutler Coast Public Reserved Land and Bog Brook Cove. Browse Expedia's extensive range of travel options and book your ultimate vacation to Cutler today.

The Latest Cutler vacation packages

Price found within the past 48 hours. Click for updated prices.
Kimball Terrace Inn Northeast Harbor

Kimball Terrace Inn Northeast Harbor

2.5 out of 5
Price was $591, price is now $567 per person
$567
per person
Oct 19 - Oct 22
just found
Roundtrip flight included
Chicago (ORD) to Bar Harbor (BHB)
9/10 Wonderful! (1,012 reviews)
Close by marina Sadly the staff did not manage to collect and forward a item that was sent to them for my attention. Instead they refused the item and now I have a hassle to get it re shipped. In spite of phone messages and phone cals to make this happen this was a stumble, so not good.

Reviewed on Sep 16, 2025

White Birches Motel

White Birches Motel

2.5 out of 5
Price was $1,366, price is now $1,186 per person
$1,186
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bar Harbor (BHB)
7.4/10 Good! (1,009 reviews)
Older Motel, nicely updated. New Kitchenette area (sink, counter, cooking area very nice!) staff all friendly and nice. Great location for us.

Reviewed on Sep 15, 2025

Elsa's Inn on the Harbor

Elsa's Inn on the Harbor

2 out of 5
Price was $916, price is now $797 per person
$797
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bar Harbor (BHB)
9.4/10 Exceptional! (181 reviews)
We had a wonderful stay at Elsa's Inn! Friendly, helpful owner and staff providing great recommendations and information about the area, delicious breakfasts, and a beautiful home.

Reviewed on Sep 8, 2025

Ferncrest Acadia

Ferncrest Acadia

2 out of 5
Price was $1,414, price is now $1,242 per person
$1,242
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bar Harbor (BHB)
No reviews
Elegant Suite with Jacuzzi

Elegant Suite with Jacuzzi

3 out of 5
Price was $1,018, price is now $928 per person
$928
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Bar Harbor (BHB)
8.8/10 Excellent! (8 reviews)
Exactly what the picture showed, very nice and spacious. Grocery store is close by as well as a Walmart.

Reviewed on Sep 3, 2025

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Cutler Hotel Deals

Oceanfront Home; A Coastal Maine Woodland Retreat

Oceanfront Home; A Coastal Maine Woodland Retreat

Cutler
9.8/10 Exceptional! (97 reviews)
"Beautiful house with plenty of room. Great views and family enjoyed the house and beach area very much. Nice and clean house with just enough nautical charm. We enjoyed our stay."

Reviewed on Sep 6, 2025

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Oceanfront Home; A Coastal Maine Woodland Retreat
Elegant log home with unobstructed ocean views

Elegant log home with unobstructed ocean views

Cutler
9.8/10 Exceptional! (62 reviews)
"Beautiful home base for exploring the Bold Coast!"

Reviewed on Aug 20, 2025

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Elegant log home with unobstructed ocean views
Harbor View Cottage Maine, 150+ years old

Harbor View Cottage Maine, 150+ years old

Cutler
9.8/10 Exceptional! (31 reviews)
"We have stayed here before. It is such a great location. Love spending time in Chester. Feels like a second home"

Reviewed on Jul 25, 2025

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Harbor View Cottage Maine, 150+ years old
See all 262 properties in Cutler
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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Frequently asked questions

How much does a Cutler vacation package cost?
You can snap up a vacation package to this top destination from $567 on Expedia. However, how much your vacation to Cutler costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Cutler?
November, December and January are great times to search for cheap Cutler vacation packages. Opting to travel in quieter months means you can usually find better prices on hotels and flights.
How many days is enough for Cutler?
The ideal length for your Cutler vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to tick off all the major attractions and explore some hidden spots along the way.
Is it worth booking a vacation package to Cutler?
Popular for its culture, walking trails and hiking, a Cutler vacation is a hit with all types of travelers. Be sure to visit top sights like The Bold Coast and Cutler Coast Public Reserved Land, and consider renting some wheels for day trips to experience even more.
How to find the best Cutler package deals?
Landing a cheap Cutler package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Cutler package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Cutler vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can personalize your Cutler getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Cutler?
Land amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Cutler getaway.
Does Expedia offer Book Now, Pay Later Cutler vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Cutler trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.