Dexter Vacations from $604

Book a Hotel + Flight or Car together to unlock savings

Your Dexter Vacation

Pick a Dexter vacation package and you can focus on what matters — having some fun. There's no more planning nightmares, just a lot more free time to immerse yourself in the charms of this fascinating city, such as its small-town feel and friendly locals. Lake Wassookeag is just one of the top attractions to put on your sightseeing agenda during a trip to Dexter. Stop dreaming and start doing. Check out the wide range of options on Expedia today and finally put your Dexter vacation plans in motion!

The Latest Dexter vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Bangor by IHG

Holiday Inn Bangor by IHG

3 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 13
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Bangor (BGR)
7.8/10 Good! (1,003 reviews)
Easy off and on the highway and friendly staff

Reviewed on Jun 29, 2025

Eden Village Motel & Cottages

Eden Village Motel & Cottages

2.5 out of 5
Save 100% on your flight
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Bangor (BGR)
8.6/10 Excellent! (204 reviews)
Excellent property, with great hosts. Cabin one was perfect for 3 people and a dog!

Reviewed on Jun 25, 2025

3Bedroom2Bath CarriageHouse Pet Friendly

3Bedroom2Bath CarriageHouse Pet Friendly

3.5 out of 5
Save 100% on your flight
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Bangor (BGR)
7.4/10 Good! (3 reviews)
Loved the charm, cleanliness, decor and location. However, internet was so bad we couldn’t watch more than a few seconds of YouTube at a time. Upstairs shower had the lowest flow we’ve ever seen, even with volume turned up to maximum. Dishwasher was commercial and required many manual steps lifting basket, etc and special soap that we never found. Easier to hand wash. No laundry and outdoor light didn’t work at night so we stepped in dog pooh getting out of the car when we arrived. Beautiful little place that needs some attention.

Reviewed on Oct 11, 2023

Bar Harbor Main Street Apartments

Bar Harbor Main Street Apartments

3.5 out of 5
Downtown Bar Harbor
Save 100% on your flight
per person
Sep 10 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Bangor (BGR)
8/10 Very Good! (2 reviews)
Had a great experience at this property. Everything was very clean and well kept. Great apartment space and it was walking distance to everything in downtown.

Reviewed on Jul 2, 2025

3BedroomApt Pool CampFire PlayArea

3BedroomApt Pool CampFire PlayArea

3 out of 5
Save 100% on your flight
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Bangor (BGR)
8/10 Very Good! (2 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

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Discover the most popular places to visit in Dexter

Lake Wassookeag

5/5(1 review)

Commune with nature and explore the great outdoors at Lake Wassookeag during your travels in Dexter. Amble around the area's gardens or experience its entertainment venues.

Lake Wassookeag

Dexter Hotel Deals

Brewster Inn
Brewster Inn
3.5 out of 5
37 Zions Hill Road, Dexter, ME
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $182 total per night from Jul 5 to Jul 6
$182 total
Jul 5 - Jul 6
Total includes taxes and fees
Brewster in Fall
"The stay was amazing. The room was huge, the bed was comfortable, and the ayyention if the owners was impressive."

Reviewed on Nov 25, 2024

Brewster Inn
Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly
Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly
Dexter
9.4/10 Exceptional! (7 reviews)
"We really enjoyed our stay here. Quiet, shallow cove on the lake. Water at the.end of the dock is only waist high, so it's perfect for younger children. Nice cabin and the 2 upper bedrooms have air conditioning. Our group consisted of us...grandparents and two grandkids ages 6 and 9. This is definitely ..."

Reviewed on Jun 6, 2025

Get rates
Rustic, lakefront cabin with floating dock, firepit & fireplace - dog-friendly
Taylor Edes Inn
Taylor Edes Inn
3 out of 5
20 High Street, Dexter, ME
$149 nightly
The price is $162 total per night from Jul 7 to Jul 8
$162 total
Jul 7 - Jul 8
Total includes taxes and fees
9.6/10 Exceptional! (269 reviews)
"Very nice people Wonderful place, clean and enjoyable"

Reviewed on Jun 17, 2025

Taylor Edes Inn
See all 211 properties in Dexter
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 Dexter Vacation Packages

Dexter Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bangor Intl. Airport (BGR)
Population
2,200
Max Temp Winter
25ºF
Max Temp Summer
75ºF

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Frequently asked questions

How much does a Dexter vacation package cost?
You'll find cheap prices from $604 on Expedia for your Dexter break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Dexter costs.
What are the cheapest months to go to Dexter?
If you're hoping to snag a cheap Dexter vacation package, consider planning a trip in February, October and December. You'll typically find better prices on flights and hotels during these months --- perfect for budget-conscious travelers.
How many days is enough for Dexter?
With a well-planned schedule, you can easily hit the top Dexter attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, think about booking your Dexter vacation for longer.
How to find the best Dexter package deals?
Start your search for a Dexter package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few 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 irresistible savings. If you don't find the ideal Dexter package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Dexter escape off to a flying start.
Is it cheaper to book a Dexter vacation as a package?
You can enjoy significant savings on your Dexter escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Dexter?
Enjoy fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Dexter vacation.
Does Expedia offer Book Now, Pay Later Dexter vacation packages?
Set off on your dream trip to Dexter with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until your next payday --- we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.