Dayton Vacations from $728

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Your Dayton Vacation

Book a customized Dayton vacation package that includes everything you need and no unnecessary extras. Good for views, watersports and coastal beaches, think about staying in the neighborhood of Ocean Park. If some sightseeing is on your to-do list during your trip to Dayton, check out top attractions such as Swan Pond. Browse Expedia's wide range of travel options and begin planning your dream vacation to Dayton today.

The Latest Dayton vacation packages

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 178 Middle Street

The Docent's Collection at 178 Middle Street

Downtown Portland
$728
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (70 reviews)
This place was wonderful! The staff was incredibly helpful and it was a time location for things to do and places to eat, all within walking distance. Would definitely recommend and stay again

Reviewed on Oct 7, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

West End
$813
per person
Dec 19 - Dec 22
found 17 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (193 reviews)
Adorable stylish house and spacious room comfortable bed. Worth the walk to old port. Will come back!

Reviewed on Oct 6, 2026

Inn By The Sea

Inn By The Sea

$931
per person
Dec 10 - Dec 13
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (333 reviews)
Evalina Hotel

Evalina Hotel

Downtown Portland
$916
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
10/10 Exceptional! (13 reviews)
Centrally located in the Old Port, with views of the harbor, this was a last minute — therefore pricey — excellent find for a fall weekend getaway. Stylish, elegant rehab of 19th century granite industrial building. Whimsical decor notes referring to 19th century owner Evalina Fox. Nicely appointed kitchenette — though if you came to Portland for the foodie scene, you might end up just using it for breakfast, as we did. Only sour note was the disco music (coming in via the ventilation system?) from a nearby establishment audible during business hours. Well, if you pick a hotel in the middle of things, you get the noise and bustle that comes from being in the middle of things. That said, we’d come again, but shoot for a penthouse/upper floor unit farther from the street-level mania.

Reviewed on Oct 5, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

Downtown Portland
$774
per person
Dec 10 - Dec 13
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (400 reviews)
We thoroughly enjoyed our stay. We loved our one bedroom King loft. While we didn’t need the kitchenware it was fully stocked and very nice to have it. The staff, especially Jennifer was very helpful. We loved the location and were able to walk to everything in old port. The rooms were comfortable and quiet and nicely decorated. The parking in the back was very convenient and we were happy to have a space to easily get in and out when we wanted to enjoy areas outside of old port.

Reviewed on Oct 9, 2026

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What to do in Dayton

Kennebunkport Historic Walking Tour

Kennebunkport Historic Walking Tour

$35
per adult
Kennebunkport Historic Walking Tour
Relaxing Saco River Public Sunset Sail

Relaxing Saco River Public Sunset Sail

$149
per adult
Relaxing Saco River Public Sunset Sail
Private Two Hour Sail on the Saco River

Private Sailing Experience along the Southern Maine Coastline

$747
per traveler
Private Sailing Experience along the Southern Maine Coastline
See all activities in Dayton

Dayton Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME
Fully refundable
$83 nightly
$92 total
Nov 1 - Nov 2
Total with taxes and fees
Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

157 High St Portland ME
Fully refundableReserve now, pay when you stay
$135 nightly
$149 total
Nov 1 - Nov 2
Total with taxes and fees
The Westin Portland Harborview
Fireside Inn & Suites Portland

Fireside Inn & Suites Portland

81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
$85 nightly
$94 total
Oct 25 - Oct 26
Total with taxes and fees
Fireside Inn & Suites Portland
See all 3,907 properties in Dayton
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 Dayton Vacation Packages

Dayton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Population
1,800
Top Sights
Biddeford City Theater, Swan Pond and Mardens Surplus and Salvage

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Frequently asked questions

How much does a Dayton vacation package cost?
You'll find cheap prices from $728 on Expedia for your Dayton escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Dayton costs.
What are the cheapest months to go to Dayton?
If you're hoping to snag a cheap Dayton vacation package, consider visiting in May, August and December. You're likely to find lower prices on flights and accommodations during these months — ideal for budget-conscious travelers.
How many days is enough for Dayton?
The ideal length of your Dayton vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to hit all the main sights and discover some hidden gems along the way.
How to find the best Dayton package deals?
Use Expedia's filters to find some tempting Dayton package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Dayton package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Dayton vacation as a package?
You can enjoy significant savings on your next Dayton break by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Dayton?
Land fantastic discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Dayton adventure.
Does Expedia offer Book Now, Pay Later Dayton vacation packages?
If you're like us, you love traveling but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Dayton trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.