Portland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Portland Vacation Packages

Portland Hotel Deals

Cozy Lake-View Cottage for 4 Ā· Wine Tasting Included Ā· Pet Friendly

Cozy Lake-View Cottage for 4 Ā· Wine Tasting Included Ā· Pet Friendly

Portland NY
The price is SARĀ 777 per night from Jul 19 to Jul 20
SARĀ 777
SARĀ 1,371 total
19 Jul - 20 Jul
includes taxes & fees
10/10 Exceptional! (58 reviews)
"After a day of traveling, enjoying the local winery was a great way to relax."

Reviewed on 25 June 2026

Cozy Lake-View Cottage for 4 Ā· Wine Tasting Included Ā· Pet Friendly
Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
125 W Lake Rd Mayville NY
Fully refundableReserve now, pay when you stay
The price is SARĀ 507 per night from Jul 20 to Jul 21
SARĀ 507
SARĀ 573 total
20 Jul - 21 Jul
includes taxes & fees
6.8/10 (263 reviews)
"Strange, large, octagonal opening in the wall that connects the bathroom to the bedroom, thus no bathroom privacy at all. No television. They had to bring a cable box, install it completely and then gave a remote control that was not connected to the box, and only could access 4 channels, 3 of which ..."

Reviewed on 13 July 2026

Webb's Year Round Resort
Clarion Hotel Conference Center on Lake Erie

Clarion Hotel Conference Center on Lake Erie

2.5 out of 5
30 Lake Shore Dr E Dunkirk NY
Fully refundable
The price is SARĀ 474 per night from Aug 12 to Aug 13
SARĀ 474
SARĀ 536 total
12 Aug - 13 Aug
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"First: TV didnā€™t work and they switched us to a room where the TV controller could not be located. There was no mini refrigerator and was told you had to order it when making reservations. Who does that! And last there was a urine stain at the bottom sheet near feet that if you didnā€™t pull the sheet ..."

Reviewed on 16 July 2026

Clarion Hotel Conference Center on Lake Erie
See all 467 properties in Portland
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.

Stay near popular Portland attractions

21 Brix Winery

You can enjoy a tasting or tour at 21 Brix Winery during your travels to Portland.
See properties

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Portland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Portland?
Plan your trip for the low season and you're likely to get cheap Portland vacation packages. Keep in mind that school vacation periods and major festivals and events can impact prices, so do a little research before you go.
How to find the best Portland package deals?
Begin your search for a Portland package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," 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 Portland package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Portland escape off to a flying start.
Is it cheaper to book a Portland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the flexibility to create a customized Portland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Portland?
If you're considering a spur-of-the-moment Portland vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Portland?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to visit Portland.
  2. Set your budget: Consider costs like transportation, flights and meals when working out how much to put aside for your trip to Portland. Then, choose a property that suits your budget, whether that's an economical option or a more upscale getaway.
  3. Decide how long to go for: Now that you know more about Portland, you can figure out the ideal length of your break. Create a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Portland vacation package.