Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Ready to book your vacation to Portland?

 

Choose your dates

Portland Hotel Deals

Harlow's Casino Resort & Spa

Harlow's Casino Resort & Spa

3.5 out of 5
4280 Harlow's Blvd Greenville MS
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 3 to Nov 4
CA $162
CA $179 total
Nov 3 - Nov 4
includes taxes & fees
8/10 Very good! (1,000 reviews)
"The restaurant did not open until 10 in the morning"

Reviewed on Oct 27, 2026

Harlow's Casino Resort & Spa
Hotel 27

Hotel 27

2 out of 5
211 South Walnut Street Greenville MS
The price is CA $134 per night from Nov 4 to Nov 5
CA $134
CA $147 total
Nov 4 - Nov 5
includes taxes & fees
9/10 Wonderful! (375 reviews)
"The hotel was SO cool!! It is the only not-for-profit hotel in Mississippi! They put money back into the community by supporting small businesses and schools. The staff were amazing and very helpful in pointing out great places to eat. The room was clean, had a great table for playing games. The ..."

Reviewed on Oct 17, 2026

Hotel 27
Tru By Hilton Greenville

Tru By Hilton Greenville

2.5 out of 5
600 Rayner Road Greenville MS
Fully refundableReserve now, pay when you stay
The price is CA $194 per night from Nov 8 to Nov 9
CA $194
CA $213 total
Nov 8 - Nov 9
includes taxes & fees
8/10 Very good! (640 reviews)
"10 out of 10 will recommend very great customer service even housekeeping"

Reviewed on Oct 25, 2026

Tru By Hilton Greenville
See all 42 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
Family Vacations

Frequently asked questions

How much does a Portland vacation package cost?
You can grab a vacation package to this destination on Expedia. However, how much your vacation to Portland costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Portland?
You can usually find reduced prices and greater availability in January, February and November. Explore our cheap Portland vacation packages and you could get some excellent off-season deals.
How many days is enough for Portland?
The ideal length for your Portland vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the leading sights and discover some hidden spots along the way.
How to find the best Portland package deals?
Bagging a cheap Portland package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a couple of filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Portland package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can tailor your Portland getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Portland?
If you've got your Portland vacation dates finalized, book as early as you can to bag some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Portland?

  1. Choose when to travel: Check your schedule and get packing. Your favourite time of year and the available activities will also help you decide when to escape to Portland.
  2. Set a budget: Consider costs like flights, food and transportation when calculating how much to put aside for your trip to Portland. Then, choose a hotel that matches your budget, whether that's a wallet-friendly option or a swankier retreat.
  3. Decide how long to go away for: Now that you're up to speed on Portland, you can figure out the ideal length of your break. Put together a draft plan and give yourself enough time to cover everything you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Portland vacation package that brings all your bookings together.

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