Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

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Your Portland Holiday

You'll find plenty to like about Portland, from its eclectic style to its cultural experiences and beyond. When you're ready to spend some time in this lively city, our Portland holiday packages will be ideal for you. If your trip to Portland includes some sightseeing, hit up famous attractions like Wesleyan University, TPC River Highlands and Dinosaur State Park. Check out Expedia's extensive range of travel options and book your dream holiday to Portland now.

Portland Holiday

Portland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
5,900
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Powder Ridge Mountain Park and Resort, Dinosaur State Park and Brownstone Exploration & Discovery Park

Our pick of the best Portland Hotel Deals

Solano Inn

Solano Inn

2.5 out of 5
1503 Portland-Cobalt Rd, Portland, CT
Fully refundableReserve now, pay when you stay
The price is AU$256 per night from 13 Aug to 14 Aug
AU$256
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (172 reviews)
"the room was nice and big. It felt homey not like every other hotel you still in! perfect for me and my husband on a trip."

Reviewed on 3 Aug. 2025

Solano Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 24 Aug to 25 Aug
AU$134
24 Aug - 25 Aug
includes taxes & fees
7.4/10 Good! (1,007 reviews)
Very pleasant
"Madeline at the front desk and all staff are very welcoming and professional. Hot breakfast is good and accomodations are clean and comfortable. GPS guided me into adjacent parking lot not affiliated with the hotel."

Reviewed on 9 Aug. 2025

The Capitol Hotel
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 7 Sept to 8 Sept
AU$178
7 Sept - 8 Sept
includes taxes & fees
7.4/10 Good! (1,004 reviews)
"Great job"

Reviewed on 8 Aug. 2025

Clarion Inn
See all 664 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Portland holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Portland costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Portland?
You can generally find lower rates and better availability in February, March and November. Browse our cheap Portland holiday packages and you could get some great off-season deals.
How many days is enough for Portland?
With a well-organised schedule, you can easily tick off the top Portland attractions in a few days. But if you'd like to venture off the beaten track or go on day trips, consider booking your Portland holiday for longer.
How to find the best Portland package deals?
Use Expedia's filter tool to help you find some great Portland package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Portland package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package as early as possible.
Is it cheaper to book a Portland holiday as a package?
You can enjoy significant savings on your Portland retreat by booking a customised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel and flight 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 holiday package to Portland?
Score fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Portland getaway.
How to plan a trip to Portland?

  1. Choose your travel dates: What you plan to do in Portland and your preferred season can help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and flights. Your accommodation will likely be the biggest expense during your trip to Portland.
  3. Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Portland. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodation and airfare: Once you've settled on your dates and duration, book the right Portland holiday package for you.

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