Portland Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Portland Holiday
Our pick of the best Portland Hotel Deals
Solano Inn
1503 Portland-Cobalt Rd Portland CT
Fully refundableReserve now, pay when you stay
NZ$160
19 Aug - 20 Aug
includes taxes & fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
NZ$179
30 Aug - 31 Aug
includes taxes & fees
8.6/10 Excellent! (1,416 reviews)
"It was ok a little dated breakfast was pretty good coffee was excellent ..."
Reviewed on 11 Aug 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
NZ$173
16 Aug - 17 Aug
includes taxes & fees
7.4/10 Good! (1,486 reviews)
"Rooms were not super clean, staff was friendly, free breakfast, parking garage is not ideal"
Reviewed on 12 Aug 2026
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
Arrigoni Winery
8.8/10 (6 reviews)
This rustic Connecticut vineyard crafts over 30 speciality wines and unique ciders in a countryside setting. Savour tastings on the vineyard-side patio while enjoying live music and made-to-order food.
Chris Cote's Toptracer Golf Range and Performance Center
Elevate your golf game at this tech-forward range with Toptracer technology tracking every swing in real time. Practice in heated bays or schedule a professional fitting session for personalised improvement.
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?
- Choose your travel dates: What you plan to do in Portland and your preferred season can help you decide when to get away.
- 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.
- 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.
- 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.
