Portland Holidays

Photo by Rick Bucchino
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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Portland

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 S$179 per night from 23 Jun to 24 Jun
S$179
23 Jun - 24 Jun
includes taxes & fees
8.8/10 Excellent! (138 reviews)
Nice stay
"Room was large, clean and comfortable. We enjoyed our two night stay. The room could easily accomodate an easy chair, or two,which be appreciated."

Reviewed on 3 Jun, 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 S$152 per night from 1 Jul to 2 Jul
S$152
1 Jul - 2 Jul
includes taxes & fees
7.4/10 Good! (1,013 reviews)
"Thanks to Staff name Hasani. He helped us out and directed perfectly with all questions and concerns."

Reviewed on 8 Jun, 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 S$141 per night from 23 Jun to 24 Jun
S$141
23 Jun - 24 Jun
includes taxes & fees
7.4/10 Good! (1,009 reviews)
"Very comfortable"

Reviewed on 9 Jun, 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.