Portland Holidays

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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$193 per night from 19 July to 20 July
AU$193
19 July - 20 July
includes taxes & fees
8.6/10 Excellent! (249 reviews)
"The room clean and decorated in away that was comfortable and eye appealing. The remote for the TV was a little touchy. They had wine glasses and glass drinking glasses in the cupboard by the coffee maker and mini fridge . That was an unexpected positive"

Reviewed on 7 July 2026

Solano Inn
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Fully refundableReserve now, pay when you stay
The price is AU$123 per night from 4 Aug to 5 Aug
AU$123
4 Aug - 5 Aug
includes taxes & fees
7/10 Good! (1,211 reviews)
"Book for double twin. Was told since we checked in later in the night the room was given away. Room smelled moldy and the gap in the door at the bottom was at least 1/2 inch. Big enough for any bugs or small vermin to get through. Would not stay there again. Checked out as soon as I woke up and ..."

Reviewed on 7 July 2026

Motel 6 Wethersfield, CT - Hartford
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd Hartford CT
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 2 Aug to 3 Aug
AU$171
2 Aug - 3 Aug
includes taxes & fees
7.8/10 Good! (1,091 reviews)
"Nice clean place to stay for business travel"

Reviewed on 8 July 2026

Best Western Hartford Hotel & Suites
See all 725 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

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.
See properties

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.

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