Portland Vacation Packages

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Your Portland Vacation

The eclectic style and cultural experiences are just the beginning of the things Portland has going for it. Discover the sights and sounds of this city the way you want with a personalized Portland vacation package. A trip to Portland is an ideal opportunity to do a bit of sightseeing. Check out renowned attractions like Wesleyan University, Brownstone Exploration & Discovery Park and TPC River Highlands. Expedia can help you escape the everyday. Tailor your vacation to Portland to suit your style of travel, whatever that may be!

Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
8.2/10 Very Good! (845 reviews)
Nice facility. Desk Clerk very accommodating

Reviewed on Apr. 3, 2025

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

4 out of 5
Downtown Hartford
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
7.6/10 Good! (1,003 reviews)
Easy off the highway. Friendly staff. Easy check in.

Reviewed on Mar. 24, 2025

Delamar West Hartford

Delamar West Hartford

4 out of 5
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
9.8/10 Exceptional! (951 reviews)
We had an enjoyable stay after attending an event. Room was great!

Reviewed on Mar. 8, 2025

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
8.4/10 Very Good! (939 reviews)
I would definitely stay here again

Reviewed on Mar. 26, 2025

Best Western Manchester

Best Western Manchester

2.5 out of 5
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
8.6/10 Excellent! (32 reviews)
New clean and comfortable

Reviewed on Mar. 30, 2025

Ready to book your vacation to Portland?

 

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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 CA $96 per night from Apr. 22 to Apr. 23
CA $96
CA $111 total
includes taxes & fees
Apr 22 - Apr 23
9.2/10 Wonderful! (99 reviews)
Good location and price
"My stay at the Solano Inn was fine. Nothing fancy, but that's ok since the cost was less than I expected to find in the area. The staff were all very kind and helpful. I was quite concerned that they made a copy of my credit card at check in. I've traveled a lot but never had that happen before. ..."

Reviewed on Mar. 30, 2025

Solano Inn
The Capitol Hotel, Ascend Hotel Collection
The Capitol Hotel, Ascend Hotel Collection
3 out of 5
440 Asylum St, Hartford, CT
7.4/10 Good! (1,000 reviews)
"Excellent"

Reviewed on Mar. 30, 2025

Get rates
The Capitol Hotel, Ascend Hotel Collection
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Apr. 6 to Apr. 7
CA $121
CA $139 total
includes taxes & fees
Apr 6 - Apr 7
7.2/10 Good! (1,001 reviews)
"Personnel are nice and polite but room temperature thermostat is hard to control"

Reviewed on Apr. 1, 2025

Clarion Inn
See all 657 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

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals from CA $856 on Expedia, you’ll be pleasantly surprised at how much a vacation 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 vacation packages and you could get some great off-season deals.
How many days is enough for Portland?
With a well-organized 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 vacation 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 vacation package as early as possible.
Is it cheaper to book a Portland vacation as a package?
You can enjoy significant savings on your Portland retreat by booking a customized vacation 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 vacation 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 accommodations 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 accommodations and airfare: Once you’ve settled on your dates and duration, book the right Portland vacation package for you.

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