Portland Vacations from $398

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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!

The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
South Meadows
Price was $499, price is now $398 per person
$398
per person
Aug 21 - Aug 23
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
7.8/10 Good! (1,073 reviews)
Easy parking, clean, free breakfast

Reviewed on May 29, 2026

Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $950, price is now $727 per person
$727
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
9.8/10 Exceptional! (1,002 reviews)
we loved the service . I know this sounds silly but we loved the soap its my favorite .

Reviewed on May 30, 2026

Grantmoore Motor Lodge

Grantmoore Motor Lodge

2 out of 5
Save 100% on your flight
Price was $3,705, price is now $3,047 per person
$3,047
per person
Jul 24 - Jul 26
found 21 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
4.2/10 (74 reviews)
Dirty broken stinky 😣 it was not a clean place the attendance seems not to know what was going on inside the rooms because it was broken things inside.It was loud !

Reviewed on Sep 28, 2019

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 out of 5
Price was $771, price is now $651 per person
$651
per person
Jul 5 - Jul 12
found 4 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Hartford (BDL)
7.2/10 Good! (932 reviews)
Stayed one night. What was great. Staff, clean, comfortable bed, parking

Reviewed on May 31, 2026

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $662, price is now $560 per person
$560
per person
Jul 16 - Jul 19
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8.6/10 Excellent! (1,002 reviews)
Clean and convenient facilities, friendly and helpful staff, delicious breakfast.

Reviewed on May 27, 2026

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Discover the most popular places to visit in Portland

Brownstone Exploration & Discovery Park

Have a fun-filled day with the family at Brownstone Exploration & Discovery Park during your visit to Portland. Experience the festivals and entertainment venues in this family-friendly area.

Brownstone Exploration & Discovery Park

Arrigoni Winery

You can enjoy a tasting or tour at Arrigoni Winery during your travels to Portland. Experience the festivals and entertainment venues in this family-friendly area.

Arrigoni Winery

Portland Hotel Deals

Solano Inn

Solano Inn

2.5 out of 5
1503 Portland-Cobalt Rd Portland CT
Fully refundable
$133 nightly
The price is $153 total per night from Jun 8 to Jun 9
$153 total
Jun 8 - Jun 9
Total with taxes and fees
8.6/10 Excellent! (235 reviews)
"It’s not what I expected. Pictures online are deceiving."

Reviewed on May 17, 2026

Solano Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Jun 14 to Jun 15
$123 total
Jun 14 - Jun 15
Total with taxes and fees
7.4/10 Good! (1,346 reviews)
"The overall experience was good, however a fire alarm woke us up at 6:30 in the morning. Unfortunately we stayed at the top floor and my partner on a walker would not have been able to negotiate the fire stairs. I had indicated with the reservation that I am traveling with a handicapped person and ..."

Reviewed on Jun 1, 2026

The Capitol Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$112 nightly
The price is $128 total per night from Jun 29 to Jun 30
$128 total
Jun 29 - Jun 30
Total with taxes and fees
8.6/10 Excellent! (1,317 reviews)
"Blood stained sheets, dirty tiles and floors, hairs and bugs in sink... gross, for a holiday inn I was shocked, this was more the standard of a roadside truck stop."

Reviewed on Jun 1, 2026

Holiday Inn Express Southington by IHG
See all 740 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.

Find the Best Portland Vacation Packages

Portland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
5,900
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brownstone Exploration & Discovery Park, Dinosaur State Park and Powder Ridge Mountain Park and Resort

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Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals from $398 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 typically find lower prices and greater availability in June, July and December. Explore our cheap Portland vacation packages and you could get some excellent off-season deals.
How many days is enough for Portland?
With a well-planned schedule, you can easily tick off the main Portland attractions in a handful of days. But if you want to discover hidden spots or go on day tours, 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.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
Your Portland break should be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.