Portland Vacations from $681

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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.
Solano Inn

Solano Inn

2.5 out of 5
Price was $840, price is now $681 per person
$681
per person
Apr 20 - Apr 25
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.8/10 Excellent! (219 reviews)
Nice room friendly people

Reviewed on Feb 23, 2026

Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Save 100% on your flight
Price was $1,021, price is now $742 per person
$742
per person
May 30 - Jun 6
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
No reviews
Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $1,957, price is now $1,478 per person
$1,478
per person
May 24 - May 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
9.8/10 Exceptional! (1,002 reviews)
Room, food, amenities and staff were all excellent!!

Reviewed on Feb 8, 2026

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $1,020, price is now $815 per person
$815
per person
May 24 - May 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8.8/10 Excellent! (1,004 reviews)
The staff was great building needed some updates our Lyft driver seem a little out of it direction, wise, etc.

Reviewed on Mar 8, 2026

Graduate by Hilton Storrs

Graduate by Hilton Storrs

4 out of 5
Price was $1,042, price is now $856 per person
$856
per person
Apr 20 - Apr 25
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
9.4/10 Exceptional! (1,007 reviews)
We had a brief but great experience. The staff was super friendly, the food and coffee were delicious and it was a perfect location and visit for the campus. The place is wonderfully decorated with amazing touches from the paintings to the rugs. It brought out a lot of Husky Pride. Thank you

Reviewed on Mar 10, 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 refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from Mar 26 to Mar 27
$127 total
Mar 26 - Mar 27
Total with taxes and fees
8.8/10 Excellent! (219 reviews)
Nice room friendly people

Reviewed on Feb 23, 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
$94 nightly
The price is $108 total per night from Mar 29 to Mar 30
$108 total
Mar 29 - Mar 30
Total with taxes and fees
7.6/10 Good! (1,202 reviews)
1) Great location. 2) Great views. 3) Good breakfast with hot options. 4) Reliable WiFi but it requires logging in every 24H, which means it can drop out in the middle of doing something. 5) The printer in the business center did not work (no toner). 6) They often lock the front door to the hotel, ...

Reviewed on Mar 18, 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
$108 nightly
The price is $124 total per night from Mar 22 to Mar 23
$124 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (1,234 reviews)
Clean rooms / easy check in and out / close to food-Gas-Walmart -Target

Reviewed on Mar 15, 2026

Holiday Inn Express Southington by IHG
See all 761 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 $681 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.