Portland Vacations from $345

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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.
Springhill Suites by Marriott Hartford Cromwell

Springhill Suites by Marriott Hartford Cromwell

2.5 out of 5
Price was $441, price is now $345 per person
$345
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hartford (BDL)
17.2/10 Exceptional! (641 reviews)
The front desk lady was professional and very pleasant and you could tell she likes her job and is a people-person

Reviewed on Nov 13, 2025

The Litchfield Inn

The Litchfield Inn

4 out of 5
Save 100% on your flight
Price was $945, price is now $659 per person
$659
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hartford (BDL)
9/10 Wonderful! (947 reviews)
Feel warm and comfy. But dont have restaurant in the house.

Reviewed on Nov 9, 2025

Hilton Garden Inn Hartford South/Glastonbury

Hilton Garden Inn Hartford South/Glastonbury

3 out of 5
Price was $633, price is now $489 per person
$489
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Hartford (BDL)
17.2/10 Exceptional! (1,000 reviews)
Nice pool. Plenty of parking. Some restaurants and bars within walking distance.

Reviewed on Nov 17, 2025

Homewood Suites by Hilton-Hartford South-Glastonbury, CT

Homewood Suites by Hilton-Hartford South-Glastonbury, CT

3 out of 5
Price was $540, price is now $429 per person
$429
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hartford (BDL)
8.8/10 Excellent! (1,005 reviews)
This is our "go to" spot when we visit in Glastonbury. It is well run, with courteous staff, clean, comfy rooms, and a very nice breakfast.

Reviewed on Nov 11, 2025

Home2 Suites by Hilton Bristol

Home2 Suites by Hilton Bristol

3 out of 5
Price was $501, price is now $400 per person
$400
per person
Feb 6 - Feb 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Hartford (BDL)
19.2/10 Exceptional! (157 reviews)
The kids enjoyed the pool. It was wonderful.

Reviewed on Nov 13, 2025

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Discover the most popular places to visit in Portland

Brownstone Exploration & Discovery Park

3.5/5(3 reviews)

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
$106 nightly
The price is $122 total per night from Nov 19 to Nov 20
$122 total
Nov 19 - Nov 20
Total with taxes and fees
8.6/10 Excellent! (212 reviews)
Room was a generous in size but very basic. Nothing fancy at all. You get what you pay for.

Reviewed on Oct 23, 2025

Solano Inn
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$83 nightly
The price is $95 total per night from Nov 23 to Nov 24
$95 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,149 reviews)
The room was great and the staff was really helpful...

Reviewed on Nov 7, 2025

Holiday Inn Express Southington by IHG
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Dec 14 to Dec 15
$102 total
Dec 14 - Dec 15
Total with taxes and fees
7.4/10 Good! (1,072 reviews)
It is such a fantastic view from my room, super clean, great amenities, comfy bed. The only mild criticism is they are out of regular coffee. Many people are coffee addicts and rely on regular coffee to wake up! Luckily I travel with some instant, so I poured a little into the delicious decaf Starbucks ...

Reviewed on Nov 13, 2025

The Capitol Hotel
See all 709 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 $345 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.