Portland Vacations from $428

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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.
Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
per person
Oct 24 - Oct 27
just found
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (1,007 reviews)
I didn’t like the carpets in the room - old and worn out.

Reviewed on Aug 17, 2025

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

4 out of 5
Downtown Hartford
per person
Oct 24 - Oct 27
just found
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
7.6/10 Good! (1,001 reviews)
It was walking distance to the concert we where going to. Along with I think that all hotels should have parking for their guest. Why should we have to pay for parking when we are already paying to stay at hotel just greedy for money.

Reviewed on Aug 9, 2025

Courtyard by Marriott Hartford Manchester

Courtyard by Marriott Hartford Manchester

3 out of 5
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Hartford (BDL)
8.4/10 Very Good! (901 reviews)
Stayed for 1 night, close to shopping & dining. Many enjoyed the pool. Customer service was great.

Reviewed on Aug 17, 2025

Hilton Garden Inn Hartford South/Glastonbury

Hilton Garden Inn Hartford South/Glastonbury

3 out of 5
per person
Oct 24 - Oct 27
just found
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (965 reviews)
We enjoyed a King Suite with separate bedroom. Fantastic! Excellent staff from front desk to kitchen & bar & excellent service on 6th floor.

Reviewed on Aug 9, 2025

Fairfield Inn & Suites Hartford Manchester

Fairfield Inn & Suites Hartford Manchester

2.5 out of 5
per person
Oct 24 - Oct 27
just found
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (1,002 reviews)
Very professional, friendly, helpful.

Reviewed on Aug 11, 2025

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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
$94 nightly
The price is $109 total per night from Aug 19 to Aug 20
$109 total
Aug 19 - Aug 20
Total includes taxes and fees
8.8/10 Excellent! (175 reviews)
"the room was nice and big. It felt homey not like every other hotel you still in! perfect for me and my husband on a trip."

Reviewed on Aug 3, 2025

Solano Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $97 total per night from Aug 26 to Aug 27
$97 total
Aug 26 - Aug 27
Total includes taxes and fees
7.4/10 Good! (1,007 reviews)
"Quiet downtown area. Ubers to other area like the Parkville Market, cheap rates."

Reviewed on Aug 16, 2025

The Capitol Hotel
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
351 Pitkin Steet, East Hartford, CT
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $136 total per night from Aug 31 to Sep 1
$136 total
Aug 31 - Sep 1
Total includes taxes and fees
9/10 Wonderful! (1,007 reviews)
Convenient and clean
"Hotel was queen. The free breakfast was a little disappointing. We were very late for check-in, but the front desk person was understanding and very nice."

Reviewed on Aug 15, 2025

Hampton Inn & Suites Hartford/East Hartford
See all 665 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.

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Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals from $428 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.