Portland Vacations from $393

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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.
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
Price was $499, price is now $393 per person
$393
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Hartford (BDL)
6.8/10 (1,529 reviews)
Air conditioner in room was extremely loud, had to sit it off to sleep. Refrigerator was also loud. This room did not compare to the excellent room I had stayed in the week before.

Reviewed on Aug 23, 2025

Las Flores Villa

Las Flores Villa

5 out of 5
Save 100% on your flight
Price was $2,716, price is now $1,776 per person
$1,776
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
10/10 Exceptional! (1 review)
DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

4 out of 5
Downtown Hartford
Price was $803, price is now $617 per person
$617
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
7.6/10 Good! (1,002 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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
Price was $545, price is now $431 per person
$431
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Hartford (BDL)
8.4/10 Very Good! (989 reviews)
Staff was extremely kind

Reviewed on Aug 19, 2025

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $541, price is now $428 per person
$428
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (1,006 reviews)
Conveniently located, with plenty of places around. Staff was very friendly and helpful.

Reviewed on Aug 24, 2025

Don't see what you're looking for?
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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
$80 nightly
The price is $93 total per night from Aug 27 to Aug 28
$93 total
Aug 27 - Aug 28
Total with taxes and fees
8.8/10 Excellent! (176 reviews)
"Good quality for the price. I would stay here again."

Reviewed on Aug 23, 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 31 to Sep 1
$97 total
Aug 31 - Sep 1
Total with taxes and fees
7.6/10 Good! (1,013 reviews)
"It was good"

Reviewed on Aug 24, 2025

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
$100 nightly
The price is $115 total per night from Sep 25 to Sep 26
$115 total
Sep 25 - Sep 26
Total with taxes and fees
8.6/10 Excellent! (1,067 reviews)
"Beds comfortable. Breakfast selection good."

Reviewed on Aug 19, 2025

Holiday Inn Express Southington by IHG
See all 674 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 $393 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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