Portland Vacations from $355

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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.
Fairfield Inn & Suites Hartford Manchester

Fairfield Inn & Suites Hartford Manchester

2.5 out of 5
Price was $410, price is now $355 per person
$355
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8.6/10 Excellent! (1,002 reviews)
Near highways and shopping/ restaurants. Very convenient

Reviewed on Aug 18, 2025

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $439, price is now $372 per person
$372
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8.6/10 Excellent! (1,007 reviews)
Mon seul point négatif est au sujet de la cafétéria. Elle est plutôt petite et il n’y avait aucun fruit au déjeuner.

Reviewed on Aug 18, 2025

Holiday Inn Express Hartford South - Rocky Hill by IHG

Holiday Inn Express Hartford South - Rocky Hill by IHG

2.5 out of 5
Price was $503, price is now $427 per person
$427
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8.6/10 Excellent! (1,000 reviews)
It was wonderful. I needed a room last minute and they were able to accommodate. The guest service was excellent and very resourceful.

Reviewed on Aug 15, 2025

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $790, price is now $675 per person
$675
per person
Oct 9 - Oct 11
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
9.8/10 Exceptional! (1,000 reviews)
Beautiful hotel, safe area, walk to shopping and restaurants. The staff was extremely nice and accommodating.

Reviewed on Aug 11, 2025

Courtyard by Marriott Hartford Manchester

Courtyard by Marriott Hartford Manchester

3 out of 5
Price was $416, price is now $359 per person
$359
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

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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
$97 nightly
The price is $111 total per night from Aug 21 to Aug 22
$111 total
Aug 21 - Aug 22
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 21 to Aug 22
$97 total
Aug 21 - Aug 22
Total includes taxes and fees
7.4/10 Good! (1,022 reviews)
"Thank you for having us and our dogs. Nice spot to be."

Reviewed on Aug 18, 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
$108 nightly
The price is $124 total per night from Aug 24 to Aug 25
$124 total
Aug 24 - Aug 25
Total includes taxes and fees
8.6/10 Excellent! (1,067 reviews)
"It was walking distance to Thompson’s point where the music festival I went to see was being held. The staff from the front desk to cleaning staff, were all very friendly. More hooks and/or towel bars in the bathroom. Other than the shelf/rack that all the towels were stored on that is IN THE SHOWER ..."

Reviewed on Aug 15, 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 $355 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.