Portland Vacations from $511

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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 Torrington

Days Inn by Wyndham Torrington

2 out of 5
Price was $585, price is now $511 per person
$511
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
7.4/10 Good! (1,013 reviews)
Convenient location. Everything was good, not great. Met expectations for the price and location. Solid three stars all-around. Room was comfortable, but a bit small. No dresser or drawers. Front desk staff was friendly, but overworked. Nobody there when we went to check in an when we went back the next morning to get a room key fixed. Overall condition is a bit tired, but they said that renovations are underway.

Reviewed on Oct 13, 2025

Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

2.5 out of 5
Price was $773, price is now $672 per person
$672
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
5.6/10 (768 reviews)
Walls are thin but it was clean and safe with friendly staff.

Reviewed on Oct 14, 2025

The Goodwin Hotel

The Goodwin Hotel

3.5 out of 5
Downtown Hartford
Price was $796, price is now $695 per person
$695
per person
Dec 30 - Jan 1
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
9/10 Wonderful! (1,005 reviews)
Friendly staff, well located just garage was tricky. It’s across the street but on weekends the grated gate it down so you have to either call the attendant or have vallet guy wand you through.

Reviewed on Oct 13, 2025

Courtyard by Marriott Hartford Cromwell

Courtyard by Marriott Hartford Cromwell

3 out of 5
Price was $1,041, price is now $913 per person
$913
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (688 reviews)
Great location and friendly and helpful staff.

Reviewed on Sep 25, 2025

Homewood Suites by Hilton Hartford-Farmington

Homewood Suites by Hilton Hartford-Farmington

3 out of 5
Price was $775, price is now $684 per person
$684
per person
Nov 25 - Nov 29
found 16 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.4/10 Very Good! (1,005 reviews)
The only problem is the potholes and deep drains on the entrance and exit that have not been repaired for the last year.

Reviewed on Oct 18, 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
$132 nightly
The price is $152 total per night from Nov 2 to Nov 3
$152 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (204 reviews)
"Outside is a bit dated apparently it used to be under different name and ownership but the room is amazing. It’s a bit off the beaten path but it’s easy short ride from Middletown. I got a room last minute. Room is large with large tv and king size bed. Very cute decor with small fridge with freezer ..."

Reviewed on Oct 13, 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
$98 nightly
The price is $113 total per night from Nov 16 to Nov 17
$113 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,136 reviews)
"Nice place"

Reviewed on Oct 18, 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
$103 nightly
The price is $118 total per night from Oct 20 to Oct 21
$118 total
Oct 20 - Oct 21
Total with taxes and fees
7.4/10 Good! (1,022 reviews)
"Room was clean and comfortable. Staff were amazing"

Reviewed on Oct 12, 2025

The Capitol Hotel
See all 687 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.

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 $511 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.