Portland Vacations from $396

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Your Portland Vacation

When a getaway to the city is calling, answer it with a Portland vacation package. With all your travel plans worked out before you leave, all you have to do here is focus on making unforgettable memories. Wondering what you should do or see first during your trip to Portland? Head for popular attractions like Sumner Crest WInery. Whoever you're escaping with and whatever your budget, your dream Portland vacation is just clicks away with Expedia.

The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Nashville Airport

Sonesta Nashville Airport

4 out of 5
Save 100% on your flight
Price was $604, price is now $396 per person
$396
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,803 reviews)
The property was very nice and the staff was very friendly and helpful.

Reviewed on Dec 3, 2025

Hutton Hotel

Hutton Hotel

4.5 out of 5
West End
Save 100% on your flight
Price was $1,106, price is now $608 per person
$608
per person
Mar 2 - Mar 7
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
8.6/10 Excellent! (1,001 reviews)
Would stay again. Small rooms but good quality. Parking is well priced.

Reviewed on Dec 7, 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,602, price is now $974 per person
$974
per person
Feb 14 - Feb 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (924 reviews)
Rooms were very clean amenities were appropriate. However, it would’ve been nice to know ahead of time that there’s a $35 resort fee per night, which I did not see disclosed anywhere.

Reviewed on Dec 11, 2025

The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,011, price is now $671 per person
$671
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.6/10 Exceptional! (822 reviews)
Everything about our stay was perfect. The hotel is absolutely gorgeous and with the Christmas decorations it was even more spectactular. We ate in the restaurant for both dinner and breakfast. Both were great. Breakfast portions were hearty. Can’t wait to stay again soon.

Reviewed on Dec 9, 2025

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Discover the most popular places to visit in Portland

Sumner Crest WInery

You can enjoy a tasting or tour at Sumner Crest WInery during your travels to Portland. You can enjoy the coffeehouses while in the area.

Sumner Crest WInery

Portland Hotel Deals

Portland Inn & Suites

Portland Inn & Suites

2.5 out of 5
9239 Highway 52 Portland TN
Fully refundableReserve now, pay when you stay
7.2/10 Good! (320 reviews)
Nice comfortable accommodations

Reviewed on Nov 18, 2025

Get rates
Portland Inn & Suites
Wingate by Wyndham Goodlettsville

Wingate by Wyndham Goodlettsville

2.5 out of 5
202 Northgate Cir Goodlettsville TN
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,102 reviews)
Breakfast was good and room was clean

Reviewed on Dec 9, 2025

Get rates
Wingate by Wyndham Goodlettsville
Hyatt Place Nashville Opryland

Hyatt Place Nashville Opryland

3 out of 5
220 Rudy Cir Nashville TN
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $128 total per night from Dec 22 to Dec 23
$128 total
Dec 22 - Dec 23
Total with taxes and fees
8.2/10 Very Good! (1,143 reviews)
The front desk staff was over the top friendly. Very obvious that he loves his job. He made friends with everyone who walked through the door.

Reviewed on Dec 5, 2025

Hyatt Place Nashville Opryland
See all 676 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
Population
12,300
Max Temp Winter
45ºF
Max Temp Summer
85ºF

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Frequently asked questions

How much does a Portland vacation package cost?
You can grab a vacation package to this popular destination from $396 on Expedia. However, how much your vacation to Portland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Portland?
You're likely to find reduced prices and greater availability in July, October and November. Browse our cheap Portland vacation packages and you could score some great off-season discounts.
How many days is enough for Portland?
With a well-planned schedule, you can easily hit the most popular Portland sights in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your Portland vacation for longer.
How to find the best Portland package deals?
Use Expedia's filter tool to find some terrific Portland package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Portland package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Portland vacation as a package?
You can enjoy significant savings on your next Portland retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Portland?
If you're considering a spur-of-the-moment Portland vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Portland trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.

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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.