Portland Vacations from $335

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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 $545, price is now $335 per person
$335
per person
Mar 25 - Mar 28
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,803 reviews)
Everything was excellent!

Reviewed on Jan 4, 2026

The Hermitage Hotel

The Hermitage Hotel

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,086, price is now $715 per person
$715
per person
Mar 22 - Mar 25
found 16 hours 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

Caption by Hyatt Downtown Nashville

Caption by Hyatt Downtown Nashville

3 out of 5
Downtown Nashville
Save 100% on your flight
Price was $776, price is now $511 per person
$511
per person
Feb 14 - Feb 18
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (700 reviews)
Staff was amazing!! Convenient location to Broadway!

Reviewed on Jan 7, 2026

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,651, price is now $1,121 per person
$1,121
per person
Feb 14 - Feb 18
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (924 reviews)
Great and beautiful

Reviewed on Jan 7, 2026

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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
$80 nightly
The price is $93 total per night from Jan 9 to Jan 10
$93 total
Jan 9 - Jan 10
Total with taxes and fees
7.2/10 Good! (323 reviews)
Very courteous woman at the front desk. Beds were comfy, room was a nice size. Everything was clean! Excellent value for the price

Reviewed on Dec 20, 2025

Portland Inn & Suites
Hyatt Place Nashville Opryland

Hyatt Place Nashville Opryland

3 out of 5
220 Rudy Cir Nashville TN
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $120 total per night from Jan 15 to Jan 16
$120 total
Jan 15 - Jan 16
Total with taxes and fees
8.2/10 Very Good! (1,205 reviews)
Yes

Reviewed on Jan 5, 2026

Hyatt Place Nashville Opryland
Best Western Suites Near Opryland

Best Western Suites Near Opryland

2.5 out of 5
201 Music City Circle Nashville TN
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $96 total per night from Jan 25 to Jan 26
$96 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (1,441 reviews)
clean room

Reviewed on Jan 2, 2026

Best Western Suites Near Opryland
See all 684 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 $335 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.