Portland Vacations from $344

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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 $600, price is now $344 per person
$344
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,749 reviews)
Great Experience and loved the hotel. First time staying there.

Reviewed on Oct 15, 2025

H&O on Music Row

H&O on Music Row

4 out of 5
Music Row
Save 100% on your flight
Price was $974, price is now $569 per person
$569
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Nashville (BNA)
10/10 Exceptional! (4 reviews)
Good location, really nice apartment.

Reviewed on Jun 28, 2025

Hutton Hotel

Hutton Hotel

4.5 out of 5
West End
Save 100% on your flight
Price was $629, price is now $398 per person
$398
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
8.6/10 Excellent! (1,003 reviews)
The Hutton Hotel was very nice. I was super excited to stay there until I walked into my room and find not one but two chewed up tobacco pouches and the bathroom floor looked like it was swept or mopped. And the shower had hair, it’s like the bathroom was never cleaned.

Reviewed on Sep 28, 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,032, price is now $696 per person
$696
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (860 reviews)
Beautiful property. Staff was amazing. The Bar was beautiful. Room was beautiful.

Reviewed on Oct 12, 2025

Sleeps 24 12 Suites in Walkable Sobro Near Downtown by Avantstay

Sleeps 24 12 Suites in Walkable Sobro Near Downtown by Avantstay

3 out of 5
Downtown Nashville
Save 100% on your flight
Price was $6,104, price is now $4,271 per person
$4,271
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Nashville (BNA)
No reviews
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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

Wingate by Wyndham Goodlettsville

Wingate by Wyndham Goodlettsville

2.5 out of 5
202 Northgate Cir, Goodlettsville, TN
$65 nightly
The price is $80 total per night from Oct 26 to Oct 27
$80 total
Oct 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (1,049 reviews)
"Not much food for breakfast"

Reviewed on Oct 12, 2025

Wingate by Wyndham Goodlettsville
Spark by Hilton Nashville at Opryland

Spark by Hilton Nashville at Opryland

2 out of 5
2516 Music Valley Dr, Nashville, TN
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $88 total per night from Nov 2 to Nov 3
$88 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (203 reviews)
"This property was perfect and exactly what we were looking for. It smelt and felt and looked clean. There were a few cosmetic things around that could be fixed but I’ll take a paint chip here or there for clean and safe. The staff were friendly and helpful. Breakfast was the only area that could ..."

Reviewed on Oct 9, 2025

Spark by Hilton Nashville at Opryland
Comfort Inn Nashville - Opryland Area

Comfort Inn Nashville - Opryland Area

2.5 out of 5
2460 Music Valley Drive, Nashville, TN
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $101 total per night from Oct 28 to Oct 29
$101 total
Oct 28 - Oct 29
Total with taxes and fees
8.4/10 Very Good! (1,026 reviews)
Convenient location! .
"Room was very clean and bed was comfy."

Reviewed on Oct 12, 2025

Comfort Inn Nashville - Opryland Area
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.

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 $344 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.