Portland Vacations from $398

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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.
Memoir Wedgewood Houston

Memoir Wedgewood Houston

4 out of 5
South Nashville
Save 100% on your flight
Price was $617, price is now $398 per person
$398
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.6/10 Exceptional! (71 reviews)
Amazing! Would come back to Nashville just to stay here.

Reviewed on Oct 26, 2025

Hutton Hotel

Hutton Hotel

4.5 out of 5
West End
Save 100% on your flight
Price was $1,160, price is now $588 per person
$588
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
8.6/10 Excellent! (1,003 reviews)
Everything was great, the staff were fantastic and incredibly helpful with everything

Reviewed on Nov 4, 2025

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $1,128, price is now $686 per person
$686
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.2/10 Wonderful! (894 reviews)
We had an early flight and our was ready by 7am! Staff was super friendly and the rooms are great!

Reviewed on Nov 6, 2025

The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
12 South
Save 100% on your flight
Price was $856, price is now $521 per person
$521
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.8/10 Exceptional! (158 reviews)
Everything was great. The only thing was tge expensive parking

Reviewed on Nov 8, 2025

Bluegreen Downtown Nashville

Bluegreen Downtown Nashville

2 out of 5
Downtown Nashville
Save 100% on your flight
Price was $806, price is now $501 per person
$501
per person
Jan 28 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (316 reviews)
The hotel was walking distance to everything downtown. The staff are very friendly and constantly check up on our stay. The room was clean and the bed was comfy. Great shower with tons of hot water. Great heritage building!

Reviewed on Nov 8, 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

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
$65 nightly
The price is $80 total per night from Nov 16 to Nov 17
$80 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (1,062 reviews)
The room was clean and staff was amazing, definitely recommend this place!

Reviewed on Oct 31, 2025

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
$116 nightly
The price is $138 total per night from Nov 16 to Nov 17
$138 total
Nov 16 - Nov 17
Total with taxes and fees
8.2/10 Very Good! (1,092 reviews)
Staff were very friendly and helpful. Room was clean however needs some updates. More plug in and ones that hold the plug in. Fan in the washrooms would be great. Carpet gone for sure. Breakfasts were great. Nice selection and fresh. The shuttle to the mall and Gaylords is a fantastic feature snd ...

Reviewed on Nov 5, 2025

Hyatt Place Nashville 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
$88 nightly
The price is $105 total per night from Nov 18 to Nov 19
$105 total
Nov 18 - Nov 19
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
Nice clean rooms, bathrooms, bedding, hallways, and eating area. Very good place to stay for the money. No thrills but didn’t need thrills here. Well maintained and very nice staff.

Reviewed on Oct 30, 2025

Comfort Inn Nashville - Opryland Area
See all 672 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 $398 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.