Woodstock Vacations from $289

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Your Woodstock Vacation

Book a Woodstock vacation package and prepare to experience the best of this city. Consider basing yourself in the neighborhood of Mississippi District, which is good for shopping, nightlife and bars and pubs. If taking in sights is part of the program during your trip to Woodstock, visit top attractions like Oregon Zoo, Portland State University and Portland Japanese Garden. No matter your travel plans or the size of your budget, organizing your ultimate tailored Woodstock vacation is a breeze with Expedia.

The Latest Woodstock Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Siletz Bay Beachfront Hotel by OYO Lincoln City

Siletz Bay Beachfront Hotel by OYO Lincoln City

2 out of 5
Taft Historic District
Price was $414, price is now $289 per person
$289
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip flight included
Los Angeles (QLA) to Portland (PDX)
8.2/10 Very Good! (1,440 reviews)
Dog friendly with a charge.

Reviewed on Sep 2, 2025

Two Capes Lookout

Two Capes Lookout

2 out of 5
Save 100% on your flight
Price was $790, price is now $471 per person
$471
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.8/10 Exceptional! (59 reviews)
Beautiful well appointed cabins with excellent views of the ocean and surrounding forest on clear days. Our cabin was cozy with limited room. However they are comfortable considering the limited square footage.

Reviewed on Sep 2, 2025

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Save 100% on your flight
Price was $632, price is now $388 per person
$388
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,686 reviews)
This property was great for the downtown explorer… it was close to food, ice cream and shops. I love going to Multnomah village and Hawthorne area more. But the experience of staying downtown and on the 5th floor was nice. The bedding was so soft, and comfortable. The parking was secure and the complimentary bottle of wine was a nice touch.

Reviewed on Sep 1, 2025

SCP Depoe Bay

SCP Depoe Bay

3 out of 5
Price was $427, price is now $300 per person
$300
per person
Nov 7 - Nov 10
found 21 hours ago
Roundtrip flight included
Los Angeles (QLA) to Portland (PDX)
9.2/10 Wonderful! (540 reviews)
Wonderful staff, beautiful room. Comfortable bed, beautiful property, well maintained. Can't wait to return!

Reviewed on Aug 23, 2025

The Independence

The Independence

3 out of 5
Save 100% on your flight
Price was $667, price is now $471 per person
$471
per person
Oct 8 - Oct 12
found 7 hours ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.6/10 Exceptional! (919 reviews)
Clean rooms, private, quiet area.

Reviewed on Sep 1, 2025

Where to stay in Woodstock

Find the best Woodstock areas and neighborhoods for the activities you enjoy most. Learn more about Woodstock
Downtown Portland - South Waterfront showing picnicing, boating and a bay or harbor

Downtown Portland

4.5/5(4,488 area reviews)

Explore the Portland Art Museum, Oregon Historical Society, and Tom McCall Waterfront Park in this central business district with high-rise buildings. Enjoy walkable streets, and easily access public transportation like MAX light rail and Portland Streetcar.

Find hotels in Downtown Portland

Woodstock Hotel Deals

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $121 total per night from Sep 22 to Sep 23
$121 total
Sep 22 - Sep 23
Total with taxes and fees
The Paramount Hotel
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundable
$102 nightly
The price is $118 total per night from Sep 28 to Sep 29
$118 total
Sep 28 - Sep 29
Total with taxes and fees
Courtyard by Marriott Portland City Center
Holiday Inn Airport - Portland by IHG

Holiday Inn Airport - Portland by IHG

3 out of 5
8439 Ne Columbia Blvd, Portland, OR
Fully refundable
$90 nightly
The price is $104 total per night from Sep 28 to Sep 29
$104 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Airport - Portland by IHG
See all 2,700 properties in Woodstock
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Woodstock vacation package cost?
Browse and book everything in one place with our Woodstock vacation packages, which start from a low $289. Pick the hotels and flights that fit your travel plans. Then, add on a couple of activities or tours to round off your unique adventure.
How do I get a cheap travel package to Woodstock?
Think of all the awesome things you could do in Woodstock with a pile of extra cash in your pocket. Watch your savings stack up when you bundle your airfare and hotel bookings into a Woodstock vacation package. You have loads of choice when you book your trip with Expedia too. In fact, you can choose from over 550 air carriers and 1,000,000 hotels around the globe. Whether you're heading away with the entire family or surprising your special someone, exploring Woodstock is better with a package.
Where should I stay in Woodstock?
A trip to Woodstock isn't over until you've seen Oregon Zoo and Portland State University. Stay at a hotel within walking distance and easily access these popular tourist attractions.
What are the top hotels in Woodstock?
Get your escape off to a good start by booking a stay at Your Safe Haven In The Heart Of Metropolitan Portland. It's one of most popular hotels in Woodstock. Another comfortable option is Excellent Location, Close To Parks.
How far in advance should I book my Woodstock vacation?
Travelers are normally able to look up international fares on Expedia up to 12 months prior to departure. Booking late? With a little bit of luck, it's still possible to nab an affordable ticket just weeks before your flight.
What does an Expedia Woodstock travel package include?
Much of that is up to you. You can pick from a range of Woodstock bundles, such as a rental car, hotel and flight. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your perfect Woodstock vacation looks like, you're sure to save!
What should I know before booking a Woodstock travel package?
So many places to go, so many things to see and do. With a package, you'll be able to cross more of them off your list. Combine your hotels, rental cars and flights and enjoy big savings.
Can I choose my airline with a Woodstock Expedia vacation package?
You can, and with over 550 airlines to choose from globally, you're spoiled for choice. Scroll through the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Woodstock vacation package?
Don't stress if you're rethinking your Woodstock vacation package — it's possible to change or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We realize your circumstances can change suddenly, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we're ready to help.

Discover the most popular places to visit in Woodstock

Moda Center

Moda Center

4.5/5(1,165 reviews)

See sporting teams do battle and rock out to musical legends at one of Portland’s major venues for sports and big-ticket entertainment events.

Moda Center
Oregon Convention Center

Oregon Convention Center

4.5/5(569 reviews)

During your trip, find out what's happening at Oregon Convention Center, a top convention center in Portland. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Oregon Convention Center
Oregon Zoo featuring zoo animals and landscape views as well as a large group of people

Oregon Zoo

4.5/5(610 reviews)

Awesome beasts native to America have a home alongside exotic and endangered species from around the world at this picturesque Portland attraction.

Oregon Zoo

Things to do

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-hour Lunch Cruise on the Willamette River

$87
per adult
98% of travellers recommend
Portland: 2-hour Lunch Cruise on the Willamette River
Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

$85
per traveler
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

$7
per adult
Downtown Golden Adventure Quest Experience in Portland
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.