Gateway Vacations from $525

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The Latest Gateway vacation packages

Price found within the past 48 hours. Click for updated prices.
Canyon Rim at Eagle Crest

Canyon Rim at Eagle Crest

4.5 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 21
found 16 hours ago
Roundtrip flight included
San Diego (SAN) to Redmond (RDM)
9.2/10 Wonderful! (10 reviews)
The Aerie Suites by AvantStay – Modern Comfort with Mountain Views

The Aerie Suites by AvantStay – Modern Comfort with Mountain Views

3 out of 5
Summit West
Save 100% on your flight
per person
Sep 7 - Sep 14
found 16 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Redmond (RDM)
10/10 Exceptional! (1 review)
The Quilty of the condo. Beds were very comfortable.

Reviewed on Jun 15, 2025

Quiet River Bend Cabin by Avantstay 35 Mins to Mt Bachelor 10 Mins to Town Centre Hot Tub!

3.5 out of 5
Deschutes River Woods
Save 100% on your flight
per person
Sep 7 - Sep 14
found 16 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Redmond (RDM)
No reviews
Brasada Ranch

Brasada Ranch

4 out of 5
Save 100% on your flight
per person
Aug 30 - Sep 2
found 14 hours ago
Roundtrip flight included
Seattle (SEA) to Redmond (RDM)
9.4/10 Exceptional! (289 reviews)
Loved the room and trail ride

Reviewed on Jun 15, 2025

Frosty Summit Condo at Mount Bachelor

Frosty Summit Condo at Mount Bachelor

3.5 out of 5
Century West
per person
Sep 7 - Sep 14
found 16 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Redmond (RDM)
10/10 Exceptional! (3 reviews)
Great outdoor options nearby. Mountain bike trails really close. Very comfortable condo located in Bachelor resorts. Pretty view of forest off the balcony.

Reviewed on Jun 21, 2025

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Discover the most popular places to visit in Gateway

St. Charles - Madras

Though St. Charles - Madras might be what brings you to town, perhaps you'll have a chance to explore more of Madras while you are here.

St. Charles - Madras

Gateway Hotel Deals

The Inn at Cross Keys Station
The Inn at Cross Keys Station
2.5 out of 5
66 NW Cedar Street, Madras, OR
Fully refundableReserve now, pay when you stay
$166 nightly
The price is $183 total per night from Jul 13 to Jul 14
$183 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Two issues with this property—slick surface in shower and broken window latches."

Reviewed on Jul 3, 2025

The Inn at Cross Keys Station
The Bunk House at Cross Keys
The Bunk House at Cross Keys
2.5 out of 5
706 NW Bunkhouse Rd, Madras, OR
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $204 total per night from Jul 9 to Jul 10
$204 total
Jul 9 - Jul 10
Total includes taxes and fees
9.6/10 Exceptional! (261 reviews)
"Great stay! Nice rooms and great breakfast. Highly recommend!"

Reviewed on Jul 3, 2025

The Bunk House at Cross Keys
Motel 6 Madras, OR
Motel 6 Madras, OR
2 out of 5
1539 Us 97, Madras, OR
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $94 total per night from Jul 8 to Jul 9
$94 total
Jul 8 - Jul 9
Total includes taxes and fees
7.8/10 Good! (707 reviews)
"Our room was huge compared to other chain hotels! Very clean and well maintained room and property. Convenient location. Only downside...no coffee maker!"

Reviewed on Jul 3, 2025

Motel 6 Madras, OR
See all 29 properties in Gateway
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 Gateway Vacation Packages

Gateway Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Gateway vacation package cost?
You can snap up a vacation package to this popular destination from $525 on Expedia. However, how much your vacation to Gateway costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Gateway?
If you're hoping to book a cheap Gateway vacation package, consider visiting in December, January and February. You'll typically find better prices on hotels and flights during these months --- perfect for travelers wishing to save money.
How many days is enough for Gateway?
With a well-organized travel plan, you can easily hit the most popular Gateway sights in a few days. But if you prefer to discover lesser-known spots or go on day trips, consider booking your Gateway vacation for longer.
How to find the best Gateway package deals?
Use Expedia's filter tool to find some of the best Gateway package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Gateway package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Gateway vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can customize your Gateway getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Gateway?
Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Gateway trip.
Does Expedia offer Book Now, Pay Later Gateway vacation packages?
Your Gateway getaway should be an escape from your daily routine, not a reason for money-related stress. So to give you extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.