Eastern Oregon Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

Photo by Joe Kubitschek
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How to find a romantic Eastern Oregon holiday

How can I find the best Eastern Oregon vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Eastern Oregon. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Eastern Oregon romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Eastern Oregon that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Eastern Oregon romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Eastern Oregon?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Eastern Oregon?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Eastern Oregon that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Eastern Oregon with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Eastern Oregon romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Eastern Oregon Hotels

Beautifully renovated 1920's Bungalow with a large fenced yard in Enterprise, OR
Beautifully renovated 1920's Bungalow with a large fenced yard in Enterprise, OR
Enterprise, OR
  • 20 min drive from Wallowa Lake
Stay at this family-friendly holiday home in Enterprise. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Enterprise Public Library and ...
9.8/10 Exceptional! (130 reviews)
Like coming home.
"This was a perfect place for our Christmas stay with friends in Enterprise. We had our own cozy place to come back too each night after hanging out with friends and family over the holidays. We loved how warm and inviting it was and really appreciated that they had a tree up and decorated for the ..."

Reviewed on 6 Jan 2025

Beautifully renovated 1920's Bungalow with a large fenced yard in Enterprise, OR
 The Wild Iris House
The Wild Iris House
Joseph, OR
  • 6 min drive from Wallowa Lake
Stay at this family-friendly holiday home in Joseph. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wallowa Lake and Wallowa County Museum ...
10/10 Exceptional! (166 reviews)
Cozy stay in a great location!
"We had a great stay in the Wild Iris House. Set against a beautifully mountain backdrop, it is located right on the edge of downtown Joseph and within walking distance of virtually all the best shops and eateries in town. Each day of our stay, we had unexpected visits from wildlife, including a six-point ..."

Reviewed on 2 Jul 2025

The Wild Iris House
Turn Of The Century Charm  - Walk to Town       DISCOUNTS FOR SKIING?
Turn Of The Century Charm - Walk to Town DISCOUNTS FOR SKIING?
Baker City, OR
  • 2 hours drive from Wallowa Lake
Stay at this holiday home in Baker City. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Crossroads Carnegie Art Center and Baker City ...
9.6/10 Exceptional! (68 reviews)
Spacious, Comfortable place for a weekend stay
"The home was comfortable and spacious. We had 6 adults sharing the space for a weekend to attend a local gathering. The beds were comfortable. Everything was clean and the space was welcoming. We enjoyed the nature and landscape photographs decorating the rooms throughout."

Reviewed on 9 May 2025

Turn Of The Century Charm - Walk to Town DISCOUNTS FOR SKIING?
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.

More holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.