
Eastern Oregon Romantic Holidays
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Top Romantic Eastern Oregon Hotels

Beautifully renovated 1920's Bungalow with a large fenced yard in Enterprise, OR
Enterprise
Book a stay at this family-friendly vacation home in Enterprise. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Enterprise Public Library ...
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

The Wild Iris House
Joseph
Book a stay at this family-friendly vacation home in Joseph. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wallowa Lake and Wallowa ...
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

Turn Of The Century Charm - Walk to Town DISCOUNTS FOR SKIING?
Baker City
Stay at this vacation home in Baker City. Enjoy free WiFi, 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
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.