Holiday rentals in Enterprise

Great Views and Bright, Clean Home in Enterprise!

Incredible view of the valley from our cozy and stylishly updated home in Enterprise! Rest well in new memory foam beds and enjoy your morning coffee from the beautiful window seat. Our home is located in a quiet Enterprise neighborhood, allowing guests to bask in the slow comfort of small-town life. We have Roku TV, high-speed Wi-Fi, and ample parking space. Terminal Gravity Brewing and grocery shopping are a short walk. Our space is off the beaten tourist path, but close enough to everything.

OK Alley, unique historic space, centrally located

Enjoy a relaxing getaway in this one-of-a-kind, unique space, central to nearly all of Enterprise! Once a formerJC Penney's building built in 1910, this apartment was originally the manager's loft. OK Alley shares the alley with the OK Theatre, a historic Theatre built in 1918, that now operates as a musical performance venue/ recording studio. While many of the beautiful, historic details have been preserved, this apartment is spacious and comfortable, with a modern update and a great view!

Ruby Pines Vacation Yurt

Cozy yurt off the beaten path yet close to beautiful Wallowa Lake, the charming town of Joseph, and all the beauty the surrounding Wallowa Mountains have to offer. We are nestled in the pine forests about 5 miles from the towns of Joseph and Enterprise. This space is ideal for a peaceful getaway for a couple, a few friends, or a family with small children. The yurt shares a driveway with the hosts’ primary residence. Please respect the neighborhood and house rules and enjoy your stay!

The Urban Duck Bungalow, Sauna available on reques

The Urban Duck is a cosy, private bungalow nestled on the edge of a large, private duck pond. Find the perfect balance of quiet and seclusion at this idyllic retreat for couples, solos and business travelers alike. Equipped with a kitchenette, refrigerator, bathroom with ensuite rainfall shower, high speed internet, and Roku TV. Outside on the private patio, under the shade of apple trees, is a BBQ, dining area, firepit, and an outdoor clawfoot tub! We are very sorry but NO PETS allowed.

Quiet Clean Home in the Heart of Enterprise

Nestled in a quiet neighborhood this clean 1 bedroom duplex unit provides the perfect home base for your Wallowa County adventures. You'll have complete privacy with all the amenities needed for a short or extended stay. We provide high quality linens, comfortable furniture and walls adorned with local artwork. There have been many upgrades to this retro apartment including a complete kitchen remodel in Spring of 2023. The 2 bedroom unit next door is also available to rent as an Airbnb.

Excellent views, fenced yard, walk everywhere

Our sunny, charming cottage offers awesome mountain views, a cozy fireplace, full kitchen, excellent beds, a perfect deck, and a huge yard for your pup to romp. Only 3 blocks from downtown Joseph and a mile from Wallowa Lake, you will love using Serendipity Cottage as your adventure basecamp in Joseph. We love: --King bed --Awesome mountain views from the deck and front windows --Huge fenced yard --Being walking distance from everything in Joseph --It's quiet! In town, but miles away.

First Street Suites, Main # 12

In the heart of Joseph. Quaint, cozy, apartment type space. One private bedroom with a que bed, living area, full kitchen w/granite counter tops, you can cook or not, step up to cute bathroom with a granite vanity and shower. Walk around the corner to restaurants, galleries & shops. Walking distance to two beautiful parks, lake is within walking distance as well. You will be pleasantly surprised when you open your door. You will not be disappointed.

Lakefront, private dock, hot tub on Wallowa Lake

Delight in a family vacation unlike any other at our exquisite 1,600-square-foot home on the west side of Wallowa Lake. Savor the luxury of private lake access and a seamless private boat dock (*seasonal) during your stay and a private hot tub. Whether you're sipping morning coffee on the deck, grilling with family, or watching the stars from the hot tub, Ponderosa Pines offers the perfect setting for unforgettable summer memories.

Secluded Farmhouse with Stunning Mountain Views

Experience the ultimate getaway at our tranquil farm retreat nestled between Joseph and Enterprise. Enjoy breathtaking mountain views, modern amenities, and cozy interiors perfect for couples or duos. Highlights include a fully equipped kitchen, private location, and the joy of feeding our friendly alpacas and goats. Perfect for nature lovers seeking peace or adventure. Come, stay and create unforgettable memories!