Holiday houses in Wallowa County

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.

Value · Location · View

Serene Japanese Home with Million $ View in Oregon

Featured in The New York Times. One of only a few authentic 100-year-old Japanese farmhouses (kominka) outside Japan. It's constructed with original timbers, some more than 200 years old, carefully preserved to honor Japan’s ancient craftsmanship. Comparable ones, like the Shoya House at The Huntington Library in CA, exist as museums. Here, you can live in one. Enjoy Japan’s rich architectural heritage and the dynamic natural beauty of Northeast Oregon. Please note: Guests must be 18 or older.

Family · Location · Condition

Best views at Wallowa Lake- Chalet South

The Wallowa Lake Chalets are situated between Wallowa Lake and the Eagle Cap Wilderness. These Chalets have an open floor plan and were designed to encapsulate the natural surrounding beauty. The decks of the Chalets stand 26 ft above the ground creating some of the most surreal views that can be found anywhere in Wallowa County. The Chalets can be accessed by a ½ mile of rugged gravel road off of Wallowa Lake Hwy. The Chalets are about 8 min. from Joseph, OR. Follow us @wallowa_lake_chalets

Value · Location · Beach

Serendipity Cottage | Mtn Views + Walk to Downtown

Wake up to sweeping Wallowa Mountain views, sip coffee on the sunny deck, and unwind by the fire under star-filled skies. Just 3 blocks from downtown and minutes to Wallowa Lake, this charming cottage is the perfect home base for your Joseph getaway. Designed for comfort and connection, Serendipity Cottage offers a cozy fireplace, a fully equipped kitchen, and a spacious fenced yard—perfect for relaxing after a day of hiking, exploring, or lake adventures. You and your pup will love it here!

Family · Value · Decor

Almosta Farm Bungalow near La Grande, Sleeps 4

Enjoy stunning sunsets from your private studio bungalow nestled at the base of Mount Fanny in historic Cove, Oregon. Located 10 miles from Union, Oregon and 15 miles from La Grande, Oregon on the Cove-Union Farm Route. We are near mountain biking and hiking & 30 minutes from Moss Spring Trail head (Minam Lodge). We are an hour away from Anthony Lakes and 90 minutes from Jospeh. The studio will sleep up to 4 people if a second bed is requested. Ask about teacher discount. Gay friendly

Location · Family · Cleanliness

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!

Family · Value · Kitchen

#52-Wallowa Lakefront beautiful home w/lake access

Wallowa Lake is one of our favorite places to vacation with our kids and grandkids! We’ve spent countless valuable hours here and we are excited to share our favorite place with you and your family! Our home is comfortable for people of all ages. We bring our parents here and love that they have complete enjoyment of the full space inside and outside. They can sit on the deck & enjoy the family playing in the lake and get to be a part of the memories our kids and grandkids are making!

Family · Location · Check-in

The Park Street Farm-ette

Quaint private studio with patio. Walking distance to downtown Enterprise as well as Ant Flat 'scenic area.' Homeowners have 25 laying hens and garden. Private entrance, driveway parking and patio with dining area. Enjoy morning coffee with the early sun, or evening drinks in the shade. Coffee, lunch, and dinner less than 10 minutes walk away, and about 10 miles from Wallowa Lake. We invite you to come stay in our cute country studio and enjoy the perks of slower, rural life!

Value · Family · Quiet

Log cabin in Troy, OR (not in Enterprise)

$200 per night for the month of September '26. changes to $300 per night October, November. This Troy, OR log cabin (not in Enterprise) is located West down Bartlett Road, past the row of mailboxes on your left, and forward. The cabin has two bedrooms (one upstairs in the loft), a kitchen, laundry, porch, and outdoor space for tents, games, kids and dogs. Private access to the Wenaha River is behind the cabin. The Grande Ronde River is also a short walk away.

Value · Family · Nearby

#26-Cozy home in the pines @ resortside Wallowa Lk

Tucked off the road the driveway is easy to miss which is our favorite part of the home! Situated among the trees, on a little stream, private and relaxing are two words often used to describe our cabin! This home is perfect for the adventurers, the small families, the reconnecting couples! Close enough to walk to the resort side activities at Wallowa Lake but tucked back for privacy, relaxation and enjoyment of being in the woods!

Family · Location · Accuracy

River Street Escape

Welcome to your ideal Enterprise, Oregon vacation rental—a cheerful and comfortable home base for adventure in Wallowa County. Perfect for families and groups, this cozy getaway offers all the comforts of home while putting you close to hiking, fishing, skiing, and the best of Enterprise and Joseph, Oregon. Relax, recharge, and enjoy easy access to outdoor recreation, local dining, and small-town charm.

Family · Location · Cleanliness

Blue Mountain Getaway

Relax with the whole family at this cozy 2 bedroom home. Everything you need for a peaceful getaway is provided. Kid friendly with a fenced back yard and quiet neighbors. Small breed dogs allowed - please check with us for larger breeds before booking. Sleeping accommodations include: Queen bed, Twin/Full bunk bed, Rollaway bed, a couch, a queen size air mattress, and a futon.

Location · Value · Barbecue