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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.

Joseph Cottage: Mountain Views, Fireplace, Firepit

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!

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!

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

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 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, rabbits 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!

Charming cabin! Spacious parking,3 beds, 1 bedroom

This cabin’s convenient location offers the comforts of town and is within walking distance to brewery and down town. It is also only a short drive to Joseph and Wallowa Lake. This clean, cozy environment provides a peaceful place to relax between adventures. Cautiously enjoy the creek in the backyard. Bring the boat, there is plenty of parking. Pet Policy- Thanks to considerate pet parents. Well behaved pet are welcome. Please keep pets off furniture. Please clean up after them outside

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.

Large 2 BR in Historic Litch Hotel | Aneroid Unit

Stay at Aneroid, a luxurious condo in the historic Litch Hotel, combining modern comforts with vintage charm. Enjoy soaring 15ft ceilings, hardwood floors, stone walls, quartz countertops, and handcrafted Olaf dishware. The bathroom includes a makeup station for added convenience. Main floor: king bed; mezzanine: king bed. Pet-friendly! Located minutes from Joseph and Wallowa Lake, guests rave about our top-notch communication, detailed guidebook, and seamless self check-in.

Serene Japanese Home with Million $ View in Oregon

Welcome to 'Zen House Kominka,' where historical charm meets modern luxury. Our home features repurposed timbers and beams from traditional Japanese farmhouses, some over 200 years old, preserved to honor Japan's ancient craftsmanship. Enjoy tranquility amidst breathtaking mountain vistas. Zen House Kominka offers a serene escape, connecting you with Japan's rich heritage and northeast Oregon's dynamic natural beauty. Unfortunately, children under 18 are not allowed.

Enterprise Guest House

Centrally located in downtown Enterprise & 7 scenic miles to Wallowa Lake, this historic gem boasts three upstairs guest rooms, each with en suite bathrooms. Large kitchen is great for group meals and morning coffee. Cozy up in the sunny dining room or living room and play a few tunes on the piano. Stone’s throw to coffee, groceries, pubs and live music. Pendleton bedding, organic cotton sheets, and new gel memory foam mattresses make for a great night’s sleep.

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.