Holiday rentals in Enterprise
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Quick stats about holiday rentals in Enterprise
Total holiday rentals
Explore 30 holiday rentals in Enterprise
Nightly prices starting at
Enterprise holiday rentals start at £82 per night before taxes and fees
Verified guest reviews
Over 1,990 verified reviews to help you choose
Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 of Enterprise holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Enterprise rentals
4.9 Average rating
Enterprise stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated holiday rentals in Enterprise
Guests agree: these stays are highly rated for location, cleanliness and more.
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.
Popular amenities for Enterprise holiday rentals
Other great holiday rentals in Enterprise
Apt.#4 1908 Ballroom & Stay
Secluded Farmhouse with Stunning Mountain Views
The Little House
The Woodshed - charming 3 bdrm/1 bath bungalow
#06 - Cute cabin w/private Wallowa River access
Bowlby East
First Street Suites "C"
Cheerful 4 bedroom farmhouse with fire pit
Frequently Asked Questions
What are the best places to stay in Enterprise?
Stays around downtown Enterprise are often recommended for easy access to shops and local dining. Rentals near parks or with views of the Wallowa Mountains provide unique surroundings and access to outdoor activities.
What are the best things to do in Enterprise with kids?
Explore local parks for playgrounds and open spaces, visit small museums with hands-on exhibits, or attend seasonal community events. Families often take scenic walks in natural areas and enjoy the town’s friendly atmosphere.
What are some of the best things to do in Enterprise?
Explore regional art galleries, stroll the historic downtown, or enjoy scenic viewpoints in the surrounding area. Many visitors join outdoor adventures like hiking and attend community festivals during warmer seasons.
How is the weather in Enterprise?
Enterprise has chilly winters, often between 30°F and 42°F (-1°C to 6°C), and warm, dry summers that reach around 90°F (32°C). Spring and autumn see milder temperatures and moderate rainfall, so layered clothing is frequently suggested.
When is the best time to visit Enterprise?
Late spring through early autumn is frequently suggested for comfortable temperatures, clear skies, and seasonal festivals. Winter appeals to those who enjoy snow and quieter surroundings.
What are the best places to visit in Enterprise?
Enterprise has galleries featuring regional art, historic sites rooted in local heritage, and scenic parks around town. Many visitors also explore the nearby nature and cultural attractions, such as the Wallowa Mountains and Joseph for art studios.
What are some hiking trails in Enterprise?
Hiking trails around Enterprise include routes through parks, scenic paths in the Wallowa Mountains, and forested tracks near the town. Travelers frequently explore short walks and longer treks for mountain vistas and wildlife viewing.
What are some family activities we can do in Enterprise?
Families often explore local parks with playgrounds, picnic spots, and nature walks. Community events, small museums, and art classes are popular options for children and adults alike.
What are some of the best day trip ideas from Enterprise?
Explore nearby natural areas like the Wallowa Mountains, visit Joseph for art studios and bronze foundries, or enjoy lake activities around Wallowa Lake. Scenic drives and agricultural tours are also popular.
Are there any pet friendly accommodations available in Enterprise?
Many rentals in Enterprise welcome pets, especially in neighborhoods near green spaces and walking trails. Parks and outdoor attractions make it easy to explore with your dog.
What are some local tips for visiting Enterprise?
Locals often recommend dressing in layers for variable mountain weather and bringing sun protection during summer. Many travelers explore locally owned shops around downtown and use Enterprise as a starting point for outdoor adventures in the surrounding area.
What is Enterprise known for?
Enterprise is known for its access to the Wallowa Mountains, regional art scene, and locally rooted heritage. Many travelers appreciate its welcoming community and proximity to outdoor recreation.
What are the best hidden gems to explore in Enterprise?
Enterprise has small galleries, locally rooted coffee shops, and historic buildings often overlooked by visitors. Some travelers discover community gatherings, artisan studios, and lesser known walking paths nearby.
What are the best foods to try in Enterprise?
Enterprise has locally sourced beef, hearty stews, and handmade breads, often featured in restaurants and community markets. Ranch-raised specialties and berry desserts are frequently suggested by residents.
What should I bring for a trip to Enterprise?
Pack layers for shifting mountain temperatures, sturdy shoes for exploring parks or trails, and sun protection for summertime visits. A water bottle, snacks, and a camera are useful for outdoor adventures around Enterprise.
What is the nightlife in Enterprise like?
Enterprise has a laid-back nightlife, centered on local bars, casual eateries, and occasional live music venues. Evening activities often include community gatherings and seasonal performances.
What are the most popular events or festivals in Enterprise?
Enterprise has a county fair with rodeo events, music gatherings, and community markets that highlight regional traditions. These activities are frequently suggested, especially during the warmer months.
Are there family friendly vacation rentals in Enterprise?
Enterprise has family friendly rentals with spacious layouts, kitchens, and nearby recreation. Look for accommodations around the heart of town or in neighborhoods near parks and outdoor spaces.