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Holiday houses in Enterprise

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Top-rated holiday rentals in Enterprise

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A cozy living area features a dark couch adorned with decorative cushions, paired with two green ottomans. A light rug lies on the floor, while large windows with plantation shutters allow natural light to fill the space. Wall art and a clock add subtle decorations.
Home in Enterprise
4.96 out of 5 average rating, 94 reviews

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.

Top Guest favourite
A charming cottage is set against a blue sky, featuring a well-maintained lawn and landscaped garden. A pathway leads to the entrance, which is framed by light-colored shutters and a blue front door. A deck is visible to the left, adding to the inviting exterior.
Cottage in Joseph
4.89 out of 5 average rating, 253 reviews

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!

Guest favourite
A well-lit entryway features a staircase leading to the upper level. The walls showcase preserved historic details. The spacious room on the lower level is captured with wooden flooring and a few simple furnishings, including a table and chairs, creating an open atmosphere.
Loft in Enterprise
4.95 out of 5 average rating, 39 reviews

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!

Guest favourite
The modern chalet is elevated on sturdy stilts, surrounded by lush greenery. The exterior features large windows and a wooden deck, providing access to the fresh mountain air and spectacular wooded views. The structure blends naturally with its forested environment.
Cabin in Joseph
4.91 out of 5 average rating, 129 reviews

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

Top Guest favourite
A cozy yurt is surrounded by tall pine trees, featuring a wooden deck with steps leading up to the entrance. A picnic table is positioned nearby on a gravel area, providing an outdoor space for relaxation.
Yurt in Enterprise
4.98 out of 5 average rating, 119 reviews

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!

Guest favourite
A cozy studio space features a spacious bed with a decorative blue pillow and light-colored bedding. Two small wooden chairs surround a compact table, while natural light filters through a window with blue curtains.
Guest suite in Enterprise
4.92 out of 5 average rating, 110 reviews

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!

Superhost
An inviting living area features a comfortable brown couch and a light-colored armchair. A wooden wall display includes a bear photo, while a flat-screen TV is mounted above a stylish gray cabinet. A compact kitchenette with modern appliances is visible in the background.
Cabin in Enterprise
4.8 out of 5 average rating, 65 reviews

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

Guest favourite
A bright and open living space features a modern kitchen with wooden cabinetry and stainless steel appliances. A wooden dining table is positioned next to a large window that provides natural light, while a comfortable chair is located near the entrance.
Apartment in Enterprise
4.88 out of 5 average rating, 173 reviews

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.

Guest favourite
An aerial view of a rustic venue surrounded by tall pine trees and expansive green fields. The event space is set with rows of white chairs facing a building, framed by snow-capped mountains in the background under a partly cloudy sky.
Home in Enterprise
4.89 out of 5 average rating, 109 reviews

Cheerful 4 bedroom farmhouse with fire pit

Jones Farmhouse is located on a working farm that has been in our family for 40 years. Comfy and spacious this unique listing will give you great family trip memories. The front deck mountain views are hard to beat, and will create cozy and fun times. Jones Farmhouse is located 3 miles from Enterprise and 3 miles from Joseph on a quiet country road. Backyard venue available for up to 100 people for additional cost. {Weddings possible) Please private message for details.

Top Guest favourite
A modern house is set against a backdrop of snow-capped mountains, surrounded by greenery. The clear blue sky complements the serene landscape, highlighting the home's elevated position amidst the natural beauty.
Home in Enterprise
5 out of 5 average rating, 48 reviews

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.

Guest favourite
A functional kitchen area features wooden cabinets and granite countertops, accompanied by a spacious island with seating for four. A black refrigerator sits adjacent to a doorway leading to a bedroom. A cozy living room with a dark sofa is visible in the background.
Condo in Joseph
4.93 out of 5 average rating, 111 reviews

Heart of Joseph. Very Private and Cozy.

This amazing Suite is very private with all the COZY amenities that makes it a home. Summer 3 nights minimum. Get a great night sleep in the great King size luxury bed in Master Bedroom, unpack stay awhile, Wardrobe closet can accommodate cloths to hang or fold . Living room converts instantly into a second sleeping room & dresser with a comfortable queen murphy bed already made with super soft sheets and comforter.

Top Guest favourite
An expansive view showcases the farm's greenery, barn, and mountains in the background. Large windows in the cozy lounge area reveal abundant natural light, while the king bedroom above features a serene decor and ample space, adding to the retreat's comfort.
Home in Joseph
4.97 out of 5 average rating, 165 reviews

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!

Popular amenities for Enterprise holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Enterprise

Guest favourite
A spacious home with a wood exterior and green roof is situated against the backdrop of the Wallowa Mountains. The property features a large driveway leading to a three-car garage, surrounded by grassy areas and a few trees.
Home in Joseph
4.88 out of 5 average rating, 59 reviews

Spacious Farmhouse with Stunning Mountain Views

Guest favourite
The entrance features a tall arched door with decorative glass labeled 'Ballroom.' Flanking the door are large planters filled with colorful flowers. A welcome mat lies on the ground, enhancing the inviting aspect of the entryway.
Apartment in Enterprise
5 out of 5 average rating, 9 reviews

Apt.#4 1908 Ballroom & Stay

Top Guest favourite
A cozy white house with a green metal roof is surrounded by lush trees and greenery. Large windows provide natural light, and seating areas are visible on the porch. The exterior reflects a serene rural setting.
Farm stay in Wallowa
4.96 out of 5 average rating, 71 reviews

The Little House

The living room features two green armchairs adorned with decorative pillows, positioned near a wooden coffee table. A vintage upright piano is visible in the background, accompanied by a cozy atmosphere created by warm wood paneling and soft lighting.
Home in Enterprise
4.61 out of 5 average rating, 85 reviews

The Woodshed - charming 3 bdrm/1 bath bungalow

A spacious deck features a large umbrella providing shade over two reclining chairs, positioned to overlook a landscaped area. Mountain views are visible in the background, and the wooden deck offers ample space for relaxation.
Casa particular in Enterprise
4.7 out of 5 average rating, 20 reviews

NEO CASA Quiet residential spot

Guest favourite
A light-filled living area features large windows with soft white curtains, a comfortable brown leather sofa, and a matching armchair. A wooden coffee table sits on a decorative rug, while a wall-mounted television adds functionality. Natural wood flooring complements the minimalist decor.
Apartment in Enterprise
4.94 out of 5 average rating, 49 reviews

Bowlby East

The living area features a comfortable seating arrangement with a wall-mounted TV and large windows allowing natural light. A round dining table is set for four, and a decorative rug adds warmth to the hardwood floors. Staircase details are visible in the background.
Condo in Joseph
4.75 out of 5 average rating, 85 reviews

Walkable Studio Wallowa Lake | Dog Friendly

Guest favourite
A historic house exterior is showcased under clear blue skies. The structure features wooden shingle siding and a welcoming porch, bordered by green grass. Trees provide shade, and a black dog stands in the foreground, highlighting a tranquil outdoor setting.
Home in Enterprise
5 out of 5 average rating, 7 reviews

Enterprise Guest House

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.

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 $101 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,890 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Enterprise holiday rentals include Wi-Fi 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!

  1. Airbnb
  2. United States
  3. Oregon
  4. Wallowa County
  5. Enterprise