Vacation rentals in Enterprise

4.97 out of 5 average rating, 246 reviews

A private outdoor patio is presented, featuring two red chairs and a small round table, adorned with two glasses. Soft lighting is strung overhead, enhancing the serene atmosphere. Surrounding trees and a mountain view are visible in the background during dusk.

Guesthouse in Lostine

Barn Studio with King Bed & No Extra Fees!

Our newer space is great for groups of 3 or less. We don't charge a cleaning fee or per person fee! Great location for hiking, riding the Eagle Cap Excursion Train, pedaling the Joseph Branch Rail Riders, rafting the river or enjoying Wallowa Lake which is also close by. We live in the front of the barn house, the studio is it's own private space with a full kitchen, washer & dryer and private outdoor space. Excellent WiFi, super clean, quiet and comfortable place in beautiful Wallowa County.

4.95 out of 5 average rating, 83 reviews

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

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.

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

4.78 out of 5 average rating, 54 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 Terminal Gravity Brewery. 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

4.98 out of 5 average rating, 102 reviews

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

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!

Superhost

An aerial view of the tiny home showcases two sleeping areas, with a loft bed visible above. The kitchen area contains a gas stove and a small dining table. Large windows provide natural light, and colorful artwork adorns the walls, enhancing the bright interior.

Tiny home in Joseph

5 out of 5 average rating, 4 reviews

Charming BoHo Tiny Home w/ MEGA Mt Views!

Experience our darling custom built tiny home w/ HUGE mountain views in a private setting close to the Joseph airport and walkable to the town of Joseph. With its mt vistas & easy access you won’t want to leave. Sunsets & night stargazing are amazing too! Carefully curated, our home is fully equipped with everything you need, including spa quality linens & fully equipped kitchen. It boasts original art pieces, big windows & plenty of sunshine along w/ fun, bright & cheery furnishings.

Guest suite in Enterprise

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.

4.91 out of 5 average rating, 77 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!

4.92 out of 5 average rating, 75 reviews

A modern chalet is elevated on stilts, surrounded by lush green trees. A wooden deck extends from the building, leading to a stone pathway. Steps ascend the slope, providing access to the structure, which features large windows that invite natural light.

Cabin in Joseph

Best views at Wallowa Lake- Chalet North

The Wallowa Lake Chalets are situated between Wallowa Lake and the Eagle Cap Wilderness. The 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

4.88 out of 5 average rating, 167 reviews

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

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.

4.92 out of 5 average rating, 12 reviews

An inviting living area features a plush blue couch with decorative pillows, positioned near an open door that frames stunning mountain views. A library ladder leads to a lofted sleeping area, while a small wooden table is situated nearby.

Cabin in Joseph

All New! Remodeled Tiny Cabin in Downtown Joseph

EVERYTHING IS NEW! From the fixtures to the furnishings, everything inside this tiny log cabin is new, stylish, and completely cozy. You'll love the amazing mountain views, cozy fireplace, gorgeous furniture, and being steps from the best restaurants, shops, and galleries in downtown Joseph. The McCully Cabin was originally built and housed on a historic ranch. Recently relocated to its current location in downtown Joseph, it was completely remodeled in 2025 and is waiting to host you.

5 out of 5 average rating, 31 reviews

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

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.

4.89 out of 5 average rating, 102 reviews

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

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. Please private message for details.

4.78 out of 5 average rating, 143 reviews

The entrance features a bright yellow door framed by a decorative sign reading 'First Street Suites.' Hanging flower baskets filled with vibrant red flowers adorn the exterior, complemented by potted plants with colorful blooms at the base. A simple, welcoming façade presents a cozy appeal.

Condo in Joseph

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.

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Popular amenities for Enterprise vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Enterprise

4.93 out of 5 average rating, 127 reviews

A spacious living area is furnished with a tan leather sofa adorned with various decorative cushions. A wooden dining table for four is positioned nearby, while a fully equipped kitchen is visible in the background. Light floods the space through large windows, enhancing the welcoming atmosphere.

Condo in Joseph

Vibrant 2BR Condo by Wallowa Lake Bike Path

Superhost

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

4.93 out of 5 average rating, 45 reviews

Bowlby East Studio (Apt #2)

A spacious living area features wood floors and various framed photographs on the walls. A comfortable leather sofa and a light-colored coffee table are centered in the room, complemented by a geometric patterned rug. A dining table for four is visible, along with modern kitchen appliances.

5 out of 5 average rating, 22 reviews

2 BR 2nd FL Litch Hotel | Nez Perce Theme

5 out of 5 average rating, 46 reviews

A cozy living area showcases exposed stone walls and large windows that allow natural light to fill the space. Two comfortable sofas, one in brown leather and another in a lighter shade, are positioned near a wooden side table and a television, enhancing the inviting atmosphere.

Apartment in Enterprise

Barber Shop

Private room in Enterprise

4.91 out of 5 average rating, 22 reviews

Enterprise Guest House Room #3

The kitchen is equipped with new appliances and quartz countertops. Open shelving displays various kitchen essentials and spices. A toaster and coffee maker are visible, alongside a dark stove and refrigerator. The warm wood flooring complements the textured stone wall, enhancing the modern aesthetic.

5 out of 5 average rating, 59 reviews

Drug Store Themed Unit | Historic LItch Hotel

The kitchen area showcases modern appliances set against dark cabinetry and light countertops. Natural wood flooring extends throughout the space, complemented by a unique wall decoration featuring rustic elements. Large windows invite natural light and provide a glimpse of the outdoor scenery.

4.93 out of 5 average rating, 71 reviews

Rodeo themed unit - Historic Litch Hotel

A spacious bedroom features a cozy king bed enclosed within a camping-inspired canvas tent structure. Soft lighting illuminates the interior, while a stone wall adds a rustic touch, contributing to the unique design of the space.