Vacation rentals in Enterprise

4.97 out of 5 average rating, 243 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.

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.

4.95 out of 5 average rating, 81 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.

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

4.79 out of 5 average rating, 48 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

Superhost

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, 99 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 new 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. After Check-in 3 % Joseph, 5% Wallowa County Lodging tax, Airbnb request sent.

4.98 out of 5 average rating, 95 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!

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.

4.92 out of 5 average rating, 71 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!

4.88 out of 5 average rating, 162 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.

4.88 out of 5 average rating, 238 reviews

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

Excellent views, fenced yard, walk everywhere

Our sunny, charming cottage offers awesome mountain views, a cozy fireplace, full kitchen, excellent beds, a perfect deck, and a huge yard for your pup to romp. Only 3 blocks from downtown Joseph and a mile from Wallowa Lake, you will love using Serendipity Cottage as your adventure basecamp in Joseph. We love: --King bed --Awesome mountain views from the deck and front windows --Huge fenced yard --Being walking distance from everything in Joseph --It's quiet! In town, but miles away.

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.

5 out of 5 average rating, 22 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.

4.78 out of 5 average rating, 139 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.

Superhost

A spacious living room displays a comfortable arrangement of brown sofas and accent stools. A wall-mounted television is positioned across from a cozy gas fireplace, framed by a textured wood backdrop. Natural light filters in through large windows, enhancing the inviting space.

4.72 out of 5 average rating, 18 reviews

Comfortable 3BR Home - Convenient Location!

River St Retreat is a wonderful 3 Bedroom 1 Bathroom home with all the amenities! Large Living room, kitchen and private backyard space! Backyard is not fully fenced but very private! Travelling for work or play this home is centrally located in Enterprise, 3 blocks from the courthouse and 5 minutes to Wallowa Memorial! And walking distance to all of downtown Enterprise restaurants and business. 10 minute drive to Joseph and Wallowa Lake!

5 out of 5 average rating, 12 reviews

A spacious living area features vaulted wood ceilings and triangular windows, allowing ample natural light. A cozy sofa and armchair surround a circular area rug. A dining table is set with fresh fruit, and a wood-burning stove is positioned near the window.

Cabin in Joseph

Lakefront, private dock, hot tub on Wallowa Lake

Delight in a family vacation unlike any other at our exquisite 1,600-square-foot home on the west side of Wallowa Lake. Savor the luxury of private lake access and a seamless private boat dock (*seasonal) during your stay and a private hot tub. Whether you're sipping morning coffee on the deck, grilling with family, or watching the stars from the hot tub, Ponderosa Pines offers the perfect setting for unforgettable summer memories.

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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

4.89 out of 5 average rating, 47 reviews

A spacious living area features a comfortable brown leather couch and an armchair, set around a wooden coffee table. Natural light enters through a large window with a view of the outdoors, and a woven area rug complements the warm wooden flooring.

Apartment in Enterprise

Bowlby West Studio (Apt #3)

4.93 out of 5 average rating, 125 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

A bright and airy room features three tall windows that allow natural light to fill the space. A spacious bed is complemented by a wooden writing desk and a comfortable couch. A decorative area rug adds warmth to the hardwood floor.

Hotel room in Joseph

4.93 out of 5 average rating, 107 reviews

Room #4 Book Direct & Save—JenningsHotel(.)com

The living area features hardwood flooring with a large area rug at the center. A dark brown sofa is positioned adjacent to a wall-mounted television, complemented by decorative shelves displaying various items. Natural light filters through large windows, illuminating the open space.

4.93 out of 5 average rating, 45 reviews

Wallowa Mountains Retreat minutes to Joseph, OR

A distinctive entrance features a large arched window with the word 'Ballroom' elegantly displayed above a dark door. Flanking the entrance are two large planters filled with vibrant flowers, and a welcome mat is placed on the ground.

Hotel room in Enterprise

5 out of 5 average rating, 4 reviews

Room #6 1908 Ballroom & Stay

5 out of 5 average rating, 40 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

4.88 out of 5 average rating, 17 reviews

Enterprise Guest House Room #3