Vacation rentals in Enterprise

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Top-rated vacation rentals in Enterprise

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

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Guest favourite

Cottage in Joseph

4.87 out of 5 average rating, 218 reviews

Charming Mountain View Retreat in Ideal Location

Our bright & charming cottage offers breathtaking mountain views and unparalleled convenience, just 3 blocks from downtown. Indulge in the cozy ambiance by the fireplace or step out onto the perfect deck to soak in the scenery. Your pup will love the fully fenced yard and you will love the well-stocked kitchen and charming touches throughout. Whether you're planning outdoor excursions or seeking a tranquil retreat, Serendipity Cottage is the ideal recreational basecamp for your Joseph adventure.

Jan. 4 – 11

$284 CAD per night

Guest favourite

Guesthouse in Lostine

4.97 out of 5 average rating, 200 reviews

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.

Nov. 16 – 23

$168 CAD per night

Guest favourite

Home in Enterprise

4.95 out of 5 average rating, 56 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.

May 16 – 23

$190 CAD per night

Guest favourite

Guest suite in Cove

4.98 out of 5 average rating, 779 reviews

Almosta Farm Bungalow near La Grande, Sleeps 4

Enjoy stunning sunsets from your private studio bungalow nestled at the base of Mount Fanny in historic Cove, Oregon. Located 10 miles from Union, Oregon and 15 miles from La Grande, Oregon on the Cove-Union Farm Route. We are near mountain biking and hiking & 30 minutes from Moss Spring Trail head (Minam Lodge). We are an hour away from Anthony Lakes and 90 minutes from Jospeh. The studio will sleep up to 4 people if a second bed is requested. Ask about teacher discount. Gay friendly

Mar. 13 – 20

$131 CAD per night

Guest favourite

Yurt in Enterprise

5.0 out of 5 average rating, 54 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!

May 4 – 11

$206 CAD per night

Superhost

Cabin in Joseph

4.88 out of 5 average rating, 43 reviews

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

Nov. 16 – 23

$238 CAD per night

Guest favourite

Guesthouse in Enterprise

4.96 out of 5 average rating, 293 reviews

The Urban Duck, Bungalow living on the pond's edge

The Urban Duck is a cosy, private bungalow nestled on the edge of a large, private duck pond. Find the perfect balance of quiet and seclusion at this idyllic retreat for couples, solos and business travelers alike. Equipped with a kitchenette, refrigerator, bathroom with ensuite rainfall shower, high speed internet, and Roku TV. Outside on the private patio, under the shade of apple trees, is a BBQ, dining area, firepit, and an outdoor clawfoot tub! We are very sorry but NO PETS allowed.

May 25 – Jun. 1

$269 CAD per night

Guest favourite

Apartment in Enterprise

4.89 out of 5 average rating, 130 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.

Apr. 28 – May 5

$166 CAD per night

Guest favourite

Guesthouse in Enterprise

5.0 out of 5 average rating, 8 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 9 laying hens and small 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!

Jan. 3 – 10

$133 CAD per night

Guest favourite

Farm stay in Joseph

4.82 out of 5 average rating, 28 reviews

➗Hideaway

You will be staying on a working ranch with 750 square feet of your own private space. This space is great for a getaway that includes up to six people. It includes two bedrooms, private bath, and open space with futon. The kitchen space is limited. You will have your own entrance and outdoor space allowing you a place to hang out while enjoying the million-dollar view with no extra charge! Our family has been in Wallowa County since 1876 and you will soon see why we are here.

Nov. 14 – 21

$217 CAD per night

Guest favourite

Condo in Joseph

4.93 out of 5 average rating, 135 reviews

Vibrant 2BR Condo Steps from Wallowa Lake Path

Enjoy a vibrant 2BR condo featuring queen beds, a full bathroom, well-equipped kitchen, charming dining area, and inviting lounge with HDTV. Benefit from high-speed WiFi, workspace, pet-friendly policy, and on-site trailer & boat parking. Steps from the Wallowa Lake bike path, this comfortable space is ideal for families, remote workers, and adventurers. Delight in our guests' praise for convenience and excellent communication. Discover Joseph & Wallowa Lake with ease!

Oct. 30 – Nov. 6

$197 CAD per night

Guest favourite

Home in Enterprise

4.89 out of 5 average rating, 73 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. Please private message for details.

Sep. 3 – 10

$499 CAD per night