Vacation rentals in Enterprise

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Top-rated vacation rentals in Enterprise

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

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Guest favorite

Cottage in Joseph

4.87 out of 5 average rating, 219 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.

Mar 3 – 10

ﺩ.ﺇ1,001 per night

Guest favorite

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 11 – 18

ﺩ.ﺇ441 per night

Guest favorite

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.

Sep 6 – 13

ﺩ.ﺇ493 per night

Superhost

Cabin in Joseph

4.91 out of 5 average rating, 43 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

Nov 24 – Dec 1

ﺩ.ﺇ573 per night

Guest favorite

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

ﺩ.ﺇ526 per night

Guest favorite

Home in Joseph

5.0 out of 5 average rating, 35 reviews

Creekside, Great Views, In Heart of Downtown

The Red Horse Retreat in downtown Joseph was once a a local's favorite cafe and coffee shop that has since been transformed into a bright and charming vacation home in the heart of downtown Joseph. The Red Horse now features two large living areas, expansive decks next to the creek with great views of the Wallowa Mountains , an "almost full" kitchen, and sleeping for six guests with a king, queen and double bed. You'll love the bright spaces, the charming touches, and the awesome location.

May 6 – 13

ﺩ.ﺇ762 per night

Guest favorite

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.

Aug 6 – 13

ﺩ.ﺇ771 per night

Guest favorite

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.

May 13 – 20

ﺩ.ﺇ432 per night

Guest favorite

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!

Oct 15 – 22

ﺩ.ﺇ295 per night

Guest favorite

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.

May 11 – 18

ﺩ.ﺇ532 per night

Guest favorite

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!

Apr 1 – 8

ﺩ.ﺇ475 per night

Guest favorite

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.

May 4 – 11

ﺩ.ﺇ1,264 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Enterprise vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Enterprise's top sights

Terminal Gravity Brewery & Pub24 locals recommend

Safeway5 locals recommend

La Laguna Family Mexican Restaurant5 locals recommend

Red Rooster Cafe5 locals recommend

Range Rider8 locals recommend

Wild Carrot Herbals3 locals recommend

Other great vacation rentals in Enterprise

Guest favorite

Apartment in Joseph

4.92 out of 5 average rating, 90 reviews

First Street Suites #5

Jan 28 – Feb 4

ﺩ.ﺇ591 per night

Guest favorite

Home in Joseph

5.0 out of 5 average rating, 10 reviews

Quiet Retreat with Wallowa Lake & Mountain Views!

May 7 – 14

ﺩ.ﺇ1,792 per night

Guest favorite

Condo in Joseph

4.94 out of 5 average rating, 85 reviews

Heart of Joseph. Very Private and Cozy.

Mar 21 – 28

ﺩ.ﺇ612 per night

Superhost

Cabin in Joseph

4.78 out of 5 average rating, 37 reviews

The Cottage

Oct 25 – Nov 1

ﺩ.ﺇ723 per night

Superhost

Loft in Enterprise

5.0 out of 5 average rating, 16 reviews

OK Alley, unique historic space, centrally located

Jul 17 – 24

ﺩ.ﺇ1,025 per night

Guest favorite

Vacation home in Joseph

4.93 out of 5 average rating, 14 reviews

Stunning Lake House with private dock

May 9 – 16

ﺩ.ﺇ1,666 per night

Guest favorite

Cabin in Joseph

4.91 out of 5 average rating, 66 reviews

Newer Stunning Log Cabin Tucked in the Pines

Oct 12 – 19

ﺩ.ﺇ787 per night

Guest favorite

Home in Joseph

4.97 out of 5 average rating, 79 reviews

Family friendly, close to the State Park

Sep 12 – 19

ﺩ.ﺇ1,005 per night

Show all

Other great vacation rentals in Enterprise

Guest favorite

Condo in Enterprise

5.0 out of 5 average rating, 68 reviews

Spacious 2 BR in Historic Building | Aneroid Unit

Apr 23 – 30

ﺩ.ﺇ537 per night

Guest favorite

Condo in Joseph

4.96 out of 5 average rating, 27 reviews

Cozy 2BR Condo Steps from Wallowa Lake Path

Dec 7 – 14

ﺩ.ﺇ484 per night

Guest favorite

Condo in Joseph

4.97 out of 5 average rating, 63 reviews

Modern, Stylish Condo Near W. Lake & DTWN Joseph

Mar 22 – 29

ﺩ.ﺇ498 per night

Guest favorite

Home in Joseph

4.99 out of 5 average rating, 73 reviews

Secluded Farmhouse with Stunning Mountain Views

Dec 14 – 21

ﺩ.ﺇ1,032 per night

Guest favorite

Condo in Enterprise

5.0 out of 5 average rating, 17 reviews

Drug Store Themed Unit | Historic LItch Hotel

Oct 9 – 16

ﺩ.ﺇ659 per night

Guest favorite

Condo in Joseph

4.89 out of 5 average rating, 45 reviews

Cute Condo perfect for 1 - 4 guests

Sep 4 – 11

ﺩ.ﺇ511 per night

Guest favorite

Condo in Enterprise

4.95 out of 5 average rating, 55 reviews

Luxury Sacajawea Condo, Heart of Wallowa County

Nov 30 – Dec 7

ﺩ.ﺇ692 per night

Guest favorite

Home in Joseph

5.0 out of 5 average rating, 39 reviews

Beautiful new home at Wallowa Lake with dock.

Feb 27 – Mar 6

ﺩ.ﺇ1,406 per night

Show all

Quick stats about vacation rentals in Enterprise

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.1K reviews
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Enterprise?
Yes! Work meets play with ease at over 20 vacation rentals in Enterprise featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Enterprise?
Experience the best of Enterprise with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Enterprise?
Four-legged friends are welcome in Enterprise. Choose from more than 10 vacation rentals for guests traveling with pets.
Do apartment rentals in Enterprise have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Enterprise. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Enterprise

Top-rated vacation rentals in Enterprise

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Enterprise vacation rentals

Stay near Enterprise's top sights

Other great vacation rentals in Enterprise

Apartment in Joseph

Home in Joseph

Condo in Joseph

Cabin in Joseph

Loft in Enterprise

Vacation home in Joseph

Cabin in Joseph

Home in Joseph

Other great vacation rentals in Enterprise

Condo in Enterprise

Condo in Joseph

Condo in Joseph

Home in Joseph

Condo in Enterprise

Condo in Joseph

Condo in Enterprise

Home in Joseph

Quick stats about vacation rentals in Enterprise

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Enterprise?

How much does it cost to stay in apartment rentals in Enterprise?

Are there pet-friendly vacation rentals in Enterprise?

Do apartment rentals in Enterprise have wifi?

Destinations to explore