Enterprise vacation rentals

We found 82 vacation rentals — enter your dates for availability

Nestled in the heart of the breathtaking Wallowa Mountains, Enterprise is a paradise for outdoor enthusiasts and families alike. With its charming downtown brimming with friendly faces and unique shops, this inviting destination offers endless adventures, from hiking scenic trails to exploring picturesque lakes. Choose from cozy vacation rentals—private homes, condos, and charming cottages—where you can unwind and create lasting memories, all while enjoying the comfort and convenience of a home-away-from-home experience.

Holiday rentals with weekly discounts - Enterprise

Showing deals for:Jan 15 - Jan 22

Living area
Outdoor dining
Bedroom view looking south - wake to this!
Interior
Exceptional
(81 reviews)

3 Bedroom Farm Home. Sleeps 10 - One Mile Outside Joseph, Oregon. The Evans Farm

Joseph

9% off
$422
$2,952 for 7 nights
All fees included
3 Bedroom Farm Home. Sleeps 10 - One Mile Outside Joseph, Oregon. The Evans Farm
Exterior
Outdoor dining
Interior
Interior
Exceptional
(9 reviews)

Golden Saddle lakefront log home-Wallowa Lake

Enterprise

8% off
$703
$4,918 for 7 nights
All fees included
Golden Saddle lakefront log home-Wallowa Lake
Living area
Exterior
Private kitchen
Interior
Exceptional
(5 reviews)

Mountain View Townhome A |Walk to Downtown Joseph

Joseph

8% off
$200
$1,402 for 7 nights
All fees included
Mountain View Townhome A |Walk to Downtown Joseph
Private kitchen
Living area
Living area
Exterior detail
Exceptional
(90 reviews)

Joseph Cottage: Mountain Views + Fireplace + Firepit

Joseph

8% off
$240
$1,677 for 7 nights
All fees included
Joseph Cottage: Mountain Views + Fireplace + Firepit
New heated stargazing dome steps away from the cabin. So incredible!
New, beautiful cabin with fabulous views!
Terrace/patio
Private yet close to amenities.
Exceptional
(13 reviews)

Juniper Cabin. Private cabin with majestic views and clear stargazing dome!

Enterprise

8% off
$197
$1,381 for 7 nights
All fees included
Juniper Cabin. Private cabin with majestic views and clear stargazing dome!
Outdoor dining
Living area
Interior
Private kitchen
Exceptional
(23 reviews)

Blue Moon Retreat ~~ Spacious duplex unit with SAUNA and a stunning view

Joseph

12% off
$205
$1,438 for 7 nights
All fees included
Blue Moon Retreat ~~ Spacious duplex unit with SAUNA and a stunning view
Living area
Private kitchen
Interior
Living area
Exceptional
(5 reviews)

Mountain View Townhome E| Walk to Downtown Joseph

Joseph

8% off
$218
$1,529 for 7 nights
All fees included
Mountain View Townhome E| Walk to Downtown Joseph

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Find out more about Enterprise

Why visit Enterprise

  • Outdoor Adventures: Enterprise is a haven for outdoor enthusiasts, featuring nearby state parks perfect for hiking and exploring breathtaking scenery.
  • Picturesque Downtown: Stroll through the charming downtown area filled with friendly locals, unique shops, and a warm atmosphere.
  • Family-Friendly Vibe: The welcoming environment in Enterprise makes it an ideal destination for families seeking fun activities and memorable experiences.
  • Cozy Accommodations: Enjoy a variety of comfortable vacation rentals, including private homes, condos, and charming cottages.
  • Local Culture: Experience the rich culture of Enterprise through its libraries, parks, and community events.

Popular types of accommodation in Enterprise

When it comes to vacation rentals in Enterprise, you'll find a variety of cozy options to suit your needs, including houses, condos, and charming cottages. Whether you're seeking an extended stay or a quick getaway, these accommodations offer essential amenities to make your trip comfortable. Explore your choices and discover the perfect spot for relaxation and adventure in Enterprise.

  • Houses: The top choice for many visitors to Enterprise, offering spacious and comfortable accommodations for families or groups.
  • Condos: A popular option for those seeking modern amenities and convenience, perfect for a relaxing getaway.
  • Cottages: Ideal for a quaint and cozy experience, these charming retreats are nestled in nature.
  • Cabins: A favorite among outdoor enthusiasts, providing a rustic atmosphere and access to beautiful landscapes.
  • Apartments: A practical choice for solo travelers or couples looking for easy access to local attractions.**

Top attractions in Enterprise

Enterprise, Oregon, is a fantastic destination for outdoor enthusiasts and those seeking picturesque scenery or a romantic getaway. The area boasts popular attractions like libraries, parks, and lookouts, offering a variety of experiences for families, culture seekers, and nature lovers alike. Whether you’re exploring the beauty of the surroundings or enjoying local culture, Enterprise has something special for every traveler.

  • Red Hill Lookout: Experience breathtaking panoramic views from this scenic lookout, perfect for outdoor adventures and romantic sunsets. It's an ideal spot for hiking enthusiasts seeking a thrilling escape in nature.
  • Chief Joseph Canyon Creek Trail: This eco-friendly park offers a family-friendly atmosphere with trails that wind through stunning landscapes. It's perfect for hiking, picnicking, and enjoying the area's rich natural beauty.
  • Enterprise Public Library: A cultural hub for the community, this library provides a welcoming space for families. Explore a diverse collection of books and participate in engaging programs for all ages.

Things to do recommended for couples

Enterprise, Oregon offers charming experiences for couples. Explore the scenic Wallowa Lake and take a romantic hike in the Eagle Cap Wilderness. Enjoy a cozy evening at local wineries, savoring exquisite wines while surrounded by breathtaking views. Don’t miss the stunning sunsets that create a perfect backdrop for your getaway.

Things to do recommended for families

Families can explore the beautiful Wallowa Lake, perfect for boating and picnicking, or take a scenic ride on the Wallowa Lake Tramway for stunning views. The nearby Eagle Cap Wilderness offers hiking trails suitable for all ages, making it an ideal destination for outdoor adventures.

Things to do recommended for groups

Groups visiting Enterprise can hike the breathtaking trails of the Wallowa Mountains and enjoy a guided tour of the historic town. Don’t miss the scenic tram ride for stunning views and the chance to explore local artisan shops for unique souvenirs.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Enterprise

If you're traveling with a group, family, bringing pets, or planning an extended stay, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Enterprise with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Enterprise with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, as well as look for age-appropriate amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Enterprise: For many families, a vacation wouldn't feel complete without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Enterprise: If you're in search of vacation rentals that offer special deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like parking, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay in and around Enterprise

Enterprise, Oregon, is a charming small town perfect for outdoor enthusiasts and romantic getaways. Explore the picturesque downtown, filled with friendly locals and unique shops. Venture into nearby state parks for breathtaking scenery and recreational activities. Experience the warm atmosphere and family-friendly vibe that makes Enterprise a delightful destination. Whether you're hiking or simply enjoying the views, your vacation in Enterprise promises unforgettable memories.

  • Joseph: Nestled just 6 miles from Enterprise, Joseph is a charming city renowned for its breathtaking outdoor scenery and romantic ambiance. Visitors flock here to explore the stunning recreational areas and enjoy activities such as skiing on the nearby slopes. Joseph is also a gateway to natural wonders, including a picturesque lake and the expansive national state park, where you can hike and take in panoramic views from various lookouts. Whether you're seeking adventure or a peaceful retreat, Joseph offers an unforgettable experience in the beautiful Wallowa Mountains.
  • Troy: Located within the vicinity of Enterprise, Troy is a quaint village that provides a serene escape into nature. This area is perfect for those who appreciate stunning landscapes and outdoor activities. Visitors can explore the recreational areas, enjoy leisurely strolls along the lake, or engage in fishing and kayaking on the nearby river. The village's charm is enhanced by its proximity to the national state park, making it an excellent base for hiking and wildlife viewing. Troy's inviting atmosphere is ideal for couples and nature lovers alike.
  • Lostine: Situated 8 miles from Enterprise, Lostine is a delightful city that invites visitors to immerse themselves in its outdoor splendor. Known for its scenic beauty, Lostine offers a range of activities, including skiing and access to recreational areas that cater to adventure seekers. The area is home to a stunning lake and a national state park, perfect for hiking and picnicking. Don't miss the chance to relax at the local hot springs, adding a touch of relaxation to your outdoor explorations. Lostine captures the essence of a romantic getaway surrounded by nature.

Best time to go to Enterprise

If you're planning a trip to Enterprise, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.2°F (-3.8°C)Light RainMostly CloudyAverageSlightly Low
February26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly Low
March32.9°F (0.5°C)Light RainMostly CloudyAverageAverage
April38.8°F (3.8°C)Light RainMostly SunnyAverageAverage
May48.0°F (8.9°C)Light RainMostly SunnyAverageAverage
June56.5°F (13.6°C)Light RainMostly SunnyModerately HighSlightly High
July67.3°F (19.6°C)No Rain (Dry)SunnyModerately HighSlightly High
August66.7°F (19.3°C)No Rain (Dry)SunnyModerately HighSlightly High
September57.9°F (14.4°C)No Rain (Dry)SunnyAverageAverage
October44.4°F (6.9°C)Light RainMostly SunnyModerately LowAverage
November31.8°F (-0.1°C)Light RainMostly SunnyModerately LowSlightly Low
December23.9°F (-4.5°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Are you interested in saving money on your next adventure? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, booking an extended stay can lead to considerable savings. To discover a Vrbo property that suits your budget, utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy way to plan your trips, allowing you to create new itineraries, pick up where you last left off, or manage your existing plans. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Why people love visiting beautiful Enterprise

The lake and mountains create a pretty picture of Enterprise. This scenic and relaxing city is known for its hiking, shopping and golfing. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Enterprise

Do you want to find attractions to see in the city? Venture out of your vacation home and experience everything that makes Enterprise a fun spot to vacation. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Alpine Meadows Golf Course (0.9 mi / 1.5 km)
  • Ferguson Ridge Ski Area (13.1 mi / 21 km)

Exploring the natural landscape of Enterprise

Travelers enjoy Enterprise for its lakeside setting and mountain views. Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Enterprise. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Wallowa Lake (8.6 mi / 13.8 km)
  • Wallowa Lake State Park (10.4 mi / 16.7 km)
  • Eagle Cap Wilderness Pack Station (11 mi / 17.8 km)
  • Wallowa-Whitman National Forest (16.8 mi / 27 km)
  • Wallowa River (1.1 mi / 1.8 km)
  • Wallowa Lake County Park Public Beach (6.9 mi / 11.2 km)

Frequently asked questions

What is the best area to stay in Enterprise, Oregon, United States of America when booking a vacation rental?
When considering a vacation rental in Enterprise, Oregon, the area surrounding the downtown district is an excellent choice. This charming neighborhood offers a blend of local culture and easy access to stunning natural beauty. You'll find several properties that cater to various preferences, making it a popular spot for visitors.One of the top attractions nearby is the Wallowa Lake State Park, which is superb for outdoor enthusiasts looking to hike, fish, or simply enjoy the breathtaking views of the surrounding mountains. The park's picturesque lake is an ideal setting for picnics and recreational activities, ensuring a delightful experience for families and nature lovers alike.Additionally, the nearby Eagle Cap Wilderness Area provides ample opportunities for hiking and exploring, with trails that showcase the region's stunning landscapes.
How much does it cost to rent a vacation home in Enterprise?
Prices for vacation rentals in Enterprise vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Enterprise to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Enterprise vacation house rentals?
You can find great discounts on house rentals in Enterprise on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Enterprise ski resort rentals?
For the best ski resort rentals near Enterprise, travelers should consider accommodations in the nearby Wallowa Valley, particularly around the town of Joseph, which is approximately a 30-minute drive from the ski areas at Anthony Lakes. This picturesque town offers a range of vacation rentals, including cozy cabins and mountain lodges that feature amenities such as wood-burning stoves, fully equipped kitchens, and sometimes even hot tubs or saunas for post-ski relaxation.In Joseph, visitors can find properties with stunning views of the surrounding Wallowa Mountains, many of which come with outdoor spaces great for soaking in the scenic beauty. The area is also known for its vibrant arts scene, and travelers may appreciate staying close to local galleries and artisan shops.For those seeking a more rustic experience, the nearby town of Enterprise itself offers charming lodges and cabins that emphasize a connection to nature, often featuring large decks, fire pits, and easy access to hiking trails. Guests can enjoy a blend of winter sports and outdoor activities, with many rentals designed to accommodate families or groups looking to unwind after a day on the slopes.
What is the most popular type of vacation rental accomodation in Enterprise?
In Enterprise, condos are the most popular type of vacation rental, with around 13 available within the area. These condos typically feature modern amenities such as fully equipped kitchens, cozy living spaces, and often balconies for enjoying views of the surrounding landscape. They are conveniently located near local attractions like the Wallowa Mountains and nearby hiking trails, making them a great choice for outdoor enthusiasts.In addition to condos, there are several vacation houses, cabins, and cottages available, offering a variety of options for travelers seeking more space or a rustic experience. These properties often include multiple bedrooms, outdoor seating areas, and unique features like fireplaces, suiting families or groups looking for a home-away-from-home atmosphere.
Are there any family house rentals in Enterprise?
In Enterprise, Oregon, families will find a selection of approximately ten vacation rentals suited for their needs. This charming town, located in the Wallowa Valley, offers a backdrop of stunning natural scenery, making it an excellent choice for family getaways. Many of these homes feature spacious layouts, complete kitchens ideal for preparing family meals, and outdoor areas where children can play and explore.The location provides easy access to nearby attractions such as the Wallowa Lake State Park, great for picnics, hiking, and water activities, ensuring that visitors have plenty of options for outdoor adventures. Additionally, the town is close to the historic downtown area, where local shops and eateries can be enjoyed.
Can I find long-stay vacation rentals in Enterprise?
A long-stay vacation rental in Enterprise is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Enterprise?
In Enterprise, Oregon, there are several vacation rentals suitable for remote work, with around 20 options available. These properties typically feature essential amenities like high-speed internet and Wi-Fi, allowing for a productive work environment. Many rentals also include dedicated workspaces with desk and chair setups, ensuring comfort while you focus on tasks.The area is known for its stunning natural beauty, located in the Wallowa Valley near the Wallowa Mountains, making it a great backdrop for both work and relaxation. After a day of remote work, you can enjoy the nearby outdoor activities, including hiking and fishing, or explore the local charm of Enterprise with its shops and restaurants. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Enterprise vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Enterprise with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Enterprise?
In Enterprise, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their meals at their convenience. Many rentals also feature coffee and tea makers for a cozy start to the day. Onsite parking is commonly available, making it easy for travelers to explore the beautiful surroundings without concern for where to leave their vehicles. Additionally, many properties provide workspaces complete with desks and desk chairs, accommodating those who may need to catch up on work or stay connected during their stay.
When is the best time to visit Enterprise for a vacation rental?
The best time to visit Enterprise for a vacation rental is during the peak summer months of June through August, with July being particularly popular among travelers. This season attracts outdoor enthusiasts eager to explore the stunning Wallowa Mountains and partake in activities such as hiking, fishing, and horseback riding. The warm weather, typically ranging from the mid-60s to mid-80s Fahrenheit, creates ideal conditions for enjoying the natural beauty of the area.In addition to the breathtaking landscapes, summer in Enterprise is bustling with local events and festivals that celebrate the region's rich culture and heritage. This lively option invites visitors to immerse themselves in the community, making it a fantastic time for those seeking a vibrant vacation experience.If you're looking for a more budget-friendly option, consider visiting in December. While the temperatures can dip to the low 30s and high 40s Fahrenheit, this month offers a unique charm as the landscape transforms with winter's touch. You can enjoy cozy accommodations and explore the serene beauty of the area, superb for a peaceful getaway.
How early should I book a Enterprise vacation rental?
Book your Enterprise vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Enterprise, Oregon, United States of America?
In Enterprise, Oregon, visitors can immerse themselves in the natural beauty of the Wallowa Valley. The town is a gateway to the stunning Wallowa Lake, which offers opportunities for boating, fishing, and hiking along its picturesque shores. Nearby, the Wallowa-Whitman National Forest provides extensive trails for hiking and biking, attracting outdoor enthusiasts to explore its scenic landscapes.The historic downtown area features charming shops, local art galleries, and cozy cafes, making it a great spot to relax and enjoy the local culture. The nearby Oregon Trail Interpretive Center, located just a short drive away in Baker City, offers insights into the region's pioneer history and is a worthwhile visit for those interested in the area's heritage.Additionally, the annual Wallowa Valley Festival of Arts showcases local talent and adds to the vibrant cultural scene in Enterprise.
Can I change or cancel my Enterprise home rental booking on Vrbo?
To find Enterprise vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Enterprise vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively. Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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