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There are so many amazing getaways in Oregon that you could go to a completely different part of the state every month of the year and not have anything close to the same experience twice. In fact, you should do exactly that this coming year – there’s no time like the present for you to take some road trips and get to know the great state of Oregon a whole lot better. Here, we’ve listed 12 magnificent vacation rentals in Oregon for inspiration – so start booking places to stay and start planning some trips! When the time comes to hit the road each month this year, you’ll be glad that you planned ahead. Save travels and cheers, adventurers!

1. January: Sycamore Lodge near Mount Hood

Mount Hood, Mt Hood, Oregon 97041, USA
Management/VRBO
A fantastic way to start off the new year is with a ski vacation to Mount Hood! This 2,654-square-foot cabin sleeps 8 in three bedrooms, has two full baths, and has a huge stone fireplace where you can cozy up with your traveling companions after a long day on the slopes. You'll also love the hot tub, the fire pit, and the serenity of spending a few days in the forest. You can even bring your dog along! This is a perfect getaway destination to start the year off right. Need even more reason to visit the area? Check out this stunning footage of Mt. Hood:

2. February: Apartment in Historic Victorian Home in Astoria

Astoria, OR 97103, USA
Management/VRBO
Astoria is lovely at any time of year; everyone loves this small town on the river and near the coast. This historic Victorian home has been divided into two apartments and you can rent the second floor apartment for a wonderful weekend getaway. This apartment has two bedrooms, sleeps six, and has two and a half bathrooms. Dogs are welcome, and there's a private viewing porch for you to relax on anytime you like while you enjoy views of the Columbia River. Downtown Astoria is nearby and you can drive to many natural and historical sites with ease. You'll love Astoria in February.

3. March: Hillside Cabin near Mt. Bachelor

Mount Bachelor, Oregon 97703, USA
Management/VRBO
March is an excellent time to get in some more skiing before the season comes to a close, and Mount Bachelor is the perfect destination for doing just that. This luxury cabin is a great choice for your accommodations for this adventure; it sleeps 5 guests in two bedrooms and has three bathrooms. There's a private lake on the property with a trail that goes all the way around it, so be sure to bring your snowshoes! You'll be 12 miles from Bend if you need to run into town and just 6 miles from Mount Bachelor Ski Resort. You'll love curling up by the fireplace or relaxing in the hot tub while the quiet snow falls all around you.

4. April: Historic Cottage in McMinnville

McMinnville, OR 97128, USA
Management/VRBO
A visit to the Willamette Valley to enjoy everything wine country has to offer is an excellent way to welcome springtime! This 100-year-old, 900-square-foot cabin is perfect for 2-4 guests and is within walking distance of historic downtown McMinnville. There's a fenced-in yard and small pets are welcome. Spend a weekend visiting wineries and strolling through the city. What a pleasant way to spend a weekend!

5. May: Victorian Home in Northwest Portland

Portland, OR, USA
Management/VRB
Visiting The Rose City in the spring should be on everyone's bucket list! This Victorian home is close to everything you'll want to see and do, including seeing the roses bloom in the Portland International Rose Test Garden just a little over a mile away. It is 1,970 square feet in size and has room for 8 guests in three bedrooms (plus an additional sleeping space). There are also two full baths, an oversized kitchen, a living room, a formal dining room, and a large deck. This home is simply lovely for a weekend - or longer - in Portland.

6. June: Riverfront House in Florence

Florence, OR 97439, USA
Management/VRBO
In June, the days get warmer and longer so there's no better time to head to the beach! This vacation home is situated right on the banks of the Siuslaw River and is close to both Old Town and the beach. There's lots of light and a big, sunny deck, plus two bedrooms and a loft for up to 6 guests. This home is wonderful for families, friends, or a couple, and you'll have everything you need to make your beach vacation one to remember in Florence.

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7. July: Red Blanket Cabin near Crater Lake National Park

Prospect, OR 97536, USA
Management/VRBO
Crater Lake National Park is calling! It's an exciting place to visit in July. There's so much to see and do in this part of the state at the peak of the summer, and this cabin, near the town of Prospect, can be your home base. This is a custom-built, two bedroom, one bathroom home that sleeps four. The home is surrounded by a young stand of Ponderosa pines and is quiet and relaxing in every way. Spend time on the comfortable front porch and breathe in the mountain air. Here, you can truly get away from it all. Watch this incredible drone footage and you'll catch a glimpse of what makes Crater Lake National Park such a natural wonder:

8. August: Cozy Cottage in Cannon Beach

Cannon Beach, OR, USA
Management/VRBO
Head back to the beach to enjoy the fleeting days of summer in this cozy cottage just steps from gorgeous Cannon Beach and Haystack Rock. It's just 289 square feet in size but it sleeps three guests in two beds and has one bathroom, and it's dog friendly, too! You'll be close to town and many shops and restaurants and there's parking for one vehicle. You and your companions and your dog will love this spot for the perfect beach vacation. Watch this breathtaking footage of Cannon Beach -- we bet you'll be packing your bags in no time!

9. September: 1925 Belle Millhouse Bungalow in Old Town Bend

Bend, OR, USA
Management/VRBO
September is a great time of year to head out to central Oregon to visit Bend. This home is within easy walking distance of the heart of downtown Bend and countless shops and restaurants. It was built in 1925 and is listed on the National Register of Historic Places. It's just 688 square feet in size, but it comfortably sleeps four guests in two bedrooms. This home is well-rated and very charming and it's an excellent choice for accommodations in Bend.

10. October: Country Escape Guest Cabin at Crooked Finger Farms near Silver Falls State Park

Silver Falls, Oregon 97420, USA
Management/VRBO
This guest cottage is on a 67-acre farm that has horses, chickens, a cat, and a friendly dog. It's about 20 miles east of Salem and is a perfect place to enjoy Oregon fall foliage. It sleeps six in five beds in three bedrooms, and also has two full bathrooms. There's plenty of room to make a meal in the kitchen or to relax in the living room. You'll be just seven miles from spectacular Silver Falls State Park and even closer to countless hiking opportunities. This place is special and you'll want to come back every year.

11. November: 1878 Wisdom House in Baker City Historic District

Baker City, OR 97814, USA
Management/VRBO
Head on out to eastern Oregon for a November getaway and stay in this large historic home that was built in 1878. It's quite large and sleeps up to 17 guests in 10 beds in four bedrooms, and there's lots of room for relaxing and hanging out. Walk to shops and restaurants and enjoy everything that Baker City has to offer. After a long day of exploring, soak in the clawfoot tub or cook a meal on the charcoal BBQ that's shaped like a pig. You'll love everything about this special vacation home.

12. December: Cozy Home in Hood River

Hood River, OR 97031, USA
Management/VRBO
Hood River comes alive around Christmastime and there's lots to do in this little town on the river. This two bedroom, one bathroom home is a great place to stay while you're in town, and it's close to all the action, yet is also quiet and relaxing. You'll love the views of the river and the Hood River Bridge from the Deck. It's small but there's plenty of room for up to four guests to have a pleasant winter getaway.

We hope these vacation rentals have helped to inspire you to explore Oregon throughout the coming year! These are just a few of the many amazing options available to you all over the state. Start dreaming, start planning, and start booking your lineup of incredible getaways in Oregon today. As each monthly trip approaches, you’ll be glad that you planned ahead!

If you want to see more fantastic vacation rentals in Oregon, check out our Oregon vacation rentals page for more inspiration!

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

More to Explore

Getaways In Oregon

Beth C. | January 17, 2024

What are some of the best hotels and resorts in Oregon?

There's so much to see and do in Oregon, and fortunately, there are plenty of places to stay while you're exploring. Below you'll find a list of some of the best hotels and resorts in Oregon:

  • Cannery Pier Hotel & Spa, Astoria
  • Tiny Digs Hotel of Tiny Houses, Portland
  • Arch Cape Inn, Arch Cape
  • Brasada Ranch, Powell Butte
  • McMenamins Edgefield, Troutdale
  • Stephanie Inn, Cannon Beach
  • Headlands Coastal Lodge & Spa, Pacific City
  • Atticus Hotel, McMinnville
  • Sentinel, Portland
  • The Allison Inn & Spa, Newberg
  • Hallmark Resort & Spa, Cannon Beach
  • The Coho Oceanfront Lodge, Lincoln City

 

Curious to learn a little bit more about the destinations featured above? Check out our full guide to some of the best hotels and resorts in Oregon. From luxury stays to unique hole-in-the-wall places, you'll find that this list has something for every kind of traveler!

What are the best romantic hotels for couples in Oregon?

If you're planning an Oregon getaway with that special someone, you might consider booking a night or two at any of the following hotels for couples:

  • Fivepine Lodge in Sisters
  • Gilbert Inn in Seaside
  • Newport Belle in Newport

 

From a hotel with a Victorian ambiance to a floating riverboat bed and breakfast, the above hotels for couples are truly unique!

What are some family-friendly places to stay in Oregon?

For those traveling with the whole crew, the following list of family-friendly accommodations in Oregon is sure to impress all ages:

  • Hotel Grand Stark in Portland
  • Out 'n' About Treehouse Treesort
  • Kah-Nee-Ta Resort & Spa

 

 

 

 

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