The 7 Most Romantic Getaways in Oregon

The 7 Most Romantic Getaways in Oregon

Describe your perfect date. Long walks on the beach, watching the sun set together, Netflix and chill, or high action and a grand adventure…Whatever gets you in the mood, these are some of the most romantic getaways in Oregon, and they cover the entire range of everything romance can be.

Over the past decade or more, my husband and I have visited many of these places. A few of them are still on my bucket list. But whether you’re celebrating an anniversary, Valentines Day, or just wanting to spend some quality time together, these getaways won’t disappoint.

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FivePine Lodge, romantic getaways in Oregon

1. FivePine Lodge in Sisters

One of the most romantic getaways in Oregon is FivePine Lodge, located on the edge of Sisters in Central Oregon. Tucked in between the pine trees, the resort’s private cabins offer its guests uninterrupted intimacy. My husband and I celebrated our 10 year anniversary here and I’m still dreaming of that weekend!

Imagine a quiet evening, a bottle of local wine, and just the two of you snuggled up by the fireplace. The next morning, you wake up slowly together over a cup of coffee, lounging on your own private patio, staring off into the forest.

Later that day, you meander through the pines to Shibuii Spa for a relaxing couples massage. Then you end your evening with dinner at Three Creeks Brewing Company and a movie at the Sisters Movie House.

This resort may have a rustic appeal, but all the amenities speak to luxury. And with everything you could want or need close at hand, FivePine Lodge has the perfect recipe for a romantic getaway.

TIP: Try out the Ultimate or Classic Romance Package and let FivePine Lodge help set the mood for you. The packages include at minimum a bottle of wine, massages at Shibuii Spa and movie tickets!

⭐️ Click here to check availability at FivePine Lodge ⭐️

Pacific City, romantic getaways in Oregon

2. Headlands Coastal Lodge & Spa in Pacific City

If long walks on the beach and sunsets over the ocean is more your style, then this is the perfect romantic getaway in Oregon for you. Headlands Coastal Lodge is located in Pacific City, just two hours from Portland.

Pacific City is one of my personal favorite spots, and I try to make it there at least once a year. It’s a bit off the beaten path, but that only adds to its appeal.

Headlands Coastal Lodge sits right on the edge of Cape Kiwanda State Natural Area, with a stunning ocean vista of Haystack Rock. And every single one of their rooms boasts an ocean view and a private balcony (or patio), so you really can’t go wrong here.

What really sets up Headlands apart though, is their amenities. They’ve got all the basics of course, including an outdoor hot tub with a view of the rock and a spa, perfect for couples massages.

However, they also offer “Adventure Coaches,” ready to help you plan, or even guide you, on a Pacific Northwest adventure. Always wanted to try yoga on the beach? Want to go kayaking, clamming or crabbing, but don’t know how or don’t have the gear? They’ve got you covered.

Check out a full list of the possibilities on Headlands’ website here. With so many options, this romantic Oregon getaway is definitely the whole-package deal.

TIP: About an hour before sun down, hike up to the top of the dune at Cape Kiwanda to share an unforgettable sunset together. If you go up the side nearest the ocean, it’s not quite as steep as going up the front.

⭐️ Click here to check availability at Headlands Coastal Lodge & Spa ⭐️

3. Timberline Lodge

Timberline Lodge, near the summit of Mt. Hood, is another great romantic getaway for couples. At 6,000 feet elevation, this imposing and rustic 1937 lodge boasts a stunning alpine view.

I visited the lodge one sunny summer day while on a girls’ trip. But I couldn’t help imagining my husband and I returning one winter day and snuggling up together by the hearth.

If you love the snow, plan your stay in the winter months for skiing and snowshoeing. The lodge has such a cozy atmosphere, perfect for you and your partner to warm up together in.

However, Timberline is equally beautiful in the spring and summer months. During the spring, the side of Mt. Hood is covered in wildflowers. And the summer months are best if you plan to climb to the summit.

But where ever your adventures may take you, at the end of the day you’ll love relaxing in your hotel room on a luxurious feather bed.

TIP: Set the mood right by booking your stay in one of the rooms with a king size bed. These rooms offer a fireplace, perfect for warming up in each others’ arms after a day in the cool mountain air. Top it off with the Alpine Massage Package, an in-room 90 minute couples’ massage by the fire! (Package is only available in King and Corner rooms.)

⭐️ Click here to check availability at Timberline Lodge ⭐️

4. Heceta Lighthouse B&B in Florence

We celebrated our 5 year anniversary at the Heceta Lighthouse B&B, and I’ve been dying to go back ever since. Just picture this. You wake up to the sound of the ocean. Still a bit sleep drunk, you pull the sheer curtain aside to reveal waves crashing on the beach, just below your room.

Last night, the two of you strolled along that quiet little beach, holding hands, barefoot in the sand. This morning you have a seven course breakfast, with all locally sourced ingredients. And this afternoon, there’s wine tasting and cheese downstairs in the parlor.

This unforgettable bed and breakfast occupies an old Victorian home that once served as the lighthouse keeper’s house. It sits perched on a cliff top overlooking the Pacific Ocean. And through the windows in the north stairwell, you catch a glimpse of the Heceta Head Lighthouse, standing tall against the coastline.

The house is filled with character and interesting relics from a bygone era. With the house’s deep charm, coupled with just the right bit of seclusion and the dramatic surrounding landscape, this bed and breakfast makes it to the top of the list for one of the most romantic getaways in Oregon.

TIP: I highly suggest booking one of the Mariner’s Rooms (I & II) for a view of the ocean, or the Lightkeeper’s Room for a view of the lighthouse.

⭐️ Click here to check availability at Heceta Lighthouse Bed & Breakfast ⭐️

5. McMenamin’s Crystal Hotel

If the rush of the city is more your speed of romance, then McMenamin’s Crystal Hotel is the perfect Oregon getaway for you. I have to confess, I think I may be in love with McMenamin’s. Although McMenamin’s is a PNW based chain, the one thing they all have in common is that they are all unique.

Many of their hotels occupy historic buildings, preserving their charm and character for everyone to appreciate and admire. Located on the edge of the Pearl district in downtown Portland, McMenamin’s Crystal Hotel occupies a fabulous 1911 flatiron building.

Each of the Crystal Hotel’s rooms reflect a different musician or song previously featured at the nearby Crystal Ballroom. Plan your getaway so you and your partner can catch a concert of your favorite band at the Crystal Ballroom.

Before the concert, you’ll have plenty of time to explore Portland. You can grab lunch at a food truck. Browse through music at Everyday Music, the record shop that’s just a three-minute stroll down the street. Or go relax together in your hotel’s heated soaking pool.

TIP: If you have tickets to a concert at the Crystal Ballroom, be sure to mention so when you book your lodging at the Crystal Hotel for 15% off your stay.

AND ONE MORE TIP: If you love McMenamin’s as much as I do, sign up for their passport program and start exploring more of their locations. And try the Cajun tots! 🤌🏻

⭐️ Click here to check availability at McMenamin’s Crystal Hotel ⭐️

6. Umpqua Hot Springs

Umpqua Hot Springs is one of the more rustic and remote romantic getaways in Oregon. Come here to strip away the noise of the outside world, where you can really focus on one another.

These natural hot springs sit terraced upon a cliff side, with a breathtaking view overlooking the North Umpqua River. A short but steep hike of 0.4 miles will bring you to your destination. Here, you can relax and rejuvenate together under the towering trees of the Umpqua National Forest.

Then complete the experience by glamping in a cozy canvas tent at the nearby campground, Umpqua’s Last Resort. You can warm up together by the campfire or in your king size heated bed!

Although the hot springs are open year round, the best seasons to visit are typically spring and fall. During the winter, roads leading in may be closed due to snow, and you may have to hike or snow shoe about 2.5 miles in to reach the springs. And during the summer, temperatures may be too hot for comfort.

TIP: Crater Lake National Park is only 75 miles away. If you plan your trip right, you may be able to incorporate a visit to this beautiful national park as well.

⭐️ Click here to check availability at Umpqua’s Last Resort ⭐️

7. Willamette Valley Wine Country

When it comes to fine wines, there is some speculation that Oregon’s Yamhill County may be the new up-and-coming Napa Valley. Located in the Willamette Valley, its lush, rolling green hills are covered in boutique wineries. And what could be more romantic than a long weekend exploring these hundred-plus wineries?!

Complete the experience with a stay at the Chehalem Ridge Bed & Breakfast, just on the outskirts of Newberg (a half hour from Portland). This beautiful 5-bedroom house sits atop the mountain with sweeping views of the surrounding wineries below.

You’ll start your day off right with a hearty, homemade breakfast. Chef Kristin serves up freshly baked goods along with homemade jams and jellies. Her meals are always in season, and many of her ingredients are locally sourced.

After breakfast, you’ll be ready to set out to see the countryside and do some wine tasting. A few excellent wineries near your bed and breakfast include Bergstrom Wines, Adelsheim Vineyards, and Chehalem Winery (no relation with the B&B).

There are so many options though, I couldn’t possibly list all the nearby wineries in this post! You can click here for a full list of Chehalem Ridge B&B’s winery recommendations.

TIP: Many wineries in this area now require reservations for wine tasting. However, with over 500 wineries in the Willamette Valley, this may be an overwhelming task! Luckily, Chehalem Ridge Bed & Breakfast offers a planning service and will book reservations for you for a small fee. Click here for more information on their Winery Itinerary Service.

⭐️ Click here to check availability at Chehalem Ridge Bed & Breakfast ⭐️

Final thoughts on these romantic getaways in Oregon

Many of these romantic getaways in Oregon have such a cozy feel to them. And what’s more romantic than getting cozy with the one you love?! With a range from hotels to bed & breakfasts to glamping, there really is something here to fit every couple.

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