Boutique hotels, cozy Airbnbs, and dreamy vineyard retreats for couples looking to escape. Whether you’re celebrating an anniversary, planning a mini-moon, or just craving some quiet time with your person, Oregon is full of hidden-gem escapes and romantic stays. From wine country to the wild coast, this romantic Oregon getaway weekend guide is here to help you find the perfect place to unwind, reconnect, and soak up the beauty of the Pacific Northwest.

Below you’ll find my favorite handpicked Airbnbs, boutique hotels, and vineyard retreats that are perfect for a cozy couple’s weekend.

🌿 Willamette Valley & Wine Country

The Setting Inn – Newberg, OR

Tucked in the heart of Willamette Valley wine country, The Setting Inn offers a serene, high-end experience perfect for couples. Think vineyard views, dreamy sunrise breakfasts, and cozy firepits at night. Bonus: It’s just minutes from some of Oregon’s best wineries.

Why we love it: Elegant, modern farmhouse vibes with a touch of European charm.
Perfect for: A wine-filled, romantic Oregon getaway weekend.

Youngberg Hill Inn – McMinnville, OR

A working vineyard and inn in one, this spot offers sweeping valley views, charming rooms, and on-site wine tastings. It’s peaceful, elevated, and absolutely made for slow mornings and golden hour strolls through the vines.

🏙️ Romantic Stays in Portland

The Benson Hotel – Portland, OR

Old-world elegance in the heart of the city. If you love vintage interiors, marble staircases, and swoon-worthy lobby photos, The Benson is your perfect match. Walk to local restaurants, book a couples massage, or spend the evening sipping cocktails in their historic bar.

Why we love it: Classy, iconic, and full of character — ideal for couples who want a mix of romance and city adventure.

Curious how The Benson photographs? See Norma & Patrick’s engagement session at this vintage-inspired hotel.

The Bidwell Marriott – Portland, OR

A newly renovated boutique-style hotel with a modern feel and excellent downtown access. Great for couples who want sleek style, good food, and walkability.

Perfect for: A city break with a romantic rooftop cocktail vibe.

🏔️ Mountain & Forest Escapes

Woodlands House – Sandy, OR (Airbnb)

Nestled among the evergreens, this cozy cabin-style Airbnb is the perfect forest retreat. Curl up with a book by the fireplace, sip wine in the hot tub under the stars, or take a scenic hike nearby.

Why we love it: Rustic luxury that still feels intimate and romantic.
Tip: Book in fall or winter for that true cozy getaway feel.

The Society Hotel – Bingen, WA (just across from Hood River)

While technically in Washington, it’s too good not to include. This minimalist hotel + spa offers a Scandinavian-inspired retreat near the Columbia Gorge. Soak in the outdoor hot tubs, sip tea in the library, or book a forest massage.

🌊 Coastal Charm

Hart’s Camp Airstreams – Pacific City, OR

Want something playful and unique? These chic, remodeled Airstreams are steps from the beach. Ride fat bikes through the dunes, roast s’mores, and fall asleep to the sound of the ocean.

Perfect for: A quirky and cozy beach getaway with a retro twist.

Baywood Shores B&B – Lincoln City, OR

A classic bed and breakfast with sweeping bay views and that cozy, nostalgic feel. The rooms are comfy, and the breakfast is homemade — the kind of spot where time slows down.

💡 Tips for Planning Your Romantic Oregon Getaway Weekend

• Book in advance. The best spots fill up fast, especially in summer and fall.
• Go mid-week. You’ll get better rates, quieter stays, and more flexibility.
• Add something personal. Think wine tastings, a flower delivery, or a handwritten note. It’s the little things that make memories.

Ready to Plan Your Dreamy Weekend?

Whether you’re cuddling up in a cabin, sipping wine in the valley, or walking hand-in-hand through downtown Portland, Oregon is full of places to make you fall in love all over again. Save this guide, share it with your person, and start dreaming up your romantic Oregon getaway weekend.

And if you’re looking for a photographer to document your weekend or turn it into a mini session — I’d love to hear from you.