Luxury Countryside Retreats in Oregon with On-site Restaurants

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Curated Highlights

01Fireplace

02Balcony / Patio

03Luxury

Boutique Hotel

★4.7

Winchester Inn

From

$100

Experience a romantic blend of Victorian elegance and modern luxury at The Winchester Inn in downtown Ashland, Oregon. With gourmet breakfasts, plush accommodations, fireplaces, and award-winning dining, this boutique hotel is perfect for couples seeking history, culture, and relaxation in the heart of the Rogue Valley.

Private Hot TubSoaking TubFireplace

Anniversary Choice ❖ Boutique Hotel

McCully House Inn

Guest Rating

4.9★

From$263

Curated Highlights

01Private Hot Tub

02Soaking Tub

03Fireplace

Anniversary Choice ❖ B&B / Inn

Black Walnut Inn & Vineyard

Guest Rating

4.8★

From$425

Curated Highlights

01Soaking Tub

02Fireplace

03Balcony / Patio

Destination Pulse

Explore Cities with Luxury Countryside Retreats in Oregon with On-site Restaurants

Use this Oregon city guide to continue your search for Luxury Countryside Retreats in Oregon with On-site Restaurants. The destinations below show where matching stays are represented, with city links that keep the relevant filters when matching hotels are available.

Top Cities for This Search

Start with these 4 cities represented in the Luxury Countryside Retreats in Oregon with On-site Restaurants results before browsing the full destination list below.

Ashland

Experience romance and culture in this charming theater town nestled in the Rogue Valley.

McMinnville

Indulge in the charm of McMinnville, where cozy stays, award-winning wineries, and a vibrant downtown create the perfect romantic retreat in Oregon’s wine country.

Jacksonville

Step into the historic charm of Jacksonville, where cozy inns, boutique wineries, and scenic countryside create the perfect couple’s retreat.

Dundee

Escape to the heart of Oregon’s wine country with cozy stays in Dundee, where scenic vineyards, boutique wineries, and intimate settings create the perfect couple’s getaway.