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Experience Jacksonville: A Historic Gem in Oregon Wine Country

Welcome to Jacksonville, Oregon, a picturesque town where history, culture, and wine-country charm come together. Known for its beautifully preserved Gold Rush-era buildings, boutique shops, and scenic vineyards, Jacksonville offers couples the perfect blend of romance and relaxation. With our curated list of top-rated hotels, couples can find the ideal stay, whether it’s a historic inn, a cozy bed and breakfast, or a luxury retreat nestled among the vineyards. Explore the quaint downtown, enjoy wine tasting at award-winning local wineries, or attend a performance at the renowned Britt Music & Arts Festival. Jacksonville invites couples to experience a timeless getaway filled with charm, history, and scenic beauty.

As the holiday season approaches, suites are filling up quickly!Check Availability Now to avoid disappointment!

Historic Downtown Hideaways

Stay in the heart of Jacksonville with easy access to charming shops, wine tasting rooms, and acclaimed restaurants—perfect for couples who love culture and strolls.

  • Jacksonville, Oregon
    105 W Main St, Jacksonville, OR 97530, USA

    The Orth House Inn by Remotion

    5/5(1)
    from $160/night
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    The Orth House Inn by Remotion in Jacksonville, Oregon, offers a romantic retreat infused with historic charm and cozy accommodations. It is situated just steps away from local dining and attractions, making it perfect for couples seeking tranquility.

    • Charming suites
    • King-sized beds
    • A beautiful garden
    • Pet-friendly options
    • Proximity to local attractions

Boutique Luxury Retreats

Indulge in romantic boutique hotels featuring plush amenities, fireplaces, and garden views for a memorable stay that pampers the senses.

  • Jacksonville, Oregon
    240 E California St, Jacksonville, OR 97530, USA

    McCully House Inn

    4.9/5(131)
    from $263/night
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    Escape to the historic McCully House Inn in Jacksonville, OR, where romance meets boutique luxury. Stay in beautifully restored rooms featuring king beds, fireplaces, and garden views. Enjoy intimate amenities that make every couple’s stay memorable:

    • Fireplaces and whirlpool tubs in suites
    • Secluded private patios for two
    • Complimentary bicycles for scenic rides
    • Gourmet on-site pub and bakery
    • English-inspired gardens and event venues

Intimate Cottage Getaways

Escape to a cozy inn or cottage, offering privacy and classic charm for couples seeking peaceful time together in a picturesque setting.

  • Jacksonville, Oregon
    245 N 5th St, Jacksonville, OR 97530, USA

    Magnolia Hotel

    4.9/5(124)
    from $154/night
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    Located in historic Jacksonville, Oregon, the Magnolia Hotel provides a delightful romantic getaway for couples. This boutique retreat offers a cozy atmosphere and dedication to a relaxing experience.

    • Lovingly curated rooms
    • Complimentary breakfasts
    • Proximity to local adventures
    • Eco-friendly practices
    • Serene surroundings

Riverfront Romance Experiences

Delight in scenic stays with river views, private balconies, and tranquil surroundings—perfect for nature-loving duos craving serene moments.

  • Jacksonville, Oregon
    15100 OR-238, Applegate, OR 97530, USA

    The Lindsay Lodge & Restaurant

    4.7/5(85)
    from $195/night
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    Nestled in the picturesque Applegate Valley of Southern Oregon, The Lindsay Lodge & Restaurant offers a romantic getaway with stunning riverfront views and cozy rustic charm.

    • Private balconies
    • Riverfront views
    • The Great Room with fireplace
    • Outdoor courtyard
    • Proximity to vineyards

Wine Country Couples’ Retreat

Relish the charm of Oregon’s wine country with lodging just minutes from tasting rooms, lush vineyards, and romantic countryside adventures.

  • Jacksonville, Oregon
    830 N 5th St, Jacksonville, OR 97530, USA

    Wine Country Inn

    4.6/5(174)
    from $114/night
    Check Availability Now

    Wine Country Inn in Jacksonville, Oregon, provides a romantic getaway surrounded by the region's rich history and stunning landscapes. Couples can enjoy an inviting atmosphere and easy access to local attractions, making it an ideal spot for both relaxation and adventure.

    • Comfortable rooms
    • Charming ambiance
    • Close to renowned wineries
    • Access to outdoor adventures
    • Perfect for relaxation and exploration
Things To Do

Romantic Things To See and Do in Jacksonville, Oregon

Rekindle connection and curiosity with every step through the most inspiring places in Jacksonville, OR. Let your romantic getaway unfold in meaningful moments and memorable discoveries.

  • Historic Downtown & Boutique Strolls

    Historic Downtown & Boutique Strolls

    Jacksonville’s historic downtown feels tailor-made for romantic wandering. Explore antique shops, artisan boutiques, and art galleries housed in lovingly preserved brick buildings. Stop for pastries and coffee in the morning or wine and live music in the evening, every corner radiates charm.

  • Applegate Valley Wine Trail

    Applegate Valley Wine Trail

    Just minutes from town, the Applegate Valley Wine Trail features family vineyards with intimate tasting rooms that feel worlds away from city life. Couples can sip local Pinot Noir, Tempranillo, and Viognier while gazing out over the valley’s golden hills — the perfect toast to love and leisure.

  • Britt Gardens & Summer Concerts

    Britt Gardens & Summer Concerts

    Set in a natural amphitheater under the stars, the Britt Festival is one of Oregon’s most beloved outdoor music events. From jazz to symphony, couples can enjoy world-class performances surrounded by towering pines and the scent of summer in the air.

  • Scenic Walks & Nature Trails

    Scenic Walks & Nature Trails

    For a quiet connection, wander the Jacksonville Woodland Trails, a network of peaceful forest paths right outside downtown. In the fall, golden leaves line the way. And in spring, wildflowers bloom beside the trails. It’s an easy, intimate way to enjoy nature together.

  • Hotel

    Cozy Inns & Candlelit Dining

    Jacksonville’s lodgings combine vintage charm with modern comfort. Stay in a historic inn with antique furnishings, or choose a hillside cottage with private decks and vineyard views. Dine at intimate restaurants serving farm-to-table cuisine, paired beautifully with regional wines.

  • Day Trips

    Day Trips & Southern Oregon Exploration

    From Jacksonville, it’s an easy drive to Ashland’s theaters, Medford’s wine scene, and the Rogue River’s natural beauty. Couples can fill their days with adventure and return each evening to the calm embrace of Jacksonville’s quiet streets and warm glow.

Explore Romantic Experiences & Tours Nearby

Find bookable activities, tours, and scenic spots in and around Jacksonville, OR, directly on the map. Click any pin or "See experiences" to plan your next memorable moments together.

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