The 8 Best Luxury Hotels with Entertainment in Ashland (2025)

Nestled in the heart of Ashland, the Winchester Inn invites you to indulge in a romantic escape where modern luxury meets timeless charm. With fragrant gardens inviting quiet reflection and elegant interiors that whisper sophistication, this boutique hotel offers a sanctuary for couples and seekers of serenity alike.

Culinary Delights - Savor gourmet breakfasts crafted from local ingredients, where the aroma of freshly baked buns fills the air as you dine al fresco amidst verdant surroundings, setting the perfect tone for your day ahead.

Romantic Hideaway - Each uniquely designed room features plush bedding and cozy seating nooks, promising intimate moments as you unwind with a glass of wine on your private balcony, soaking in stunning mountain views or the vibrant cityscape.

Outstanding Location - Just steps from the renowned Oregon Shakespeare Festival and charming local markets, the Winchester Inn places you at the center of cultural explorations, while the serene sound of rustling leaves creates a tranquil backdrop for your adventures.

Guest Experiences - Imagine waking up to the gentle scent of blooming flowers drifting through your window, complemented by the soft melodies of nature just outside. Guests often mention the delightful surprise of finding handcrafted notes from the attentive staff, making each stay feel uniquely special and personal.

Nestled in the heart of Ashland, where Victorian charm meets modern luxury, McCall House Boutique Hotel invites you to indulge in a sanctuary of elegance and comfort. Just a leisurely stroll from the iconic Oregon Shakespeare Festival, this exquisite hotel offers a tranquil retreat adorned with lush gardens and an inviting sun terrace, perfect for unwinding after a day of cultural exploration or romantic adventure.

Historic Character - Step back in time as you explore the enchanting architecture of McCall House, built in 1883 by the town's former mayor. The intricate details and vintage decor create an ambiance steeped in history that whispers tales of yesteryears, all while ensuring modern comforts at your fingertips.

Culinary Delights - Awaken your palate each morning with an American breakfast exquisitely crafted with seasonal ingredients. Guests rave about the captivating flavors, from perfectly poached eggs paired with vibrant asparagus salad to artisanal biscuits that melt in your mouth—each meal is a delightful start to your day.

Unmatched Location - With an outstanding location just minutes from downtown Ashland and the lush greenery of Lithia Park, McCall House provides the ideal base for both adventurers and culture enthusiasts. The nearby local markets and elegant boutiques make for delightful afternoon strolls, allowing you to immerse yourself in the vibrant community.

Guest Experiences - Upon entering, you're greeted by the intoxicating scent of freshly brewed coffee wafting through the air, hinting at the culinary delight awaiting you. One guest fondly recalled how the staff chatted animatedly about the home's fascinating history, making the stay feel like visiting old friends—a warm invitation to experience Ashland like never before.

Nestled just beyond the charming streets of Ashland, Lithia Springs Resort offers a sanctuary of romance and tranquility. Surrounded by lush gardens and serene koi ponds, this elegant retreat invites you to unwind in luxurious spa-themed suites, each designed to envelop you in warmth and comfort, fostering intimate moments that linger in the heart.

Total Relaxation - Indulge in the natural mineral springs with soaking bathtubs nestled in every suite and bungalow, where the gentle sound of bubbling water floats through the air, providing a perfect backdrop for peaceful afternoons spent in self-care.

Romantic Break - With cozy fireplaces igniting the ambiance in your suite, evenings at Lithia Springs become an intimate escape, inviting couples to cuddle up under soft blankets as they share stories over the flickering flames, creating cherished memories together.

Spa Breaks - The resort's expansive outdoor space, complete with seasonal saltwater pool and soothing hot tub, invites guests to bask in the sun or stargaze while sipping on refreshing beverages, turning each moment into an oasis of calm and rejuvenation.

Guest Experiences - As the scent of freshly baked cookies wafted through the air during afternoon tea, guests found solace in the meticulously kept grounds, often pausing to admire the vibrant flowers or the joyful splash of koi fish, creating a sense of belonging in this slice of paradise.

Nestled in the heart of Ashland, the Plaza Inn & Suites at Ashland Creek is a sanctuary where modern elegance meets timeless romance. The soft murmur of Lithia Creek serenades your mornings while you indulge in gourmet breakfasts that awaken your senses, setting the perfect stage for a getaway steeped in culture and tranquility.

Romantic Retreat - With lush views of the creek from cozy balconies and sumptuous bedding, every room invites couples to unwind and reconnect amidst a backdrop of nature's beauty.

Culinary Delights - Start your day with an expansive hot breakfast, featuring everything from fluffy waffles to locally sourced fruits; it's more than a meal—it's a thoughtful experience that nourishes both body and spirit.

Local Exploration - Just steps away from vibrant shops and dining options, guests can easily immerse themselves in Ashland’s rich cultural tapestry while returning to the comfort of their chic and serene accommodations.

Guest Experiences - A lingering aroma of fresh coffee greets you each morning, and the sound of laughter and clinking dishes fills the air as guests gather over breakfast, sharing tales of nearby art exhibits and spontaneous outdoor adventures.

Nestled in the heart of Jacksonville, Oregon, the Magnolia Hotel invites you to unwind in a sanctuary where modern elegance meets rustic charm. With its immaculately restored spaces and a warm, welcoming atmosphere, this boutique retreat is designed for those seeking intimate relaxation, whether on a romantic getaway or a rejuvenating solo escape.

Romantic Retreat - Immerse yourself in the hotel's serene ambiance, where cozy nooks beckon for quiet conversations, and the soft aroma of fresh flowers fills the air—ideal for couples looking to rekindle their connection.

Total Relaxation - Enjoy the inviting lounge areas that exude comfort, adorned with minimalistic decor that enhances the feeling of home. Here, guests often find themselves lost in a good book or enjoying a cup of organic coffee from the bar—a perfect prelude to a leisurely morning.

Cultural Explorers - Situated just minutes away from Jacksonville's rich heritage, the hotel is an excellent base for cultural adventurers. From local art galleries to historic sites, each step unveils stories waiting to be discovered, enhancing your stay with authentic regional charm.

Guest Experiences - As I strolled through the sun-drenched terrace, the gentle rustle of leaves accompanied the laughter of fellow travelers enjoying breakfast together, while the tantalizing scent of freshly baked pastries wafted through the air. It felt less like a hotel and more like a cherished gathering place, where every corner invited me to linger just a little longer.

Nestled amidst the lush landscapes of Medford, Oregon, the Resort at Eagle Point Golf Club Lodging invites you to embrace a serene escape where luxury meets nature. With its breathtaking mountain views and intimate ambiance, this is the perfect sanctuary for couples and adventurous souls alike, offering an idyllic backdrop for romantic getaways or tranquil retreats. Experience unparalleled comfort in meticulously designed accommodations that feel like your own private oasis.

Romantic Getaway - Indulge in a blissful retreat with elegantly appointed rooms featuring plush furnishings and modern amenities. Some offer private balconies where you can sip morning coffee while basking in the gentle sounds of nature surrounding the golf course.

Total Relaxation - Unwind in the peaceful garden, where fragrant blooms and chirping birds create a serene atmosphere, perfect for yoga sessions or lazy afternoons spent with a good book under the shade of towering trees.

Golf Haven - Step outside and find yourself on the verdant greens of the Eagle Point Golf Club, where you can enjoy a round while marveling at sweeping vistas and perhaps catch sight of local wildlife that adds to the beauty of the landscape.

Guest Experiences - Imagine waking up to the soft rustle of leaves and the distant sound of laughter from golfers enjoying their day. One guest noted the delightful surprise of seeing deer grazing just beyond their balcony, while another praised the immaculate cleanliness of the rooms that felt as fresh as morning dew.

Nestled amidst the verdant hills of Canyonville, Seven Feathers Casino Resort beckons with an enchanting blend of modern luxury and the thrill of gaming. Here, guests find a sanctuary that balances intimate romance with exhilarating entertainment, creating an idyllic escape where every detail invites indulgence and serenity.

Romantic Getaway - Embrace the allure of your surroundings with elegantly appointed rooms featuring plush bedding and tranquil vistas, perfect for couples seeking intimate moments in a luxurious setting.

Spa & Relaxation - Unwind at the soothing spa and health club, where the aroma of therapeutic oils envelops you and the gentle sound of water cascades invites deep relaxation amidst rejuvenating treatments.

Gastronomic Delights - Savor culinary excellence at five distinctive dining venues, from a sophisticated steakhouse to a lively café, where the fragrant sizzle of grilled delicacies mingles with laughter and the clinking of glasses.

Guest Experiences - As you sink into the plush embrace of the bed, the soft whisper of crisp linens surrounds you while you recall winning that fortunate hand at the casino. A quick room service order produces not just delectable bites but also the warm, welcoming smile of staff who seem genuinely invested in your stay.

Nestled in the charming heart of McCloud, California, McCloud Hotel invites you to indulge in an upscale escape where elegance meets nature's grandeur. This romantic hideaway enchants with its lush gardens and cozy nooks, offering a serene backdrop for couples or solo travelers seeking rejuvenation amidst breathtaking mountain vistas.

Romantic Break - Savor intimate moments on the terrace as the sun sets behind the majestic peaks, casting a warm glow that complements your exquisite dining experience, perfectly curated for lovers of fine cuisine.

Total Relaxation - Unwind in thoughtfully designed rooms adorned with plush linens, each equipped with luxurious private baths, allowing you to envelop yourself in tranquility after a day of adventure.

Outstanding Location - Positioned just steps away from hiking trails and ski slopes, immerse yourself in the natural beauty that surrounds you, creating memories as you wander through scenic paths or glide down snow-covered hills.

Guest Experiences - With the aroma of freshly brewed coffee wafting through the air each morning, guests delight in a breakfast spread that feels more like a gourmet feast than a simple meal. Soft laughter from friendly staff echoes in the halls, making everyone feel right at home, while some have even noted the charming quirks of the historic building—a creaky floor here and there adds to the hotel’s character.