AshlandLuxury Hotels with Entertainment

List Of Best Luxury Hotels with Entertainment Ashland

We have created a list with the best luxury hotels with entertainment in Ashland, USA. Hope you enjoy it. We think it might be the best of its kind around

luxury hotels in Ashland
Winchester Inn
Hotel
35 South 2nd Street, Ashland, OR 97520, USA

Welcome to Winchester Inn, located just a short stroll of 300 meters from the Oregon Shakespeare Festival in beautiful Ashland. We invite you to relax and unwind in our inviting bar and restaurant, where you can enjoy delicious meals and drinks on our outdoor patio. For your convenience, we also offer free parking during your stay. We look forward to making your visit enjoyable and comfortable!

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Luxury Amenities:

  1. Stay productive with top-notch business services available at your fingertips.
  2. Keep active with a range of sports and activities designed for adventure and fitness.
  3. Savor gourmet dishes at an exquisite restaurant without ever leaving the hotel.
  4. Delight in premium entertainment options that ensure fun-filled evenings throughout your stay.
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luxury hotels in Ashland
McCall House Boutique Hotel
Hotel
153 Oak street, Ashland, OR 97520, USA

Welcome to McCall House Boutique Hotel, located just 200 meters from the Oregon Shakespeare Festival in beautiful Ashland. Here, you’ll find a warm and inviting space where you can relax and unwind. We offer comfortable accommodations surrounded by a lovely garden, as well as free private parking for your convenience. Our cozy shared lounge is a perfect spot to connect with others or enjoy some quiet time. With our commitment to providing a welcoming atmosphere, we strive to make your stay enjoyable and memorable.

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Luxury Amenities:

  1. Keep active with a range of sports and activities designed for adventure and fitness.
  2. Savor gourmet dishes at an exquisite restaurant without ever leaving the hotel.
  3. Delight in premium entertainment options that ensure fun-filled evenings throughout your stay.
  4. Relax at a child-friendly hotel offering safe and engaging activities for the whole family.
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luxury hotels in Ashland
Lithia Springs Resort
Resort
2165 West Jackson Road, Ashland, OR 97520, USA

We want to celebrate with you! If you have a birthday or anniversary coming up, please share the details with us. We’d love to help make your special day even more memorable. We're conveniently located just 2.5 miles from downtown Ashland and the Oregon Shakespeare Festival, making it easy to include us in your plans. Let us know how we can assist you!

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Luxury Amenities:

  1. Wake up to breathtaking ocean views, a stunning start to every morning.
  2. Stay right on the oceanfront and let the sound of waves become your personal soundtrack.
  3. Stay productive with top-notch business services available at your fingertips.
  4. Keep active with a range of sports and activities designed for adventure and fitness.
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luxury hotels in Ashland
Plaza Inn & Suites at Ashland Creek
Hotel
98 Central Avenue, Ashland, 97520, USA

Welcome to Plaza Inn & Suites at Ashland Creek! We’re located right in the heart of downtown Ashland, just a short walk (about 600 meters) from the Oregon Shakespeare Festival. We want you to feel at home during your stay, which is why we offer free WiFi throughout the property, along with complimentary private parking for your convenience. Whether you're here for a getaway or to enjoy some fantastic theater, we're here to support your experience!

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Luxury Amenities:

  1. Stay productive with top-notch business services available at your fingertips.
  2. Keep active with a range of sports and activities designed for adventure and fitness.
  3. Rejuvenate at the state-of-the-art wellness facilities designed for your complete relaxation.
  4. Delight in premium entertainment options that ensure fun-filled evenings throughout your stay.
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luxury hotels in Ashland
Magnolia Hotel
Hotel
245 North 5th Street, Jacksonville, OR 97530, USA

Welcome to Magnolia Hotel in Jacksonville! Just 29 km away from the Oregon Shakespeare Festival, our hotel provides a friendly and comfortable place for you to stay. You can relax in our shared lounge, enjoy complimentary private parking, and take in the fresh air on our lovely terrace. Each of our air-conditioned rooms is designed to provide a cozy atmosphere for all guests. We look forward to making your visit enjoyable and memorable!

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Luxury Amenities:

  1. Keep active with a range of sports and activities designed for adventure and fitness.
  2. Delight in premium entertainment options that ensure fun-filled evenings throughout your stay.
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luxury hotels in Ashland
Resort at Eagle Point Golf Club Lodging
Hotel
100 Eagle Point Drive, Medford, OR 97524, USA

Welcome to the Resort at Eagle Point Golf Club, located in beautiful Medford, just 38 kilometers from the Oregon Shakespeare Festival. Our lodging offers a warm and inviting atmosphere with comfortable accommodations surrounded by a lovely garden. Enjoy free private parking for your convenience. We also have a shared lounge where you can relax and connect with others, as well as a restaurant serving delicious meals. We look forward to making your stay enjoyable and memorable!

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Luxury Amenities:

  1. Stay productive with top-notch business services available at your fingertips.
  2. Keep active with a range of sports and activities designed for adventure and fitness.
  3. Savor gourmet dishes at an exquisite restaurant without ever leaving the hotel.
  4. Delight in premium entertainment options that ensure fun-filled evenings throughout your stay.
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luxury hotels in Ashland
Seven Feathers Casino Resort
Resort
146 Chief Miwaleta Lane, Canyonville, OR 97417, USA

Located just a short drive from Interstate 5 in Canyonville, our resort and casino is designed to offer something for everyone. With over 1,000 video poker and slot machines, there's plenty of excitement for gaming enthusiasts. If you’re looking to enjoy a meal, you'll find a variety of dining options to suit different tastes. For those seeking relaxation, our spa and wellness center features an inviting indoor pool where you can unwind and recharge. We’re dedicated to providing a welcoming atmosphere that caters to all our guests' needs. Whether you’re here to play, dine, or simply relax, we’re excited to have you join us!

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Luxury Amenities:

  1. Take a dip in your own private pool, where tranquility and exclusivity meet.
  2. Stay productive with top-notch business services available at your fingertips.
  3. Keep active with a range of sports and activities designed for adventure and fitness.
  4. Rejuvenate at the state-of-the-art wellness facilities designed for your complete relaxation.
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luxury hotels in Ashland
McCloud Hotel
Hotel
408 Main Street, McCloud, 96057, USA

Welcome to McCloud Hotel, nestled in the beautiful Mount Shasta area! We’re excited to offer a convenient ski pass sales point and secure ski storage for our guests. After a day on the slopes, you can relax at our inviting on-site restaurant, where delicious meals await you. Each room is equipped with a TV for your entertainment. Our friendly staff is available at the front desk around the clock to assist you with anything you might need during your stay. We look forward to making your visit as enjoyable as possible!

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Luxury Amenities:

  1. Enjoy convenient transportation with our exclusive shuttle services for seamless travel.
  2. Stay productive with top-notch business services available at your fingertips.
  3. Keep active with a range of sports and activities designed for adventure and fitness.
  4. Hit the slopes with ease, as premier skiing experiences await right at your doorstep.
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Other cool accommodation lists for Ashland:

Most booked hotels with Entertainment in Ashland

luxury hotels in Ashland
98 Central Avenue, Ashland, 97520, United States of America
7.7
681 reviews
From $229
luxury hotels in Ashland
2165 West Jackson Road, Ashland, OR 97520, United States of America
9.1
668 reviews
From $199
luxury hotels in Ashland
146 Chief Miwaleta Lane, Canyonville, OR 97417, United States of America
8
466 reviews
From $99

Budget hotels with Entertainment in Ashland

luxury hotels in Ashland
146 Chief Miwaleta Lane, Canyonville, OR 97417, United States of America
8
466 reviews
From $99
luxury hotels in Ashland
245 North 5th Street, Jacksonville, OR 97530, United States of America
9.1
14 reviews
From $188
luxury hotels in Ashland
100 Eagle Point Drive, Medford, OR 97524, United States of America
9.5
198 reviews
From $191

Compare the Top Luxury Hotels with Entertainment in Ashland – Addresses, Prices, Stars, Rating, and Review Count

Hotel Name Address Price ($) Star Rating Review Count Book
Winchester Inn 35 South 2nd Street, Ashland, OR 97520, USA 428 5 9.4 351
McCall House Boutique Hotel 153 Oak street, Ashland, OR 97520, USA 332 5 9.8 21
Lithia Springs Resort 2165 West Jackson Road, Ashland, OR 97520, USA 199 4 9.1 668
Plaza Inn & Suites at Ashland Creek 98 Central Avenue, Ashland, 97520, USA 229 4 7.7 681
Magnolia Hotel 245 North 5th Street, Jacksonville, OR 97530, USA 188 5 9.1 14
Resort at Eagle Point Golf Club Lodging 100 Eagle Point Drive, Medford, OR 97524, USA 191 5 9.5 198
Seven Feathers Casino Resort 146 Chief Miwaleta Lane, Canyonville, OR 97417, USA 99 4 8 466
McCloud Hotel 408 Main Street, McCloud, 96057, USA 257 4 8.9 38

Note: The prices for each hotels in Ashland do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here>) to get the latest prices.

Frequently Asked Questions

Popular luxury hotels in Ashland that have a pool include:

Transportation/Shuttle service is available at the following luxury hotels in Ashland:

Some of the best hotels with entertainment in Ashland include those that offer live performances, onsite theaters, and recreational activities. Look for hotels that feature partnerships with local theaters to enhance your stay with cultural experiences.

Yes, many family-friendly hotels in Ashland provide a variety of entertainment options, including game rooms, pools, and organized activities for children. These hotels aim to create a fun and engaging atmosphere for families visiting the area.

Several hotels in Ashland host live music events or theater performances. These venues often collaborate with local artists and theater companies, allowing guests to enjoy vibrant entertainment right at their accommodation.

Hotels with entertainment in Ashland typically offer amenities such as swimming pools, fitness centers, and access to nearby attractions. Additionally, they may have restaurants and lounges that feature regular entertainment schedules.

To find hotels with entertainment near the Oregon Shakespeare Festival in Ashland, consider searching online travel platforms or hotel websites. Many accommodations promote their proximity to the festival and offer package deals or special rates during the event season.

Yes, some boutique hotels in Ashland provide unique entertainment options, such as themed events, art shows, and culinary experiences. These places often pride themselves on offering personalized services and distinctive atmospheres.

Hotels in Ashland often provide various recreational activities such as hiking trips, biking trails, and outdoor games. Some properties also feature spa services, making it easy to combine relaxation with entertainment.

Staying at a hotel with entertainment in Ashland is definitely worth it if you enjoy incorporating cultural experiences into your travel. These hotels often provide easy access to local events and activities, enhancing your overall experience in this charming city.

3-Day Ashland Itinerary If You're Staying at a Luxury Hotel

Day 1:

  • Morning: Start your day with breakfast at the charming Blue Goodies, known for its fresh pastries and local coffee. Afterward, take a leisurely stroll through Lithia Park, where you can enjoy beautiful gardens and scenic walking paths.
  • Afternoon: Explore the world-renowned Oregon Shakespeare Festival. Check out the latest performances or simply tour the stunning theaters. For lunch, stop by the nearby Pasta Pi for delicious Italian fare.
  • Evening: Dine at the upscale Larks Food & Wine, where seasonal ingredients shine in a refined setting. After dinner, catch a show at the Ashland Independent Film Festival, showcasing unique films from independent filmmakers.

Day 2:

  • Morning: Enjoy a gourmet breakfast at Common Grounds Cafe, popular for its locally-sourced ingredients. Following breakfast, visit the Ashland Museum to learn about local history and culture.
  • Afternoon: Afterward, shop at the quaint boutiques in downtown Ashland, such as Shopping in Ashland for unique souvenirs. Enjoy lunch at Pho Ashland, known for its authentic Vietnamese flavors.
  • Evening: For an elegant dining experience, reserve a table at Element, offering innovative dishes and fine wines. Post-dinner, visit the Nature Walks for a relaxing evening stroll under the stars.

Day 3:

  • Morning: Begin your final day at Serenade for Spring for a delightful breakfast amidst lush scenery. Then, head to the Grizzly Peak Winery for a tour and tasting of their exquisite local wines.
  • Afternoon: Venture to the ScienceWorks Hands-On Museum, perfect for interactive exhibits and fun activities. For lunch, try Migrant Son Brewery, which offers flavorful craft beers and tasty bites.
  • Evening: Wrap up your trip with a memorable dinner at Greenleaf Resort, featuring farm-to-table cuisine. For your last night, take a peaceful walk down the Ashland Riverwalk to soak in the tranquil ambiance.

🛏️ Hotels perfect for this itinerary: Lithia Springs Resort, Ashland Hills Hotel & Suites, The Winchester Inn

Where to Stay in Ashland: Best Areas by Traveler Type

Choosing the right area to stay in Ashland is crucial for enhancing your travel experience, as it largely depends on your specific needs and preferences. This charming city boasts diverse neighborhoods, each offering unique amenities and attractions tailored to different types of travelers. Whether you're a couple seeking romance, a family looking for fun, or a solo adventurer craving culture, this guide will help you find the perfect fit for your visit to Ashland.

👫 Where to Stay in Ashland for Couples

Best Areas: Downtown Ashland, North Mountain

Why it’s perfect: Close proximity to intimate dining options and cultural attractions. Scenic parks and romantic walking trails enhance the experience. A vibrant arts scene with live performances adds to the charm.

Top Hotels: The Winchester Inn, Lithia Springs Resort

Top Features: Romantic views overlooking the valley, Cozy outdoor spaces for intimate evenings, Proximity to the Oregon Shakespeare Festival


👨‍👩‍👧 Where to Stay in Ashland with Family

Best Areas: Ashland Creek, South Ashland

Why it’s perfect: Family-friendly parks and recreational areas nearby. Access to educational attractions like the ScienceWorks Museum. A variety of dining options catering to all ages.

Top Hotels: Ashland Hills Hotel & Suites, Quality Inn

Top Features: Spacious family suites, Kid-friendly activities and amenities, Swimming pools for family fun


🧳 Where to Stay in Ashland for Solo Travelers

Best Areas: Downtown Ashland, Historic Railroad District

Why it’s perfect: Vibrant café culture and local shops ideal for exploring alone. Easily accessible public transportation for sightseeing. A range of social activities and events for meeting new people.

Top Hotels: Strange Nature, Ashland Hostel

Top Features: Communal spaces for networking, Close proximity to theaters and galleries, Affordable rates for solo adventurers


👵👴 Where to Stay in Ashland for Seniors

Best Areas: Downtown Ashland, North Mountain

Why it’s perfect: Easy access to cultural sites and leisurely activities. Calm neighborhoods with scenic walking paths. Availability of wellness-focused accommodations and services.

Top Hotels: The Plaza Inn & Suites at Ashland Creek, Comfort Inn South

Top Features: Accessible rooms and facilities, Quiet environments for relaxation, Proximity to health and wellness centers


💸 Where to Stay in Ashland on a Budget

Best Areas: Ashland Historic District, South Ashland

Why it’s perfect: Affordable dining and entertainment options nearby. Access to public transport makes getting around easy. Plenty of free outdoor activities including parks and trails.

Top Hotels: Super 8 by Wyndham Ashland, Motel 6 Ashland

Top Features: Budget-friendly rates without compromising quality, Convenience to main attractions, Simple yet comfortable amenities


💎 Where to Stay in Ashland for Luxury

Best Areas: Downtown Ashland, North Mountain

Why it’s perfect: High-end dining and shopping options within walking distance. Elegant settings and luxurious amenities for a pampered experience. Proximity to the Oregon Shakespeare Festival for cultural enrichment.

Top Hotels: The Ashland Springs Hotel, The Iris Inn

Top Features: Lavish spa services available, Gourmet restaurants on-site, Stunning architectural design and interiors


Where to Stay in Ashland - Quick Guide

Traveler Type Best Areas Top Features
Couples Downtown Ashland, North Mountain Romantic views overlooking the valley, Cozy outdoor spaces for intimate evenings, Proximity to the Oregon Shakespeare Festival
Family Ashland Creek, South Ashland Spacious family suites, Kid-friendly activities and amenities, Swimming pools for family fun
Solo Downtown Ashland, Historic Railroad District Communal spaces for networking, Close proximity to theaters and galleries, Affordable rates for solo adventurers
Seniors Downtown Ashland, North Mountain Accessible rooms and facilities, Quiet environments for relaxation, Proximity to health and wellness centers
Budget Ashland Historic District, South Ashland Budget-friendly rates without compromising quality, Convenience to main attractions, Simple yet comfortable amenities
Luxury Downtown Ashland, North Mountain Lavish spa services available, Gourmet restaurants on-site, Stunning architectural design and interiors