Ashland Vacations

Your Ashland vacation

From family vacations to last-minute romantic getaways, make Orbitz your first and only stop for Ashland vacations. You can customize your trip with flights, hotels and activities to match your travel plans and tastes. Sweeten the pot with extra savings when you book your flight and hotel together.

Create your own Ashland travel plans
Build your own Ashland vacation itinerary. Choose a flight that matches your schedule and a hotel with the amenities you need. Book them together for extra discounts you won't find when booking separately.

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Reach out to an Orbitz travel specialist for Ashland vacation assistance. Our specialists are available around the clock at 1-800-504-3248. We can even help with last-minute Ashland vacations.

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Scope out your Ashland vacation options and savings
With the Orbitz Matrix Display, you can view all your flight and hotel options quickly. Plus, you'll see what you can save on your travel packages when you book them together.
 

Vacation Packages

Ashland Vacation Packages

Ashland Hills Hotel

3 stars
4.4 / 5 61 reviews
On the Quiet Side of Ashland! Stay small, live large in our immaculate suites in a charming country setting close to all that Ashland has to offer. Exemplary service, comfy beds and fluffy towels are our hallmark. Magnificent panoramic views and an intimate courtyard patio showing off nature's beauty combine with our warm hospitality for a perfect stay. Please join us for your next trip to Ashland, for a day or a month, we welcome you here. Enjoy a morning snack featuring hot beverage, fruit, juice, pastry and newspaper delivered to your suite each morning. We invite you to experience true hospitality and incredible value at The Ashland Hills.
Flight + Hotel
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Hotel only
Nightly rates from $82

Cedarwood Inn Ashland

2 stars
4.0 / 5 2 reviews
The Cedarwood Inn is located less than two miles from downtown Ashland, Oregon and the Oregon Shakespeare Festival. Southern Oregon University is less than 1 mile from this hotel. Guests will enjoy a free continental breakfast daily, outdoor pool, hot tub and sauna, exercise room, and free onsite parking. Business services include free wireless internet, and meeting rooms to accommodate a group of 30, with catering and audio equipment available. Please know our front desk is open 7am to midnight daily. All rooms feature free wireless internet, air conditioning, alarm clock/radio, cable TV, iron and board, microwave, mini fridge, hair dryer, free local calls, in room coffee maker, and electronic door locks.
Flight + Hotel
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Hotel only
Nightly rates from $67

Stratford Inn

3 stars
4.0 / 5 1 reviews
100% Non Smoking Facility We are located just four blocks from beautiful downtown Ashland Oregon and four and a half blocks from the Shakespearean theaters. We are close to the hustle and bustle of downtown Ashland but just far enough away to relax from the crowds. While staying at the Stratford Inn you can park your car and walk to the all the downtown restaurants, pubs, galleries and shops you desire. While Ashland is home of the Southern Oregon Shakespeare Festival, Ashland also offers fine dining, shopping, wine tasting, rafting, skiing, golf and an eclectic culture with something for everyone. Don't worry if you forget to pack something, grocery store shopping is nearby. The Stratford Inn has evolved into a "home away from home" for many people who have been staying with us for over two decades, as well as our first time visitors who happen upon us. Our location, heart for hospitality and love for our community is what elevates the Stratford Inn as the cleanest, friendliest and most comfortable place to rest while visiting our incredibly special town. We're happy to have your company, thank you for staying with us!
Flight + Hotel
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Hotel only
Nightly rates from $122

Super 8 Ashland

2 stars
3.3 / 5 40 reviews
Super 8 Ashland is convenient to I-5 adjacent Exit 14. The hotel is 100 PERCENT NON-SMOKING HOTEL and NO PETS ALLOWED. We Have Wireless High Speed Internet, An Indoor Heated Pool, SuperStart breakfast, Micro-Fridges, In Room Coffee Makers, Cable TV with 80 Channels plus three HBO movie stations, Coffee 24-Hours A Day In The Lobby. Free Local Telephone Calls, Free Parking, Group Rates, Guest Laundry Facilities, Hairdryers, Handicapped Rooms/Facilities and Interior Corridors. Shakespeare Festival, Restaurants, Shops/Commercial Services, Mt. Ashland Ski Resort, Southern Oregon Wineries, and Emigrant Lake are located nearby. Must Be 21 Years Old To Rent A Room With A Valid Credit Card.
Value Stay 2, Save 20%
Flight + Hotel
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Hotel only
Nightly rates from $59

Holiday Inn Express Hotel & Suites ASHLAND

3 stars
4.1 / 5 21 reviews
Explore Lovely Ashland, Oregon from Hotel's Location Home to the well-known Oregon Shakespeare Festival, the city of Ashland provides visitors with a variety of cultural, culinary and outdoor experiences, and the Holiday Inn ExpressĀ® Hotel Ashland offers guests the perfect starting point to explore this visually stunning and culturally rich area. The hotel's location in Ashland, Oregon means guests are can easily enjoy the many art galleries, boutiques and the many excellent restaurants in downtown Ashland. Make sure you spend a day or two outdoors exploring scenic Lithia Park or go hiking or skiing at Mt. Ashland. The Pacific Crest Trail winds right by Ashland. White-water rafting and mountain biking opportunities abound. Adults enjoy visiting the numerous local vineyards, where delicious local wines are created. And the Oregon Shakespeare Festival provides world-class theater from February to November, including many original and non-Shakespearean productions. Business guests looking for a convenient Ashland hotel appreciate our location near local companies and Southern Oregon University. Medford, OR is just 12 miles away. As the hotel's guest in Ashland, Oregon, you can enjoy free high-speed, wireless Internet access throughout the hotel, as well as the complimentary, hot Express Start Breakfast Bar, served each morning. You can also use the indoor pool, the whirlpool and on-site Fitness Center to unwind. We hope to see you soon!
Flight + Hotel
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Hotel only
Nightly rates from $129

BEST WESTERN Bard's Inn

3 stars
4.2 / 5 5 reviews
The quaint, unique town of Ashland is home to the world-famous Oregon Shakespeare Festival, and is a hub of culture in Southern Oregon. Our Ashland hotel is within walking distance to the best destinations in Ashland, like Lithia Park and the festivities of the Oregon Shakespeare Festival. Close to Mount Ashland Inn, a haven for ski bums, our Ashland hotel is in the center of this small college town while just a short drive away from the beauty of Mt. Ashland. Centrally located and blocks from everything, theres no better value and location than our Ashland hotel. Walk to hiking trails or visit the unique boutiques and fine dining of the town. Mount Ashland Ski Area is a mecca for snow sports lovers, while the local Rogue River Rafting companies are just a short walk away. No matter what outdoor recreation you prefer, youll find it at your doorstep. Southern Oregon University is nestled in Ashland, but were equally a college and culture-infused town. There are miles of hiking trails surrounding our Ashland hotel, and dont forget to explore the other nearby towns. Historic Jacksonville is just a short drive away, and home to the annual Britt Festival where musicians from around the world perform. Experience the gold rush days in this preserved town, thats been largely unchanged for generations. The Shakespeare Festival runs from February through October, but theres an abundance of options beyond theater. Shop dozens of truly unique stores, and make sure you try a favorite ice cream flavor from Zoes CafƩ. The streets come alive during the summer months, with live music available at the local pubs and in the park. If its your first time in town, try out the natural water fountains for a real surprise. Book your well-appointed room at BEST WESTERN Bards Inn, where youll be in the best location for exploring Ashland!
Flight + Hotel
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Hotel only
Nightly rates from $130

Flagship Inn Ashland

2 stars
4.0 / 5 1 reviews
The Flagship Inn of Ashland is a short 5 minute walk to the Southern Oregon University, and less than 2 miles to the Shakespeare Festival. Located on Highway 99 / Siskiyou Blvd, the Flagship Inn is 20 miles from Mount Ashland Ski Area. Shopping and dining options are within walking distance. This pet friendly hotel provides an outdoor pool, free breakfast, free internet access, and a business center. Guest rooms all include free wi-fi, microwave, mini-fridge, hair dryer, free local calls, alarm clock/radio, electronic door locks, iron/board, cable TV, and air conditioning. Please know our front desk is open 7am - 11pm daily.
Flight + Hotel
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Hotel only
Nightly rates from $80

Ashland Springs Hotel

3 stars
4.3 / 5 18 reviews
Ashland Springs Hotel originally opened its doors in 1925, and today this lovely hotel continues to offer first-class hospitality to those who are drawn by business, the arts or the area's natural beauty. Ashland Springs Hotel is the perfect getaway for your personal retreat or as a home base for regional excursions. The beautifully restored landmark hotel is listed on the National Register of Historic Places and is a member of the Historic Hotels of America. It is just steps from the renowned Oregon Shakespeare Festival. Other nearby attractions and activities include: Oregon Cabaret Theater, Lithia Park, Winery and Gallery Tours, Skiing and Snow Boarding, Golf, Fishing, Tax-Free Shopping, Dining, and pampering at the nearby Waterstone Spa. This elegant boutique hotel offers many fine guest amenities, as well as close proximity to the area's indoor and outdoor attractions. On-site, the property provides business and concierge services, free parking and a cozy fireplace in the hotel's lobby. Reduced rates are also offered at the Waterstone Spa. A wealth of outdoor activities, from skiing to white-water rafting are located nearby.
Flight + Hotel
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Hotel only
Nightly rates from $149

BEST WESTERN Windsor Inn

3 stars
3.5 / 5 17 reviews
Ashland is a truly unique town, and it's best to explore it by foot, which is why our Ashland hotel is centrally located to the best attractions. Whether you're in Southern Oregon for the renowned Shakespeare Festival or to go back in time to the gold mining days in historic Jacksonville, it's all about location. Our Ashland hotel is within walking distance to delectable restaurants and shops, and is just a short drive from the Mount Ashland Ski Area. Some of the best fine dining in the region can be found right here, along with sweet shops sure to satisfy. Our Ashland hotel features a free theatre shuttle, so guests won't miss any of Shakespeare's famous plays. With the largest pool in Ashland, relaxation is a priority here. Spend the afternoon in peace and quiet in our manicured gardens, or slip into one of the many spas in town. A day at Lithia Park is sure to rejuvenate you and is a favorite spot for photographers, families and artists. Of course, if adventure calls, there's plenty to be found. Many guests at our Ashland hotel like to explore the great outdoors. Rogue River rafting features some of the best rapids in the region. Take a hike along one of the many local trails and explore the beauty of the region. From hiking to biking and everything in between, there's something for everyone. You can also choose to relax in your luxurious room at our Ashland hotel, and keep up your fitness regimen with our large fitness room. Southern Oregon University lends a charming small town college vibe to Ashland. For music lovers, the annual summer Britt Festival welcomes world-class musicians from around the world. Whether your taste runs classical or modern, Latin or jazz, this music-centered town is sure to delight. Reserve your spacious room at BEST WESTERN Windsor Inn for a memorable, magical vacation!
Flight + Hotel
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Hotel only
Nightly rates from $119

Manor Motel and Helman House

1 star
3.0 / 5 2 reviews
The Manor Motel is a quaint 1940s style motel in a quiet garden setting. Originally the motel was a 1940s auto court with its own distinctive style. We are within a short walk to the Shakespeare Theaters, restaurants, and The Plaza in downtown Ashland. The Manor features 12 one and two bed units, seven of which have fully equipped kitchens, and five that are equipped with a mini fridge, microwave, and coffeemaker. We have shaded picnic areas with tables and chairs for your leisurely enjoyment. All rooms have direct dial telephones, cable television, and air-conditioning. Helman Guest House and Studios consists of three units. The main house is a charming early 1900s two bedroom that can comfortably sleep up to five guests. It is only three short blocks from the Plaza, restaurants, and theaters. The two studio units, located across a small courtyard from the house, can each comfortably sleep up to three people. Sheets, towels, cookware, and tableware are all provided at Helman House. All of our properties have access to free WiFi and are 100 percent smoke-free. Front Desk Hours is 8 am to 10 pm.
Flight + Hotel
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Hotel only
Nightly rates from $87
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Hotel stay must be within date range of Leave and Return.

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