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Ashland Vacations

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Hotel stay must be within date range of Leave and Return.

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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
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Ashland Vacation Packages

Hotel only $100


3 stars
4.3 / 5 6 reviews

132 N Main Street Map

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... More

Hotel only $79

2 Ashland Hills Hotel and Suites

2 stars
4.3 / 5 76 reviews

2525 Ashland Street Map

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... More

Hotel only $101

3 Stratford Inn

3 stars
4.2 / 5 5 reviews

555 Siskiyou Boulevard Map

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.... More

Hotel only $67

4 Flagship Inn Ashland

2 stars
4.0 / 5 7 reviews

1193 Siskiyou Blvd Map

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... More

Hotel only $90

5 BEST WESTERN Windsor Inn

3 stars
3.4 / 5 22 reviews

2520 Ashland Street Map

Stay at this Ashland, Oregon hotel offering convenient access to the Shakespeare Festival, Southern Oregon University and the Mount Ashland Ski Resort. Conveniently located right off the Interstate 5 in Southern Oregon, the BEST WESTERN Windsor Inn offers comfortable... More

Hotel only $64

6 Super 8 Ashland

2 stars
3.2 / 5 48 reviews

2350 Ashland St Map

Stay 2, Save 15%

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... More

Hotel only $90

7 Holiday Inn Express & Suites ASHLAND

3 stars
4.0 / 5 25 reviews

565 Clover Lane Map

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 Express® Hotel Ashland offers guests the... More

Hotel only $79

8 Cedarwood Inn Ashland

2 stars
2.9 / 5 12 reviews

1801 Siskiyou Boulevard Map

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,... More

9 Manor Motel and Helman House

2 stars
3.3 / 5 4 reviews

476 N. Main Street Map

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... More

Hotel only $75

10 La Quinta Inn & Suites Ashland

3 stars
3.7 / 5 38 reviews

434 S. Valley View Rd. Map

Samsung Flat-panel TVs with 30 channels of HD programming. Easy-access Plug-and-Play feature makes it simple to connect electronics. Nestled in the Rogue Valley, nineteen miles north of the California border, the La Quinta Inn & Suites Ashland is your gateway to the... More