Ashland Holidays
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Our guide on where to stay in Ashland
- Historic Railroad District
- Skidmore Academy Historic District
- Historic Downtown District
- Siskiyou-Hargadine Historic District
Historic Railroad District
Step into Ashland's Historic Railway District where Victorian buildings and artistic energy create a cultural haven. Tree-lined streets lead to the famous Oregon Shakespeare Festival theatres and vibrant art galleries housed in restored 19th-century structures. Cobblestone walkways connect charming plazas adorned with bronze sculptures. The district prioritises pedestrians with limited vehicle access, making exploration a pleasure. Farm-to-table restaurants occupy converted Victorians while cosy cafes offer perfect pre-theater dining spots. Historic bed & breakfasts provide intimate accommodation with period furnishings, completing this arts-focused neighborhood's authentic appeal.
Skidmore Academy Historic District
Step back in time to Ashland's Skidmore Academy Historic District, where Victorian-era buildings stand as elegant witnesses to the past. Tree-lined streets lead to ornate homes with wraparound porches and bay windows. The historic academy anchors this charming area, offering a glimpse into 19th-century architectural heritage. This peaceful residential haven sits just steps from the renowned Oregon Shakespeare Festival venues. Theater-goers appreciate the intimate local cafes with seasonal Pacific Northwest cuisine. Visitors can easily explore the district's preserved period homes while enjoying the distinctive atmosphere created by creaking wooden porches and rustling mature trees.
Historic Downtown District
Ashland's Historic City centre District combines 19th-century charm with world-class theatre. The Oregon Shakespeare Festival anchors this walkable area where Tudor-style theatres stand alongside Victorian shopfronts and cobblestone plazas. Art galleries, independent bookshops, and farm-to-table restaurants create a culturally rich atmosphere. Lithia Park borders the district with 93 acres of gardens and walking trails. During festival season, the streets buzz with theatergoers and performers. Most attractions sit within a three-block radius, making exploration easy without a car. Mountain views frame this intimate district where history and performing arts thrive together.
Siskiyou-Hargadine Historic District
The Siskiyou-Hargadine Historic District showcases Ashland's architectural heritage through well-preserved Victorian and Craftsman homes. Tree-canopied streets and manicured gardens create a peaceful residential haven just steps from city centre. Travellers will appreciate the authentic small-town Oregon atmosphere while staying close to cultural attractions. The area sits within walking distance of the renowned Oregon Shakespeare Festival and Lithia Park. Historic bed and breakfasts offer intimate accommodation in restored Victorian homes with period furnishings. Despite its quiet residential character, downtown's diverse dining scene and artisan shops are just a short stroll away.
Discover the most popular places to visit in Ashland
Oregon Shakespeare Festival
What to do in Ashland
Rogue River Family Float & Discovery Park-Rafting and Kayaking
Rogue River Whitewater- Morning Rafting Adventure
Rogue River Whitewater Rafting- Mid Day
Ashland Hotel Deals
Holiday Inn Express & Suites Ashland by IHG
Holiday Inn Express & Suites Ashland by IHG
Frequently Asked Questions
How much does an Ashland holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Ashland costs! Our packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Ashland?
If you're looking to score a cheap Ashland holiday package, consider visiting in December, January and February. You'll generally find better prices on accommodation and flights during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Ashland?
To fully enjoy an Ashland holiday, we suggest booking for 2 days. Divide your time between discovering Thomas Theatre, Schneider Museum of Art and other major sights, on top of exploring neighbourhoods like Siskiyou-Hargadine Historic District and Historic Railroad District. If you've got some spare time, add a tour or day trip to your Ashland holiday itinerary.
Is it worth booking a holiday package to Ashland?
Whether you want to explore top sights like Oregon Shakespeare Festival and Lithia Park on your Ashland holiday, or coming for its great cafes, cycling and hiking, there's something for everyone here. With so much to see and do, you'll quickly learn why so many travellers think Ashland is a good holiday destination.
How to find the best Ashland package deals?
Bagging a cheap Ashland package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalise your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Ashland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book an Ashland holiday as a package?
You can enjoy significant savings on your Ashland break by booking a tailored holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Ashland?
Score amazing discounts by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Ashland trip.
How to plan a trip to Ashland?
- Choose your travel dates: The things you plan to do in Ashland and your favourite season will help you decide when to get away.
- Calculate your budget: Ensure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Ashland.
- Decide your trip length: Consider how much time you'd like to spend exploring Ashland. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Combine your airfare and accommodation: After you've settled on your dates and duration, lock in the right Ashland holiday package for you.