Ashland Vacations

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Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
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Historic Downtown District

3 out of top 10 points of interest in this area
5/5(133 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

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Ashland Hotel Deals

Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is AED 198 per night from Nov 13 to Nov 14
AED 198
AED 221 total
13 Nov - 14 Nov
includes taxes & fees
8.6/10 Excellent! (1,132 reviews)
Pl

Reviewed on 8 November 2025

Flagship Inn of Ashland
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
Fully refundableReserve now, pay when you stay
The price is AED 348 per night from Dec 7 to Dec 8
AED 348
AED 425 total
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (1,498 reviews)
Good, clean, comfortable

Reviewed on 7 November 2025

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundable
The price is AED 331 per night from Dec 7 to Dec 8
AED 331
AED 369 total
7 Dec - 8 Dec
includes taxes & fees
9.2/10 Wonderful! (1,568 reviews)
Very pleasant staff, pretty good sound insulation although I did hear someone snoring, and I liked the breakfast. The pool room was clean and the water was a good temp, although I didn’t use it. There was a monitor in the lobby I noticed that said the pool and hot tub are salt water, which I was ...

Reviewed on 7 November 2025

Stratford Inn
See all 768 properties in Ashland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Ashland

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

4.5/5(265 reviews)

You can make plans for a show at Oregon Shakespeare Festival during your trip to Ashland. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.

Oregon Shakespeare Festival
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

Mount Ashland Ski Area

4/5(70 reviews)

Hit the slopes in Ashland with a visit to Mount Ashland Ski Area. Discover the top-notch restaurants and lively festivals in this walkable area.

Mount Ashland Ski Area

Southern Oregon University

4.5/5(146 reviews)

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's acclaimed theater scene and entertainment choices.

Southern Oregon University

Frequently asked questions

How do I find cheap flights to Ashland that have flexible change policies?
At Expedia, we've been channeling our inner gymnast to provide you with the most flexible fares around town. Simply check the "No change fee" box directly under the "Flexible change policies" filter to find your ideal flight to Ashland.
Which airlines fly to Ashland?
Lock in a seat with one of these airlines and exciting Ashland will be yours to discover:

  • Alaska Airlines - 173 flights to or near Ashland each month, including 173 flights to Rogue Valley Intl. Airport (MFR) per month.
  • Delta Air Lines - 147 flights to or near Ashland each month, including 147 flights to Rogue Valley Intl. Airport (MFR) per month.
  • United Airlines - 121 flights to or near Ashland each month, including 121 flights to Rogue Valley Intl. Airport (MFR) per month.

How can I find cheap tickets to Ashland?
An effective strategy for walking away with cheap fares is to be flexible with your travel dates. Begin with searching for your flight to Ashland, then click on the "flexible dates" box for a list of prices for nearby days. Another handy tip? Book well ahead. For an idea of costs, was the best price for a flight to Ashland in the last seven days.
How much is a flight to Ashland?
If you were jetting one way from (), you could've nabbed a low-cost fare for in the last seven days. Round-trip flights to Ashland ranged from only to over the same period.
What are the most popular airports to fly into in Ashland?
Get ready to pack your bags and jet into Rogue Valley Intl. Airport (MFR), Ashland's primary flight hub. Book a ticket on one of the 529 flights that touch down at this popular destination every month.
When is the cheapest time to fly to Ashland?
Flying on a Tuesday, followed by a Monday, is generally the best way to get the cheapest airfare. Stay away from the weekends if possible, because Saturday is typically the most expensive day. Spend the funds you saved having an awesome time in Ashland instead!
How much is a plane ticket to Ashland?
Plane tickets ranged from just to in the last seven days. When you're ready to book, we're here to help you secure an amazing deal to Ashland.
What months are the cheapest to book a flight to Ashland?
An excellent month to purchase affordable fares to Ashland is February. It's worth remembering that in the U.S, the most expensive time to secure a seat is the festive month of December.
How long is a flight to Ashland?
Whether or not you'll have time for a long snooze or just a quick nap depends on where you're flying from in the U.S. To make planning your trip a little easier, here are the average flight times for three sought-after domestic routes to Ashland:

  • Seattle, WA (SEA-Seattle - Tacoma Intl.) to Rogue Valley Intl. Airport (MFR) - 1 hour and 22 minutes
  • Denver, CO (DEN-Denver Intl.) to Rogue Valley Intl. Airport (MFR) - 2 hours and 44 minutes
  • Salt Lake City, UT (SLC-Salt Lake City Intl.) to Rogue Valley Intl. Airport (MFR) - 1 hour and 57 minutes