Ashland Vacations 2025/2026 from CA $740

Ashland flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

My Place Hotel-Medford OR

CA $740

per person

Jan 16 - Jan 22

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Medford (MFR)

Stay at this 3-star business-friendly hotel in Medford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Medford Railroad Park and Rogue Valley Family Fun Center are located nearby.

Top Ashland hotels deals

Flagship Inn of Ashland

1193 Siskiyou Blvd, Ashland, OR

Free cancellation

Reserve now, pay when you stay

CA $76

CA $84 total

Nov 13 - Nov 14

includes taxes & fees

Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Schneider Museum of Art and ScienceWorks Hands-On Museum are located nearby.

Ashland Hills Hotel & Suites

2525 Ashland St, Ashland, OR

Free cancellation

Reserve now, pay when you stay

CA $133

CA $162 total

Nov 16 - Nov 17

includes taxes & fees

Stay at this 3-star ski hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Weisinger Family Winery and ScienceWorks Hands-On Museum are located nearby.

Stratford Inn

555 Siskiyou Blvd, Ashland, OR

Free cancellation

CA $126

CA $141 total

Dec 1 - Dec 2

includes taxes & fees

Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Ashland Library and Oregon Cabaret Theatre are located nearby.

Green Springs Inn

11470 Oregon 66, Ashland, OR

CA $122

CA $160 total

Nov 20 - Nov 21

includes taxes & fees

Stay at this resort in Ashland. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Cascade-Siskiyou National Monument and Hobart Lake are located nearby.

Comfort Inn & Suites Ashland

434 S. Valley View Rd., Ashland, OR

Free cancellation

CA $127

CA $129 total

Dec 11 - Dec 12

includes taxes & fees

Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allen Elizabethan Theatre and Angus Bowmer Theatre are located nearby.

Ashland Springs Hotel

212 E Main St, Ashland, OR

Free cancellation

Reserve now, pay when you stay

CA $149

CA $187 total

Nov 15 - Nov 16

includes taxes & fees

Stay at this 3-star spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oregon Cabaret Theatre and Allen Elizabethan Theatre are located nearby.

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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.

Popular places to visit

Oregon Shakespeare Festival

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.

Mount Ashland Ski Area

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.

Southern Oregon University

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.

Ashland Vacations

It's always handy to learn the basics about your destination before you rush off on your break. Put a mark next to Ashland on a map now and start getting excited for your adventure!

You'll discover this Medford neighborhood 12 miles (19 kilometers) southeast of the center of the city.

Travelers to Medford will be rubbing shoulders with roughly 75,000 locals.

Places to visit in Ashland

Great theater challenges how we think and asks us to aspire to bigger and better things. Attend a performance at Oregon Shakespeare Festival and expand your way of thinking. Want more nearby options? The intimacy and artistry of theater is difficult to deny. Book your ticket for a performance at Thomas Theatre to experience the magic for yourself! And that's not all there is. Great theater can challenge our expectations and asks us to aspire to more. Sit down for a show at Angus Bowmer Theatre and open your mind to another way of thinking.

Where do you fly into for Ashland?

If you're heading to Ashland, the nearest major terminal is Rogue Valley International Airport (MFR). It's about 14 miles (23 kilometers) northwest from the central area. Select an in-flight movie, sit back and relax and you'll be there in no time at all.

Frequently asked questions

How much are vacation packages to Ashland?

Travelocity provides package deals to Ashland, including flights and hotels, from an impressive CA $740. With all the extra money, you could book some cool tours or maybe tack on a couple of extra nights to your exciting adventure.

How long should my Ashland vacation be?

Generally, people stay 2 nights in Ashland. However, that mightn't be sufficient time for you. If you'd like to see some of the area's hidden gems, why not add a few more nights to your itinerary?

Where can I get the best vacation package deals for Ashland?

With around 400 airline partners and 1,000,000 properties around the world, it's hard to go past Travelocity. Scroll through our impressive range and score an incredible Ashland vacation package. Doesn't it feel amazing when traveling is that easy?

Why should I purchase my Ashland vacation package with Travelocity?

Travel should be about making cherished new memories and leaving all your stresses behind — which is why we have a friendly team of customer service experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best deal available on our superb range of getaway packages. So what are you waiting for? There's no time like the present to lock in the vacation you've always dreamed of.

Will I save money on my Ashland car rental if I bundle it with hotels and flights?

You sure can with our Ashland vacation packages. With one of these, there are lots of ways to stretch your travel budget further. Bundle any two or more car, hotel, flight and tour bookings and see the savings pile up. With your own set of wheels, all the popular attractions around Ashland are just a road trip away.

Which airport is best for Ashland?

Rogue Valley Intl. Airport (MFR), 23 kilometers northwest of the city center, is the jumping off point for many Ashland adventures. That said, Klamath Falls Intl. Airport (LMT) (80 kilometers away from central Ashland) could suit you better.

What is there to do in Ashland?

Ashland is teeming with places to explore, including Oregon Shakespeare Festival and Southern Oregon University. These well-known attractions are at the top of most travelers' itineraries.

Where should I stay when visiting Ashland?

Many people choose to stay at the Stratford Inn. It's a great base for your Ashland getaway.