Book Exclusive Ashland Vacation Packages

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Ashland flight + hotel packages

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

Lithia Springs Resort

3 out of 5
Price was CA $1,096, price is now CA $944 per person
CA $944
per person
Dec 9 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Medford (MFR)
Stay at this B&B in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). 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 Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was CA $1,247, price is now CA $1,057 per person
CA $1,057
per person
Dec 9 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Medford (MFR)
Book a stay at this business-friendly 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.
Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was CA $1,528, price is now CA $1,315 per person
CA $1,315
per person
Dec 9 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Medford (MFR)
Stay at this inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Oregon Shakespeare Festival and Oregon Cabaret Theatre are located nearby.
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was CA $1,460, price is now CA $1,260 per person
CA $1,260
per person
Dec 9 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Medford (MFR)
Stay at this B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oregon Shakespeare Festival and Allen Elizabethan Theatre are located nearby.
Rosewood Collective- House & Studio

Rosewood Collective- House & Studio

3 out of 5
Price was CA $2,160, price is now CA $1,880 per person
CA $1,880
per person
Dec 9 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Medford (MFR)
Stay at this vacation home in Medford. Enjoy free WiFi, free parking, and a sauna. Popular attractions Blackbird Statue and Medford Carnegie Library are located nearby.

Top Ashland hotels deals

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Free cancellation
Reserve now, pay when you stay
The price is CA $160 per night
CA $160
CA $193 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly 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.
Pool
Hot tub
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd. Ashland OR
Free cancellation
The price is CA $159 per night
CA $159
CA $161 total
Oct 5 - Oct 6
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.
Pool
Hot tub
Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
Free cancellation
Reserve now, pay when you stay
The price is CA $101 per night
CA $101
CA $112 total
Oct 25 - Oct 26
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.
Pool
Breakfast included
Best Western Windsor Inn

Best Western Windsor Inn

2.5 out of 5
2520 Ashland St Ashland OR
Free cancellation
Reserve now, pay when you stay
The price is CA $159 per night
CA $159
CA $177 total
Oct 25 - Oct 26
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 Weisinger Family Winery and ScienceWorks Hands-On Museum are located nearby.
Pool
Hot tub
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is CA $122 per night
CA $122
CA $136 total
Oct 13 - Oct 14
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.
Pool
Hot tub
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
98 Central Ave Ashland OR
Free cancellation
Reserve now, pay when you stay
The price is CA $228 per night
CA $228
CA $254 total
Oct 5 - Oct 6
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.
Breakfast included
Pet-friendly
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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.

Stay near popular Ashland attractions

A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.
Photo by Patrick Glassford
Open Photo by Patrick Glassford

Oregon Shakespeare Festival

9.2/10 (620 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.
See properties

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 $944. 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.

Photos of local treasures

Browse Ashland vacation photos for more inspiration

A deer on a road with vegetation on the sides.
A picnic area with benches and a river.
A town with autumn-colored trees, a mountain range, and a mix of residential and commercial buildings.
A stone bridge over a calm stream with autumn leaves.
A tranquil pond surrounded by vibrant autumn foliage, a stone path, and a wooden bench.

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