Deals on vacations and trips to Ashland

Save when you book Ashland package deals

Choose two or more items and save on your trip:

Ashland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $957, price is now $826 per person
$826
per person
Oct 1 - Oct 4
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Medford (MFR)
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a communal living room are also on offer.
Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was $1,423, price is now $1,244 per person
$1,244
per person
Oct 1 - Oct 4
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Medford (MFR)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A terrace, a garden, and dry cleaning are also on offer.
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $1,715, price is now $1,512 per person
$1,512
per person
Oct 15 - Oct 20
found 4 hours ago
Roundtrip flight included
Duluth (DLH) to Medford (MFR)
This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A business center, a garden, and a lobby fireplace are also on offer.
The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Historic Railroad District
Price was $1,020, price is now $903 per person
$903
per person
Oct 1 - Oct 4
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Medford (MFR)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $983, price is now $876 per person
$876
per person
Oct 1 - Oct 4
found 22 hours ago
Roundtrip flight included
Dallas (DFW) to Medford (MFR)
This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the express check-out.

Top Ashland hotels deals

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd. Ashland OR
Free Cancellation
$115 nightly
The price is $117 total per night
$117 total
Aug 27 - Aug 28
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Hot Tub
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
$143 nightly
The price is $160 total per night
$160 total
Sep 7 - Sep 8
Total with taxes and fees
This smoke-free hotel features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
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
$82 nightly
The price is $91 total per night
$91 total
Aug 17 - Aug 18
Total with taxes and fees
A restaurant and a seasonal outdoor pool are featured at this hotel. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street Ashland OR
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $188 total per night
$188 total
Aug 16 - Aug 17
Total with taxes and fees
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A 24-hour business center, a garden, and luggage storage are also on offer.
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
$111 nightly
The price is $124 total per night
$124 total
Aug 31 - Sep 1
Total with taxes and fees
This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
Free Cancellation
Reserve now, pay when you stay
$172 nightly
The price is $191 total per night
$191 total
Aug 16 - Aug 17
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A 24-hour business center, a terrace, and a library are also on offer.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Ashland
View all properties
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

Take a vacation in Ashland, Oregon, and experience everything from internationally renowned Shakespeare performances to forensic investigation lessons into crimes against globally endangered species. On the same trip, Ashland rental cars can carry you through the beauty of Southern Oregon's Siskiyou National Forest to the shores of the Pacific Ocean. Travelocity's affordable Ashland vacations ensure you can indulge in all your Southern Oregon adventures.

World Class Attractions

Nature is intrinsic to Ashland's character and personality. As you explore 93-acre Lithia Park, you'll find that its two ponds, Japanese garden, band shell, and miles of trails make it a single destination for many of your multiple pursuits. You'll immerse yourself in deep nature as you hike or bike the 25-mile Bear Creek Greenway on your way from Ashland to Central Point. At Ashland's National Fish and Wildlife Forensics Laboratory, the world's only forensic facility investigating crimes against animals, you'll be fascinated by how INTERPOL and other defenders of endangered species have accessed its resources.

World Class Events

Ashland's world famous Oregon Shakespeare Festival (OSF) is only one of the many cultural events you'll discover. From February through October, you can experience up to 11 OSF plays, as well as numerous other arts and cultural events. In summer, you'll revel in small-town Americana during the July 4th Celebration, with its fun run, parade, and fireworks. In early November, your palette will savor Ashland's amazing local foods and its equally amazing local wines at the Ashland Culinary Festival. Over Christmas, downtown Ashland hosts live entertainment, and you'll be dazzled by more than one million Christmas lights.

Ashland's international artistic fame means its amenities are also world-class. Use Travelocity and save up to $537 by booking your flight and hotel together and gain the best rates at any of the many Ashland hotels. Travelocity's Ashland vacation packages offer the flexibility and variety of travel and accommodation options to ensure you enjoy your perfect Oregon vacation.

Frequently asked questions

How much are vacation packages to Ashland?
Travelocity provides package deals to Ashland, including flights and hotels, from an impressive $826. 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), 14 mi northwest of the city center, is the jumping off point for many Ashland adventures. That said, Klamath Falls Intl. Airport (LMT) (50 mi 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.
Casey State Recreation Site near Medford, Oregon
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.

Explore More Ways to Travel with Travelocity