Ashland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Ashland Vacation
Create your own exciting adventure with a tailor-made vacation package to Ashland. Its cultural experiences, progressive thinking and spectacular views are just the start of what you can expect in this interesting city. Ready to explore your surroundings? Oregon Shakespeare Festival, Southern Oregon University and Lithia Park are just three of the best places to visit during a trip to Ashland. No matter your travel plans or the size of your budget, putting together a tailored Ashland vacation is simple with Expedia.
Top Ashland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hummingbird Estate Wine & Suites
CA $1,392
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Medford (MFR)
9.6/10 Exceptional! (176 reviews)
Beautiful grounds and adorable, clean room. The bed was very comfortable. We'll stay here again next time!
Reviewed on Aug 11, 2026
A Cowslip's Belle Inn
CA $1,589
per person
Oct 1 - Oct 5
found 18 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Medford (MFR)
9.6/10 Exceptional! (48 reviews)
The Cowslips Belle Inn is amazing! Just a few short blocks from the Oregon Shakespeare Festival, many fine eateries and downtown Ashland. The grounds are superb with well tended landscaping, cozy seating areas and a wonderful koi pond. An off street parking area just for guests is excellent. The hosts were very gracious and friendly, personally greeting us and showing us our suite. The suite is beautifully decorated and very cozy with all the amenities that one might need. The notebook with restaurant recommendations, outlines of all the possibilities of things to do and entertainments in the area plus bios on all 3 hosts is a real plus. And the price is excellent for this wonder! Would highly recommend this Inn for a short or long stay in Southern Oregon.
Reviewed on Aug 7, 2026
Where to stay in Ashland
Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Historic Downtown District
4 out of top 10 points of interest in this area
If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.
Siskiyou-Hargadine Historic District
1 out of top 10 points of interest in this area
While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.
Historic Railroad District
Historic Railroad District might not have many top sights, but Allen Elizabethan Theatre and Thomas Theatre are two attractions nearby that you can check out.
Skidmore Academy Historic District
Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Thomas Theatre are two attractions nearby that you can check out.
Ready to book your vacation to Ashland?
Ashland Hotel Deals
Comfort Inn & Suites Ashland
434 S. Valley View Rd. Ashland OR
Fully refundable
CA $154
CA $156 total
Aug 31 - Sep 1
includes taxes & fees
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
CA $166
CA $199 total
Sep 7 - Sep 8
includes taxes & fees
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
CA $125
CA $140 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (1,412 reviews)
"You only get room service every 3 days so stinking garbage is left in room and you want towels need to pick up at front desk. Smoke detector in room flash green all night-not just little tiny light but entire unit. Also microwave made noises when in use that made you think it was going to ..."
Reviewed on Aug 17, 2026
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
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.
Photo by Shannon Willitts
Lithia Park
9.6/10 (1,250 reviews)
Explore the great outdoors at Lithia Park, a lovely green space in Ashland. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.
Mount Ashland Ski Area
8.6/10 (228 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.
Howard Prairie Lake
8.4/10 (33 reviews)
Commune with nature and explore the great outdoors at Howard Prairie Lake during your travels in Ashland. While in this family-friendly area, you can savor the top-notch restaurants.
Emigrant Lake
8.4/10 (70 reviews)
Commune with nature and explore the great outdoors at Emigrant Lake during your travels in Ashland. Experience the entertainment choices and lively festivals in this family-friendly area.
Allen Elizabethan Theatre
9.4/10 (131 reviews)
You can enjoy a show at Allen Elizabethan Theatre during your stay in Ashland. Wander around the area's picturesque gardens or experience its acclaimed theater scene.
Oregon Cabaret Theatre
9.0/10 (144 reviews)
You can make plans for a show at Oregon Cabaret Theatre during your trip to Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
Thomas Theatre
9.4/10 (144 reviews)
You can get tickets for a performance at Thomas Theatre on your trip to Ashland. Experience the area's entertainment choices and lively festivals.
What to do in Ashland
The Cultural Heart of Ashland: A Self-Guided Audio Tour
CA $14
per adult
Frequently asked questions
How much does an Ashland vacation package cost?
You can pick up a vacation package to this destination from CA $1,152 on Expedia. But how much your vacation to Ashland costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Ashland?
December, January and February are great times to search for cheap Ashland vacation packages. Travelling in quieter months means you'll typically find better prices on flights and hotels.
How many days is enough for Ashland?
Dedicate around 2 days for your Ashland vacation if you're hoping to discover all that makes this place special. Wander around key neighbourhoods, including Siskiyou-Hargadine Historic District and Historic Railroad District. Then check out top sights like Oregon Cabaret Theatre and Thomas Theatre. With a clever itinerary, you'll be kept busy with room for some me-time too. Want to venture beyond Ashland? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Ashland?
Well known for its cafes, cycling and hiking, an Ashland vacation is a hit with all types of travellers. Be sure to check out major sights like Oregon Shakespeare Festival and Lithia Park, and consider renting a set of wheels for day trips to discover even more.
How to find the best Ashland package deals?
Bagging a cheap Ashland package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can customize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most economical Ashland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Ashland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and accommodations separately. Better still, you can tailor your Ashland escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Ashland?
If you're considering an impromptu Ashland getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Ashland?
- Pick your travel dates: The things you'd like to do in Ashland and your favourite season can help you decide when to get away.
- Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Ashland.
- Decide your trip length: Consider how much time you want to spend exploring Ashland. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
- Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the right Ashland vacation package for you.
Explore a world of travel with Expedia
- Hotels with Balconies in Medford
- Cheap Hotels in Medford
- Shilo Inn Hotels in Ashland
- Prospero's Flagship Inn
- City Center Medford Hotels
- B&B in Ashland
- La Bella Vista. Close to downtown & shopping, public transportation.
- Clarion Pointe Medford
- Timbers INN and Suites
- Callahan's Mountain Lodge
- Anne Hathaway House
- Ashland Springs Hotel
- Luxury Hotels in Medford
- A sweet home away from your home
- Motel 6 Hotels in Ashland
- Ashland Hills Hotel & Suites
- Lithia Springs Resort
- Custom Ashland Home with Fantastic Mountain Views
- Ashland Hotels
- Historic Railroad District Hotels
- Rv Parks in Medford
- Stratford Inn
- #33 The Cabins at Hyatt Lake
- Serenity
- The Bard's Inn
- Hotels with a Pool in Medford
- Oak Street Cottages
- Motels in Medford
- Best Western Windsor Inn
- Best Western Hotels in Medford
- Lgbt Friendly Hotels in Ashland
- Lodge Room 7 at Green Springs Inn
- 5 Star Hotels in Medford
- Cheap Hotels in Ashland
- Hotels near Rogue Valley Intl.
- 4 Star Hotels in Medford
- Apartments in Ashland
- Abigail’s Bed & Breakfast Inn
- Hotels with Free Airport Shuttle in Medford
- Oceanfront Hotels in Ashland
- Fairfield Inn & Suites by Marriott Medford
- Historic Hotels in Medford
- Modern Farmhouse on Emigrant Creek
- Hilton Hotels in Ashland
- Pet-Friendly Hotels in Ashland
- Palm Cottages
- Ashland Street Inn
- The City Center Motel
- Pet-Friendly Hotels in Medford
- Medford Hotels
- Flights from Minneapolis (MSP) to Ashland (AHM)
- Flights from Detroit (DTW) to Ashland (AHM)
- Flights from Saskatoon (YXE) to Medford (MFR)
- Flights from Edmonton (YEG) to Medford (MFR)
- Flights from Portland (PDX) to Medford (MFR)
- Flights from Calgary (YYC) to Medford (MFR)
- Flights from Winnipeg (YWG) to Medford (MFR)
- Flights from Las Vegas (LAS) to Ashland (AHM)
- Flights from Oakland (OAK) to Ashland (AHM)
- Flights from Detroit (DTW) to Medford (MFR)
- Flights from Montreal (YUL) to Medford (MFR)
- Flights from Bellingham (BLI) to Medford (MFR)
- Flights from Toronto (YYZ) to Ashland (AHM)
- Flights from Seattle (SEA) to Ashland (AHM)
- Flights from Seattle (SEA) to Medford (MFR)
- Flights from New York (JFK) to Ashland (AHM)
- Flights from Winnipeg (YWG) to Ashland (AHM)
- Flights from Bangkok (BKK) to Ashland (AHM)
- Flights from Ottawa (YOW) to Medford (MFR)
- Flights from Denver (DEN) to Ashland (AHM)
- Flights from Chicago (ORD) to Ashland (AHM)
- Flights from Vancouver (YVR) to Medford (MFR)
- Flights from Tampa (TPA) to Ashland (AHM)
- Flights to Medford
- Flights from Ontario Intl. Airport (ONT) to Ashland (AHM)
- Flights from Amsterdam (AMS) to Ashland (AHM)
- Flights to Ashland
- Flights from Zürich (ZRH) to Ashland (AHM)
- Flights from San Francisco (SFO) to Medford (MFR)
- Flights from Buffalo (BUF) to Medford (MFR)
- Flights from Orange County (SNA) to Ashland (AHM)
- Flights from San Antonio (SAT) to Ashland (AHM)
- Flights from Kelowna (YLW) to Medford (MFR)
- Flights from Toronto (YYZ) to Medford (MFR)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
