Ashland Vacation Packages 2026 from $677

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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.

The Latest Ashland vacation packages

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

Wine Country Inn

$677

per person

Nov 6 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Grand Rapids (GRR) to Medford (MFR)

9.4/10 Exceptional! (1,004 reviews)

This is a great place to stay in Jacksonville! Huge king fireplace suite!

Reviewed on Oct 6, 2026

Out 'N' About Treehouse Treesort

$1,119

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Grand Rapids (GRR) to Medford (MFR)

9.4/10 Exceptional! (34 reviews)

The room was advertised as up to 4 people. It was so small there was only a small path from the door to the bed. No other walking space. There were piles of junk at the bottom of my treehouse, including old boards and tools. It was unsightly and could be a safety issue for children playing. There was old equipment everywhere and an old junk car in the zip line area. It was just an okay stay.

Reviewed on Sep 16, 2026

Compass by Margaritaville in Medford

$931

per person

Nov 6 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Grand Rapids (GRR) to Medford (MFR)

9.6/10 Exceptional! (1,152 reviews)

Hummingbird Estate Wine & Suites

$1,380

per person

Nov 6 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Grand Rapids (GRR) to Medford (MFR)

9.6/10 Exceptional! (188 reviews)

The ambience can’t be beat! In addition to finding the property spectacular, we enjoyed the complimentary wine flight.

Reviewed on Oct 6, 2026

Kubli Haus

$1,290

per person

Nov 6 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Grand Rapids (GRR) to Medford (MFR)

No reviews

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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

A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.

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.

A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

While visiting Siskiyou-Hargadine Historic District, you might make a stop by sights like Lithia Park and Ashland Library.

A rusted metal bridge in a forested area.

Historic Railroad District

Historic Railroad District might not have many top sights, but Oregon Cabaret Theatre and Allen Elizabethan Theatre are two attractions nearby that you can check out.

A town with buildings and trees in autumn colors, surrounded by mountains.

Skidmore Academy Historic District

Skidmore Academy Historic District might not have many top sights, but Allen Elizabethan Theatre and Oregon Shakespeare Festival are two attractions nearby that you can check out.

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.

Oregon Shakespeare Festival

9.2/10 (620 reviews)

At OSF, America's oldest repertory theater presents Shakespearean classics and bold new works across three venues. Reserve seats for evening performances and arrive early for the free outdoor Green Show entertainment.

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A wood duck standing on rocks with moss and greenery in the background.

Lithia Park

9.6/10 (1,250 reviews)

Stroll through Lithia Park's 93 acres of landscaped beauty alongside Ashland Creek. Discover Japanese gardens, duck ponds, and seasonal foliage while enjoying the serenity of this historic green space.

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A snowy forest with tall evergreen trees covered in snow.

Mount Ashland Ski Area

8.6/10 (228 reviews)

Southern Oregon's premier ski destination offers 44 trails across 240 acres of varied terrain. Enjoy twilight skiing on select evenings for a magical mountain experience under the stars.

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Emigrant Lake

8.4/10 (70 reviews)

Emigrant Lake offers warm waters and scenic views just five miles from Ashland, Oregon. Enjoy the thrilling 280-foot twin flume water slide during summer or camp beneath the stars in this recreational haven.

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Oregon Cabaret Theatre

9.0/10 (144 reviews)

Set in a restored 1911 mission-style church, Oregon Cabaret Theatre pairs professional musical performances with gourmet dining. Enjoy tiered seating with balcony views while savoring chef-prepared meals.

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Howard Prairie Lake

8.4/10 (33 reviews)

A pristine 1,990-acre reservoir in the Cascade Mountains, Howard Prairie Lake offers exceptional trout and bass fishing. Enjoy tranquil boating amid pine forests or unwind at the lakeside resort with mountain views.

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Allen Elizabethan Theatre

9.4/10 (131 reviews)

This open-air Elizabethan-style theater hosts the renowned Oregon Shakespeare Festival. Evening performances unfold beneath the stars, creating a magical atmosphere reminiscent of Shakespeare's era.

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Angus Bowmer Theatre

10.0/10 (11 reviews)

The heart of Oregon Shakespeare Festival, this intimate 600-seat venue places every audience member within 55 feet of the stage. Experience world-class performances where Shakespeare's words and contemporary works come alive.

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Ashland Hotel Deals

Ashland Hills Hotel & Suites

2525 Ashland St Ashland OR

Fully refundableReserve now, pay when you stay

$121 nightly

$135 total

Nov 2 - Nov 3

Total with taxes and fees

8.8/10 Excellent! (1,541 reviews)

"The room was very cleann and quiet."

Reviewed on Oct 6, 2026

Stratford Inn

555 Siskiyou Blvd Ashland OR

$73 nightly

$82 total

Nov 4 - Nov 5

Total with taxes and fees

9.4/10 Exceptional! (1,798 reviews)

"Reasonable value and probably as good as you can expect for this price range in this excellent location within walking distance of downtown , but I have to say it’s very dated. With 1950’s wallpaper, flooring, and furniture. Also the dim lighting, small windows and in-room a/c units. I was in a spacious ..."

Reviewed on Oct 6, 2026

Comfort Inn & Suites Ashland

434 S. Valley View Rd. Ashland OR

Fully refundable

$116 nightly

$118 total

Nov 2 - Nov 3

Total with taxes and fees

9/10 Wonderful! (1,040 reviews)

"The property was in excellent condition and very clean. Excellent rate!"

Reviewed on Oct 6, 2026

See all 724 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.

Find the Best Ashland Vacation Packages

Things to do in and around Ashland

Ashland, Oregon, is perfect for outdoor enthusiasts and adventure seekers, offering a blend of scenic beauty and cultural experiences. Visitors can enjoy activities like exploring the renowned Oregon Shakespeare Festival, engaging in wine tasting tours, and partaking in recreational adventures across beautiful landscapes. With opportunities for skiing and a vibrant arts scene, Ashland promises an unforgettable getaway filled with diverse experiences.

Shopping

Ashland offers a delightful shopping experience with unique shops and local treasures. For a bit of a drive, Rogue Valley Mall, 13 miles away, features various stores and entertainment. Additionally, explore Kharmic Creations, 15 miles away, or visit Rogue Creamery, located 16 miles from the city for delicious artisanal cheeses.

Recreation

Experience the vibrant culture at the Oregon Shakespeare Festival, where captivating performances ignite the spirit. Enjoy the romantic ambiance of the Allen Elizabethan Theatre, offering enchanting shows. Unwind at the Oregon Cabaret Theatre, where delightful entertainment creates a warm, family-friendly atmosphere, perfect for relaxation and joy.

Adventure

Mount Ashland Ski Area offers exhilarating skiing experiences with stunning mountain views, perfect for both beginners and seasoned skiers. For an adventurous ride, the Comer Ski Lift provides easy access to thrilling slopes. Explore the Bull Gap Lower Trailhead for scenic hiking amidst breathtaking landscapes and outdoor adventures.

Nightlife

A night in Ashland offers a vibrant atmosphere, from live performances at the Oregon Shakespeare Festival to cozy drinks at local pubs like the Ashland Springs Hotel. For a lively evening, check out the nightly events at the Ashland Elks Lodge or enjoy a relaxed vibe at Caldera Tap House.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Ashland

Ashland, Oregon, is a fantastic destination for outdoor enthusiasts and adventure seekers, featuring beautiful lakes, urban parks, and modern colleges. Visitors can explore the scenic Ashland Creek, enjoy skiing at the Mount Ashland Ski Area, and discover the charming culture of the city. With its array of attractions and activities, Ashland promises a memorable experience that combines nature, adventure, and local culture.

Southern Oregon University: Experience the vibrant city atmosphere at Southern Oregon University, where modern architecture meets a lively campus life. Explore the beautiful grounds and engage with local students, enjoying the energy that this educational hub brings to Ashland.
Lithia Park: Enjoy a family-friendly outdoor escape at Lithia Park, a sprawling urban park filled with serene walking paths, picnic areas, and picturesque gardens. It’s a perfect spot for relaxation and recreation, right in the heart of the city.
Howard Prairie Lake: Discover the romantic charm of Howard Prairie Lake, a stunning natural oasis featuring sandy beaches and breathtaking scenery. Ideal for outdoor enthusiasts, it offers opportunities for swimming, fishing, and picnicking amidst serene landscapes.

Best time to go to Ashland

The best time to visit Ashland is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. December is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	36.3°F (2.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
February	37.2°F (2.9°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	40.5°F (4.7°C)	Light Rain	Mostly Sunny	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	53.2°F (11.8°C)	Light Rain	Mostly Sunny	Average	Average
June	60.4°F (15.8°C)	No Rain	Mostly Sunny	Slightly High	Slightly High
July	69.3°F (20.7°C)	No Rain	Sunny	Slightly High	Slightly High
August	68.7°F (20.4°C)	No Rain	Sunny	Average	Slightly High
September	61.5°F (16.4°C)	No Rain	Sunny	Average	Average
October	51.1°F (10.6°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	40.8°F (4.9°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	34.7°F (1.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

Tips to save on your trip to Ashland

Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Ashland.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Ashland Essential Information

Language	English
Currency	U.S dollars
Closest Airport	Rogue Valley Intl. Airport (MFR)
Population	20,900
Max Temp Winter	45ºF
Max Temp Summer	80ºF
Top Sights	Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre

More vacations you might like

Frequently asked questions

What types of vacation packages are available in Ashland?

Ashland, known for its outdoor activities and romantic getaways, offers several types of vacation packages to suit different travel styles:

Budget-friendly: A select few hotels fall into the budget tier. Stratford Inn, rated 8.7 out of 10 by travelers, offers amenities like an indoor pool and free breakfast.
Pet-friendly: Callahan's Mountain Lodge, rated 8.1 out of 10 by travelers, welcomes pets and features a restaurant and game room, making it a comfortable stay for the whole family.
Breakfast-included: Abigail's Bed & Breakfast Inn, rated 9.9 out of 10 by travelers, provides free breakfast and a kitchen, perfect for a cozy start to your day.
Family-friendly: Arden Forest Inn, a 4-star property rated 9.1 out of 10 by travelers, is a strong choice for families with its family rooms and outdoor pool.
Romantic/Couples: McCall House Boutique Inn, a 4-star hotel rated 9.6 out of 10 by travelers, is ideal for couples, with travelers often praising its gorgeous rooms and wonderful staff.

How can I save money on a Ashland vacation package?

When you bundle, you can save up to 30%*. To save money on a Ashland package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

How much does an Ashland vacation package cost?

An Ashland vacation package typically costs around $800 per adult for a weekend trip. Lower-priced options start around $500 per adult, while premium packages can reach up to $1,850.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

How do I find cheap Ashland vacation package deals?

The cheapest Ashland vacation package deals can be as low as around $410 per adult for weekend trips. Separately, May typically has the lowest average monthly prices, around $1,070 per adult for a 4-day trip, with August following closely at around $1,100 per adult for a 5-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — most Ashland packages include some savings versus booking separately, typically around $25 per adult. Week-long trips can save even more, often around $55 per adult. Browse cheap vacation packages in Ashland on Expedia for current deals.*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.

What is the best time to go to Ashland?

The best time to go for an Ashland vacation package is typically from May through July. These months see the highest number of bookings, indicating favorable conditions for enjoying Ashland's outdoor activities and romantic appeal.For a more budget-friendly Ashland vacation, consider booking your trip in August or October, as these months tend to offer lower package prices.

What's included in an Ashland vacation package?

An Ashland vacation package lets you combine round-trip flights, a hotel stay, and a rental car. Many hotels here offer free breakfast, and some also provide airport shuttle service to and from Medford, OR (MFR-Rogue Valley Intl.). As an outdoor and nature destination, packages often place you near scenic views and adventure activities.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

What's the best vacation package for Ashland?

For a romantic Ashland vacation package, consider a stay at McCall House Boutique Inn, a 4-star property rated 9.6 out of 10 by travelers. This boutique inn, about a 5-minute walk from the Oregon Shakespeare Festival, is praised for its gorgeous rooms and wonderful staff, making it ideal for couples.Families can find a great Ashland vacation package with a stay at Arden Forest Inn, a 4-star hotel rated 9.1 out of 10 by travelers. It offers family rooms and an outdoor pool, with travelers often highlighting its spacious rooms and great location about a 10-minute walk from the Oregon Shakespeare Festival.Travelers seeking a value-focused Ashland vacation package might consider Stratford Inn, rated 8.7 out of 10 by travelers. This hotel, costing around $130 per night and about a 10-minute walk from the Oregon Shakespeare Festival, is a favorite for its indoor pool and comfy beds, with travelers noting the well-done breakfast.*Package availability and prices may change depending on dates and demand.

Is Ashland a good choice for a family vacation package?

Ashland can be a good choice for family vacation packages, offering a mix of outdoor activities and family-friendly accommodations. While a select few bookings are family trips, several hotels cater to families with useful amenities.For instance, Ashland Hills Hotel & Suites, rated 8.2 out of 10 by travelers, is about 3 miles from the Oregon Shakespeare Festival and features an outdoor pool and a playground, making it a comfortable base for families.Families can also enjoy attractions like Lithia Park, which has duck ponds and playgrounds about a 10-minute walk from central Ashland. For water activities, Emigrant Lake, about 11 miles from central Ashland, offers boating, lake swimming, and water slides.

Which Ashland vacation packages include a mountain view?

About half of Ashland vacation packages include hotels with mountain views. McCall House Boutique Inn, a 4-star property rated 9.6 out of 10 by travelers, offers mountain-view room options and is about a 5-minute walk from Oregon Shakespeare Festival; travelers frequently praise its gorgeous rooms and wonderful staff. Another option is Callahan's Mountain Lodge, rated 8.1 out of 10, which is about 10 miles from Oregon Shakespeare Festival and is noted for its incredible food and beautiful location. Keep in mind that mountain views depend on the specific room and rate booked within your Ashland vacation package.

What is the best time to book an Ashland vacation package?

Book your Ashland vacation package around 5 weeks in advance. This gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 2 and 11 weeks out.May, June, and July are the most popular months for Ashland packages, so booking earlier is advisable if you're traveling during these times.

What are the top things to do in Ashland?

An Ashland vacation offers a blend of cultural experiences and outdoor adventures in a scenic setting:Browse and book things to do in Ashland on Expedia.

How many days do you need for an Ashland vacation?

Most Ashland vacation packages last around 4 days, which is a good amount of time to explore the area's highlights. This duration allows you to enjoy a performance at the Oregon Shakespeare Festival, wander through Lithia Park, and visit a local spot like Weisinger Family Winery.While nearly a third of travelers choose week-long trips, about half of all bookings are for weekend trips, showing that a shorter stay is also a popular option for a focused Ashland vacation.

Is Ashland a good destination for a weekend vacation?

Yes, Ashland is a good destination for a weekend vacation, with about half of all package bookings being for 1 to 3 days. A short trip allows you to focus on key attractions like attending a performance at the Oregon Shakespeare Festival or exploring the scenic Lithia Park. While the typical Ashland vacation package lasts around 4 days, a weekend getaway still offers a fulfilling experience.

Do you need to rent a car in Ashland, or is public transport enough?

For an Ashland vacation package, a rental car offers the most flexibility, especially for exploring the outdoor and nature attractions outside the immediate town center. While many hotels and B&Bs are within walking distance of central Ashland, and bike lanes are available, public bus service operates with limited hours and does not run on weekends.Having a car makes it easier to reach destinations like Mount Ashland Ski Area or Emigrant Lake. Parking can be scarce in downtown Ashland during summer evenings, but a car allows you to venture further afield. For arrivals, Medford, OR (MFR-Rogue Valley Intl.) Airport is the primary gateway for Ashland vacation packages with flights.

Are Ashland vacation package hotels conveniently located?

Ashland vacation package hotels offer a range of convenient locations, with many properties situated within easy reach of central Ashland and its main attractions.For example, the 4-star McCall House Boutique Inn, rated 9.6 out of 10, is about a 5-minute walk from central Ashland. Similarly, the 3.5-star Winchester Inn, rated 9.3 out of 10, is also about a 5-minute walk from the center. If you prefer to be slightly outside the immediate downtown area, Ashland Motel - Oregon, rated 8.1 out of 10, is about 1 mile from central Ashland. This variety allows you to choose a stay that best fits your preference for walkability or a short drive to explore the area.

Can I change or cancel my Ashland vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Ashland vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Ashland vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Ashland vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Ashland?

To find last-minute vacation packages to Ashland, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Ashland vacation packages?

Free cancellation on a Ashland vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Ashland vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Ashland getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Ashland vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

Ashland Vacation Rentals

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Ashland Vacations from $677

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Ashland Vacation

The Latest Ashland vacation packages

Wine Country Inn

Out 'N' About Treehouse Treesort

Compass by Margaritaville in Medford

Hummingbird Estate Wine & Suites

Kubli Haus

Where to stay in Ashland

Historic Downtown District

Siskiyou-Hargadine Historic District

Historic Railroad District

Skidmore Academy Historic District

Stay near popular Ashland attractions

Oregon Shakespeare Festival

Lithia Park

Mount Ashland Ski Area

Emigrant Lake

Oregon Cabaret Theatre

Howard Prairie Lake

Allen Elizabethan Theatre

Angus Bowmer Theatre

Ashland Hotel Deals

Ashland Hills Hotel & Suites

Stratford Inn

Comfort Inn & Suites Ashland

Find the Best Ashland Vacation Packages

Things to do in and around Ashland

Find the best attractions in Ashland

Best time to go to Ashland

Tips to save on your trip to Ashland

Ashland Essential Information

More vacations you might like

Frequently asked questions

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