Jackson County Vacations & Trips from $824

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Your Jackson County Vacation

Embark on your next big adventure with a Jackson County vacation package, and leave knowing all the details are already organized. Plus with the ability to tailor your getaway, it'll be one you won't forget. A trip to Jackson County wouldn't be complete without experiencing some of its most renowned cities, starting with Ashland. A couple of the most popular attractions here include Oregon Shakespeare Festival and Lithia Park. Prospect is another favorite city with Jackson County travelers. Visitors to this exciting city enjoy Mill Creek Falls and Joseph H Stewart State Park. Whether you plan to travel for a couple of days or a couple of weeks, Expedia are here to help you organize your next dream Jackson County vacation.

Top destinations in Jackson County

A deer on a road with vegetation on the sides.

Ashland

Ashland
A mountainous landscape with rocky terrain, dense forests, and a clear sky with scattered clouds.

Prospect

Prospect
A street lined with buildings, trees, and traffic lights.

Medford

Medford
A field of crops with a hill and mountain in the background.

Central Point

Central Point
A hat display in a store with various hats hanging on a rack.

Jacksonville

Jacksonville
A bridge over a river with trees and a clear sky.

Shady Cove

Shady Cove
A mountainous landscape with a river, green fields, and a prominent snow-capped peak in the background.

White City

White City
A group of people in a yellow inflatable raft on a river.

Rogue River

Rogue River

The Latest Jackson County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

$824
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
8.8/10 Excellent! (1,541 reviews)
Kubli Haus

Kubli Haus

$1,412
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
No reviews
Wine Country Inn

Wine Country Inn

$946
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.4/10 Exceptional! (1,004 reviews)
Great location. Walking distance to Jacksonville. Easy parking. Pleasant staff. Clean toom.

Reviewed on Oct 11, 2026

Winchester Inn

Winchester Inn

Historic Downtown District
$1,019
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (288 reviews)
Amazing breakfasts, friendly staff, best location

Reviewed on Oct 10, 2026

The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges

$1,480
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
10/10 Exceptional! (7 reviews)

Find the Best Jackson County Vacation Packages

Jackson County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rogue Valley Intl. Airport (MFR)
Top Sights
Lithia Park, Howard Prairie Lake and Emigrant Lake

Jackson County Hotel Deals

Red Lion Hotel Rogue Regency Medford Airport

Red Lion Hotel Rogue Regency Medford Airport

2300 Biddle Rd Medford OR
Fully refundableReserve now, pay when you stay
$103 nightly
$115 total
Oct 14 - Oct 15
Total with taxes and fees
Red Lion Hotel Rogue Regency Medford Airport
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

2399 S Pacific Hwy Medford OR
Fully refundableReserve now, pay when you stay
$164 nightly
$183 total
Oct 18 - Oct 19
Total with taxes and fees
Compass by Margaritaville in Medford
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
$121 nightly
$135 total
Nov 5 - Nov 6
Total with taxes and fees
Ashland Hills Hotel & Suites
See all 792 properties in Jackson County
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 Jackson County 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

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

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 entertainment choices in this family-friendly area.
See properties
A snowy forest with tall evergreen trees covered in snow.

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 entertainment choices in this walkable area.
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Lithia & Driveway Fields

8.4/10 (91 reviews)
Catch an event at Lithia & Driveway Fields during your trip to Medford. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
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The Expo

8.0/10 (122 reviews)
Enjoy an outing to The Expo during your stay in Central Point. While you're here, you can savor the top-notch restaurants.
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Rogue Valley Mall

8.2/10 (554 reviews)
You can search for that perfect souvenir at Rogue Valley Mall during your visit to Medford. Wander the area's picturesque gardens or simply enjoy one of its top-notch restaurants.
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Centennial Golf Club

7.8/10 (9 reviews)
Enjoy a round of golf in Medford at Centennial Golf Club. Discover the area's top-notch restaurants and its acclaimed theater scene.
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Rogue Valley Country Club

8.4/10 (72 reviews)
Enjoy a round of golf in Medford at Rogue Valley Country Club. Wander around the area's picturesque gardens or experience its acclaimed theater scene.
See properties

What to do in Jackson County

Crater Lake National Park Self-Guided Audio Tour

Crater Lake National Park Self-Guided Audio Tour

$19
per traveler
Crater Lake National Park Self-Guided Audio Tour
Self Guided Audio Tour Bundle US Pacific Coastline

Self Guided Audio Tour Bundle US Pacific Coastline

$110
per traveler
Self Guided Audio Tour Bundle US Pacific Coastline
See all activities in Jackson County
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.