Siskiyou-Hargadine Historic District Vacations from $442

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Your Siskiyou-Hargadine Historic District Vacation

Booking a Siskiyou-Hargadine Historic District vacation package is a superb way to know the ins and outs of this neighborhood. From its must-visit places to its little-known delights, you won't be short of new adventures. When it's time to take in the sights, you'll find plenty of awesome attractions nearby including Southern Oregon University, Oregon Shakespeare Festival and Lithia Park. Visit one, two or all during your trip to Siskiyou-Hargadine Historic District. Expedia can help turn your dream Siskiyou-Hargadine Historic District vacation into reality, whatever your budget or travel plans.

The Latest Siskiyou-Hargadine Historic District Vacation Packages

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

Wine Country Inn

3 out of 5
Price was $573, price is now $442 per person
$442
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.4/10 Exceptional! (1,006 reviews)
Great place to stay with or without a dog. Loved the location. Very clean. Highly recommend

Reviewed on Nov 6, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $898, price is now $643 per person
$643
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.2/10 Wonderful! (572 reviews)
Location was very convenient to walking everywhere. Breakfast was fresh and delicious.

Reviewed on Oct 12, 2025

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $733, price is now $577 per person
$577
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.6/10 Exceptional! (138 reviews)
Absolutely lovely place to spend time, relax and enjoy the beautiful property and views. Highly recommend.

Reviewed on Oct 18, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $707, price is now $565 per person
$565
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.6/10 Exceptional! (1,013 reviews)
Staff are great. Rooms are clean. Great breakfast.

Reviewed on Oct 26, 2025

Paschal Winery

Paschal Winery

4.5 out of 5
Price was $654, price is now $527 per person
$527
per person
Dec 19 - Dec 23
found 7 hours ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
9.6/10 Exceptional! (13 reviews)
It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.

Reviewed on May 3, 2025

Where to stay in Siskiyou-Hargadine Historic District

Find the best Siskiyou-Hargadine Historic District areas and neighborhoods for the activities you enjoy most. Learn more about Siskiyou-Hargadine Historic District
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Historic Downtown District

4 out of top 10 points of interest in this area
5/5(133 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

Find hotels in Historic Downtown District

Siskiyou-Hargadine Historic District Hotel Deals

Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd, Ashland, OR
Fully refundable
$90 nightly
The price is $100 total per night from Dec 1 to Dec 2
$100 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (1,574 reviews)
This was our first time staying here despite coming to Ashland for decades, and we don't feel like we have been missing out on much. The best feature here is the walking distance (in nice weather) to downtown. It was noisy in all ways: thin walls, street traffic, loud guests, etc. We would not stay ...

Reviewed on Nov 3, 2025

Stratford Inn
Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
2300 Biddle Rd, Medford, OR
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $118 total per night from Nov 13 to Nov 14
$118 total
Nov 13 - Nov 14
Total with taxes and fees
8.8/10 Excellent! (2,574 reviews)
Friendly check in staff

Reviewed on Nov 5, 2025

Rogue Regency Inn and Suites
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 out of 5
1193 Siskiyou Blvd, Ashland, OR
Fully refundableReserve now, pay when you stay
$45 nightly
The price is $50 total per night from Nov 20 to Nov 21
$50 total
Nov 20 - Nov 21
Total with taxes and fees
8.6/10 Excellent! (1,126 reviews)
Easy check in, convenient location.

Reviewed on Nov 1, 2025

Flagship Inn of Ashland
See all 676 properties in Siskiyou-Hargadine Historic District
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.
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Discover the most popular places to visit in Siskiyou-Hargadine Historic District

Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays. The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland. #WeekendGetaway

Oregon Shakespeare Festival

4.5/5(265 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.

Oregon Shakespeare Festival
Being the tallest peak in the Siskiyou Mountains, Mt. Ashland offers excellent panoramic views, year round. The ski resort is relatively small, but the runs are steep and a few have cornice drops and chutes. It's a half hour drive from the town of Ashland in good weather. This photo was taken pre-season near the peak after a short yet strenuous ascent. #WeekendGetaway

Mount Ashland Ski Area

4/5(70 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.

Mount Ashland Ski Area

Southern Oregon University

4.5/5(146 reviews)

Enjoy the collegiate vibe at Southern Oregon University as part of your travels around Ashland. Experience the area's entertainment choices and acclaimed theater scene.

Southern Oregon University

Things to do

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

Ashland Team Trivia Hunt: New 2024 Mobile Game App!

$42
per adult
Ashland Team Trivia Hunt: New 2024 Mobile Game App!
Salem Puzzling Adventure

Ashland Puzzling Adventure

$35
per traveler
Ashland Puzzling Adventure
See all activities in Ashland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.