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Ashland Vacation Packages

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Ashland Flight + Hotel Packages

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

Wine Country Inn

3 out of 5
Price was $872, price is now $772 per person
$772
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Art Presence Art Center and Quady North are located nearby.

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $1,199, price is now $994 per person
$994
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Book a stay at this luxury B&B in Central Point. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Jacksonville Cemetery and Art Presence Art Center are located nearby.
A converted estate that oozes with characters and charms in a beautiful surroundings, we were very happy to have found this place. The whole suit is spacious, bedroom and a separate living room. All the rooms have lots of windows that look out to the beautiful vineyard. The owners were relaxed and friendly. Highly recommend to stay for more than one day to relax and enjoy the wine and soak in the surroundings.

Reviewed on Sep 23, 2026

Winchester Inn

Winchester Inn

3.5 out of 5
Price was $1,082, price is now $937 per person
$937
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this inn in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Oregon Shakespeare Festival and Oregon Cabaret Theatre are located nearby.
The property is very charming, and comfortable with beautiful gardens and outdoor spaces. The breakfast choices were delicious and dinner was also exceptional. Staff is very warm, friendly and helpful. I recommend highly.

Reviewed on Sep 21, 2026

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $947, price is now $849 per person
$849
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oregon Shakespeare Festival and Weisinger Family Winery are located nearby.
Room was overlooking parking lot but was quiet.Nice part of town.

Reviewed on Sep 22, 2026

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Price was $1,060, price is now $952 per person
$952
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oregon Shakespeare Festival and Allen Elizabethan Theatre are located nearby.

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $1,000, price is now $902 per person
$902
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Book a stay at this golf hotel in Medford. Enjoy free breakfast, free parking, and a casino. Our guests praise the breakfast and the pool in our reviews. Popular attractions Ko-Kwel Casino Resort Medford and Bear Creek Golf Center are located nearby.

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Price was $1,022, price is now $927 per person
$927
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Oregon Shakespeare Festival and Ashland Library are located nearby.

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
Price was $956, price is now $870 per person
$870
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Oregon Shakespeare Festival and Allen Elizabethan Theatre are located nearby.
There should be more effort made for the continental breakfast. The only healthy items were apples and bananas. Junk food muffins and packaged high sugar cereals aren’t nourishing.

Reviewed on Sep 24, 2026

Ashland Vacation Packages 3-4 Night Stays

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

Wine Country Inn

3 out of 5
Price was $872, price is now $772 per person
$772
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $1,199, price is now $994 per person
$994
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Winchester Inn

Winchester Inn

3.5 out of 5
Historic Downtown District
Price was $1,082, price is now $937 per person
$937
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $947, price is now $849 per person
$849
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)

Ashland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Medford by IHG

Holiday Inn Express & Suites Medford by IHG

2.5 out of 5
Price was $540, price is now $530 per person
$530
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $809, price is now $740 per person
$740
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Fairfield Inn & Suites by Marriott Medford

Fairfield Inn & Suites by Marriott Medford

3 out of 5
Price was $600, price is now $597 per person
$597
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Bargain Flight
Mon, Nov 23 - Sat, Dec 5
SAN
San Diego Intl.
MFR
Rogue Valley Intl.
$219 Roundtrip, found 3 hours ago
$219
Roundtrip
found 3 hours ago
Select Bargain Flight flight, departing Mon, Nov 23 from San Diego Intl. to Rogue Valley Intl., returning Sat, Dec 5, priced at $219 found 3 hours ago
Alaska Airlines
Fri, Nov 6 - Wed, Nov 11
PDX
Portland Intl.
MFR
Rogue Valley Intl.
$246 Roundtrip, found 20 hours ago
$246
Roundtrip
found 20 hours ago
Select Alaska Airlines flight, departing Fri, Nov 6 from Portland Intl. to Rogue Valley Intl., returning Wed, Nov 11, priced at $246 found 20 hours ago
Bargain Flight
Sat, Oct 3 - Tue, Oct 6
SFO
San Francisco Intl.
MFR
Rogue Valley Intl.
$289 Roundtrip, found 6 days ago
$289
Roundtrip
found 6 days ago
Select Bargain Flight flight, departing Sat, Oct 3 from San Francisco Intl. to Rogue Valley Intl., returning Tue, Oct 6, priced at $289 found 6 days ago
Bargain Flight
Thu, Dec 17 - Fri, Dec 25
DEN
Denver Intl.
MFR
Rogue Valley Intl.
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Thu, Dec 17 from Denver Intl. to Rogue Valley Intl., returning Fri, Dec 25, priced at $315 found 2 days ago