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Southern Oregon Vacation Packages

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Southern Oregon 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 $532, price is now $477 per person
$477
per person
Oct 20 - Oct 23
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Price was $641, price is now $560 per person
$560
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop 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.

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $610, price is now $534 per person
$534
per person
Oct 20 - Oct 23
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.
Beautiful grounds and adorable, clean room. The bed was very comfortable. We'll stay here again next time!

Reviewed on Aug 11, 2026

Winchester Inn

Winchester Inn

3.5 out of 5
Price was $656, price is now $580 per person
$580
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop 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.
Everything was perfect

Reviewed on Aug 6, 2026

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio

3 out of 5
Price was $985, price is now $888 per person
$888
per person
Oct 20 - Oct 23
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Medford (MFR)
Stay at this vacation home in Medford. Enjoy free WiFi, free parking, and a sauna. Popular attractions Blackbird Statue and Medford Carnegie Library are located nearby.

Hanna's House by WanderLodges

Hanna's House by WanderLodges

4 out of 5
Price was $665, price is now $605 per person
$605
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
Book a stay at this business-friendly vacation home in Ashland. Enjoy free WiFi, free parking, and a garden. Popular attractions Oregon Shakespeare Festival and Ashland Library are located nearby.
Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private.

Reviewed on Aug 2, 2026

Starwood Sanctuary

Starwood Sanctuary

3 out of 5
Price was $768, price is now $698 per person
$698
per person
Oct 20 - Oct 23
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Medford (MFR)
Stay at this vacation home in Medford. Enjoy free WiFi, free parking, and a garden. Popular attractions Rogue Karting and Medford Railroad Park are located nearby.
I was able to have early check in. The private bathroom off the main room was tiny. Coffee and cocoa were nice. The beds were comfy but the accent lights didn’t work and the shampoo dispenser was broken. Price and location were nice.. may book again.. spider webs outside 🤔😊

Reviewed on Aug 13, 2026

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $582, price is now $531 per person
$531
per person
Oct 20 - Oct 23
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) 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.

Southern Oregon Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $610, price is now $534 per person
$534
per person
Oct 20 - Oct 23
found 3 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Medford (MFR)
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $993, price is now $820 per person
$820
per person
Oct 16 - Oct 20
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 $1,097, price is now $914 per person
$914
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Hanna's House by WanderLodges

Hanna's House by WanderLodges

4 out of 5
Historic Railroad District
Price was $989, price is now $858 per person
$858
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)

Southern Oregon Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
Price was $903, price is now $837 per person
$837
per person
Sep 23 - Sep 30
just found
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $992, price is now $894 per person
$894
per person
Sep 23 - Sep 30
just found
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)

Top Flight Deals

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

Bargain Flight
Tue, Oct 27 - Wed, Oct 28
SAN
San Diego Intl.
MFR
Rogue Valley Intl.
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Oct 27 from San Diego Intl. to Rogue Valley Intl., returning Wed, Oct 28, priced at $212 found 3 days ago
Delta
Fri, Nov 6 - Wed, Nov 11
PDX
Portland Intl.
MFR
Rogue Valley Intl.
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Nov 6 from Portland Intl. to Rogue Valley Intl., returning Wed, Nov 11, priced at $247 found 3 days ago
Bargain Flight
Sat, Sep 12 - Tue, Sep 15
LAX
Los Angeles Intl.
MFR
Rogue Valley Intl.
$265 Roundtrip, found 19 hours ago
$265
Roundtrip
found 19 hours ago
Select Bargain Flight flight, departing Sat, Sep 12 from Los Angeles Intl. to Rogue Valley Intl., returning Tue, Sep 15, priced at $265 found 19 hours ago
American Airlines
Wed, Oct 21 - Sat, Oct 31
CLD
McClellan-Palomar
MFR
Rogue Valley Intl.
$319 Roundtrip, found 3 days ago
$319
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Oct 21 from McClellan-Palomar to Rogue Valley Intl., returning Sat, Oct 31, priced at $319 found 3 days ago