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Trail Vacation Packages

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Trail Flight + Hotel Packages

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

Ashland Hills Hotel & Suites

3 out of 5
Price was $755, price is now $678 per person
$678
per person
Oct 16 - Oct 20
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.
This was a very nice stop. Close to many things.

Reviewed on Aug 28, 2026

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Price was $1,059, price is now $883 per person
$883
per person
Oct 16 - Oct 20
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.
A beautiful, comfortable and very convenient place to stay.

Reviewed on Aug 24, 2026

Winchester Inn

Winchester Inn

3.5 out of 5
Price was $1,137, price is now $957 per person
$957
per person
Oct 16 - Oct 20
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.
Everything was perfect

Reviewed on Aug 6, 2026

Hanna's House by WanderLodges

Hanna's House by WanderLodges

4 out of 5
Price was $1,029, price is now $900 per person
$900
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip 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

Meadowsweet Farm by WanderLodges

Meadowsweet Farm by WanderLodges

3 out of 5
Price was $1,685, price is now $1,516 per person
$1,516
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this vacation home in Medford. Enjoy free WiFi, free parking, and a garden. Popular attractions Oregon Shakespeare Festival and Paschal Winery are located nearby.

The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges

4 out of 5
Price was $1,330, price is now $1,198 per person
$1,198
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this vacation home in Ashland. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Oregon Shakespeare Festival and North Mountain Park are located nearby.
This place was a 10/10! Made a big breakfast for my friends. Grocery store very close. I will be returning!

Reviewed on Sep 27, 2025

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio

3 out of 5
Price was $1,328, price is now $1,203 per person
$1,203
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Price was $776, price is now $703 per person
$703
per person
Oct 16 - Oct 20
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 place was cute. Room was really nice and bed was comfy. Close to downtown. Would stay there again.

Reviewed on Aug 13, 2026

Trail Vacation Packages 3-4 Night Stays

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

Ashland Hills Hotel & Suites

3 out of 5
Price was $755, price is now $678 per person
$678
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $1,059, price is now $883 per person
$883
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 $1,137, price is now $957 per person
$957
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 $1,029, price is now $900 per person
$900
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)

Trail Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
TownePlace Suites by Marriott Medford

TownePlace Suites by Marriott Medford

3 out of 5
Price was $730, price is now $649 per person
$649
per person
Oct 10 - Oct 17
found 5 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Save 100% on your flight
Price was $1,881, price is now $1,527 per person
$1,527
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Wine Country Inn

Wine Country Inn

3 out of 5
Price was $831, price is now $745 per person
$745
per person
Oct 10 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
Riverfront Lodging

Riverfront Lodging

2.5 out of 5
Price was $782, price is now $717 per person
$717
per person
Oct 10 - Oct 17
found 3 hours ago
Roundtrip non-stop 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
Tue, Sep 15 - Tue, Sep 22
LAS
Harry Reid Intl.
MFR
Rogue Valley Intl.
$257 Roundtrip, found 18 hours ago
$257
Roundtrip
found 18 hours ago
Select Bargain Flight flight, departing Tue, Sep 15 from Harry Reid Intl. to Rogue Valley Intl., returning Tue, Sep 22, priced at $257 found 18 hours ago
Alaska Airlines
Sat, Sep 26 - Mon, Sep 28
SFO
San Francisco Intl.
MFR
Rogue Valley Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Sat, Sep 26 from San Francisco Intl. to Rogue Valley Intl., returning Mon, Sep 28, priced at $257 found 2 days ago
Bargain Flight
Fri, Dec 4 - Sun, Dec 6
PHX
Sky Harbor Intl.
MFR
Rogue Valley Intl.
$264 Roundtrip, found 1 day ago
$264
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Dec 4 from Sky Harbor Intl. to Rogue Valley Intl., returning Sun, Dec 6, priced at $264 found 1 day ago
Bargain Flight
Sat, Sep 12 - Tue, Sep 15
LAX
Los Angeles Intl.
MFR
Rogue Valley Intl.
$265 Roundtrip, found 5 days ago
$265
Roundtrip
found 5 days 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 5 days ago