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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.
Lithia Springs Resort

Lithia Springs Resort

3 out of 5
Price was $526, price is now $436 per person
$436
per person
Nov 5 - Nov 10
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this B&B 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 Allen Elizabethan Theatre are located nearby.
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Reviewed on Sep 18, 2026

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $756, price is now $560 per person
$560
per person
Nov 5 - Nov 10
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.
Very cute winery and we had tickets for free drinks because we were staying in the rooms. Clean but the air conditioning did leak onto the floor both nights and the outlet in the bathroom did not work making it difficult to get ready. Would stay again.. just needs a little updating.

Reviewed on Sep 16, 2026

Winchester Inn

Winchester Inn

3.5 out of 5
Price was $811, price is now $618 per person
$618
per person
Nov 5 - Nov 10
found 2 hours 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.
Our stay at the Winchester Inn was very pleasant and enjoyable. The complimentary made to order breakfast was delicious, and the room was very comfortable and quiet. The location was very convenient and walkable to downtown's many excellent restaurants and the Shakespeare Festival. Would definitely stay there again.

Reviewed on Sep 5, 2026

Hanna's House by WanderLodges

Hanna's House by WanderLodges

4 out of 5
Price was $830, price is now $647 per person
$647
per person
Nov 5 - Nov 10
found 2 hours 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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $642, price is now $515 per person
$515
per person
Nov 5 - Nov 10
found 2 hours 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.

Savage Upon Siskiyou

Savage Upon Siskiyou

3 out of 5
Save 100% on your flight
Price was $1,320, price is now $1,066 per person
$1,066
per person
Nov 5 - Nov 10
found 2 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Stay at this vacation home in Ashland. Enjoy free WiFi, free parking, and a garden. Popular attractions Oregon Shakespeare Festival and Ashland Library are located nearby.
Had an amazing stay, thank you!

Reviewed on Aug 5, 2026

Wine Country Inn

Wine Country Inn

3 out of 5
Price was $546, price is now $455 per person
$455
per person
Nov 5 - Nov 10
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.

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Price was $699, price is now $583 per person
$583
per person
Nov 5 - Nov 10
found 2 hours 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.

Trail 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 $579, price is now $533 per person
$533
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $660, price is now $556 per person
$556
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
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
Historic Downtown District
Price was $678, price is now $598 per person
$598
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
Stratford Inn

Stratford Inn

2.5 out of 5
Siskiyou-Hargadine Historic District
Price was $601, price is now $548 per person
$548
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip non-stop 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.
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $642, price is now $515 per person
$515
per person
Nov 5 - Nov 10
found 2 hours 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 $756, price is now $560 per person
$560
per person
Nov 5 - Nov 10
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 $811, price is now $618 per person
$618
per person
Nov 5 - Nov 10
found 2 hours 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 $830, price is now $647 per person
$647
per person
Nov 5 - Nov 10
found 2 hours 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 days ago
$219
Roundtrip
found 3 days 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 days ago
United
Fri, Nov 6 - Wed, Nov 11
PDX
Portland Intl.
MFR
Rogue Valley Intl.
$266 Roundtrip, found 19 hours ago
$266
Roundtrip
found 19 hours ago
Select United flight, departing Fri, Nov 6 from Portland Intl. to Rogue Valley Intl., returning Wed, Nov 11, priced at $266 found 19 hours ago
Bargain Flight
Sat, Oct 3 - Tue, Oct 6
SFO
San Francisco Intl.
MFR
Rogue Valley Intl.
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day 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 1 day ago
Bargain Flight
Thu, Dec 17 - Fri, Dec 25
DEN
Denver Intl.
MFR
Rogue Valley Intl.
$315 Roundtrip, found 1 day ago
$315
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Thu, Dec 17 from Denver Intl. to Rogue Valley Intl., returning Fri, Dec 25, priced at $315 found 1 day ago