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Prospect Vacation Packages

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Prospect 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 $621, price is now $518 per person
$518
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop 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.

Winchester Inn

Winchester Inn

3.5 out of 5
Price was $714, price is now $599 per person
$599
per person
Dec 18 - Dec 21
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.
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

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $733, price is now $632 per person
$632
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Salt Lake City (SLC) 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

Savage Upon Siskiyou

Savage Upon Siskiyou

3 out of 5
Price was $1,109, price is now $956 per person
$956
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop 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 Ashland Library and Oregon Cabaret Theatre are located nearby.
Had an amazing stay, thank you!

Reviewed on Aug 5, 2026

Hanna's House by WanderLodges

Hanna's House by WanderLodges

4 out of 5
Price was $782, price is now $682 per person
$682
per person
Nov 7 - Nov 10
found 14 hours ago
Roundtrip flight included
Salt Lake City (SLC) 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

Rosewood Collective- House & Studio

Rosewood Collective- House & Studio

3 out of 5
Price was $1,025, price is now $902 per person
$902
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop 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.

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Price was $684, price is now $608 per person
$608
per person
Dec 18 - Dec 21
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.
We enjoyed our stay. The room was clean & the bed was comfortable. The breakfasts were very good; with a different menu every morning. From the house to the OSF theaters is an easy walk.

Reviewed on Sep 26, 2026

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Price was $597, price is now $532 per person
$532
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip non-stop 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 Ashland Library and Oregon Cabaret Theatre are located nearby.

Prospect Vacation Packages 5-7 Night Stays

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

Stratford Inn

2.5 out of 5
Siskiyou-Hargadine Historic District
Price was $507, price is now $456 per person
$456
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Lithia Springs Resort

Lithia Springs Resort

3 out of 5
Price was $534, price is now $481 per person
$481
per person
Nov 5 - Nov 10
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
The Lodge at Riverside

The Lodge at Riverside

3 out of 5
Price was $641, price is now $592 per person
$592
per person
Nov 5 - Nov 10
found 3 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
Price was $594, price is now $550 per person
$550
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)