Search Deals onO'Brien Vacation Packages
O'Brien Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
A Cowslip's Belle Inn
Price was $663, price is now $599 per person
$599
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Medford (MFR)
Book a stay at this business-friendly apartment in Ashland. Enjoy free WiFi, free parking, and an in-room coffeemaker. Popular attractions Oregon Shakespeare Festival and Allen Elizabethan Theatre are located nearby.
The Cowslips Belle Inn is amazing! Just a few short blocks from the Oregon Shakespeare Festival, many fine eateries and downtown Ashland. The grounds are superb with well tended landscaping, cozy seating areas and a wonderful koi pond. An off street parking area just for guests is excellent. The hosts were very gracious and friendly, personally greeting us and showing us our suite. The suite is beautifully decorated and very cozy with all the amenities that one might need. The notebook with restaurant recommendations, outlines of all the possibilities of things to do and entertainments in the area plus bios on all 3 hosts is a real plus. And the price is excellent for this wonder! Would highly recommend this Inn for a short or long stay in Southern Oregon.
Reviewed on Aug 7, 2026
Winchester Inn
Price was $1,624, price is now $1,269 per person
$1,269
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Denver (DEN) 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
Riverfront Lodging
Price was $730, price is now $621 per person
$621
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
Stay at this motel in Shady Cove. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Upper Rogue Regional County Park and Shady Cove Library are located nearby.
Good air conditioning it was over 100 degrees the day I stayed. Staff very nice. There is a nice river side deck and cooler by the river. Great bed and shower. I would definitely stay there again. Very quiet.
Reviewed on Aug 15, 2026
McCall House Boutique Inn
Price was $1,183, price is now $1,025 per person
$1,025
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Edgewater Inn Shady Cove
Price was $777, price is now $684 per person
$684
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
Stay at this hotel in Shady Cove. Enjoy free parking, laundry facilities, and satellite TV channels. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Upper Rogue Regional County Park and Shady Cove Library are located nearby.
The motel was serene and peaceful. Staffs were helpful. Nice place to stay.
Reviewed on Aug 11, 2026
Callahan's Mountain Lodge
Price was $1,053, price is now $928 per person
$928
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to Medford (MFR)
Book a stay at this family-friendly lodge in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tashi Choling Buddhist Center and Bull Gap Lower Trailhead are located nearby.
The Peerless Hotel by WanderLodges
Price was $732, price is now $657 per person
$657
per person
Sep 25 - Sep 27
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 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
Wine Country Inn
Price was $809, price is now $727 per person
$727
per person
Sep 20 - Sep 24
found 19 hours ago
Roundtrip 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.
The bed was lumpy.
Vinyl flooring.
Very small TV that was not visible from the bed.
Limited breakfast options.
Reviewed on Aug 17, 2026
O'Brien Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
O'Brien Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Sep 23 - Tue, Sep 29
LAX
Los Angeles Intl.
MFR
Rogue Valley Intl.
$226 Roundtrip, found 4 days ago
$226
Roundtrip
found 4 days ago
Fri, Nov 6 - Wed, Nov 11
PDX
Portland Intl.
MFR
Rogue Valley Intl.
$235 Roundtrip, found 4 hours ago
$235
Roundtrip
found 4 hours ago
Sat, Sep 12 - Sat, Sep 19
LAS
Harry Reid Intl.
MFR
Rogue Valley Intl.
$313 Roundtrip, found 4 days ago
$313
Roundtrip
found 4 days ago
Tue, Sep 22 - Tue, Sep 29
CLD
McClellan-Palomar
MFR
Rogue Valley Intl.
$323 Roundtrip, found 5 days ago
$323
Roundtrip
found 5 days ago
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