Name: Come relax, work & enjoy country air. Beautiful winter has arrived!
Rating: 9.2

Top Beach vacation packages in Southern Oregon

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

Paschal Winery

$337

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (15 reviews)

It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.

Reviewed on May 3, 2025

Hummingbird Estate Wine & Suites

$425

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (145 reviews)

Charming vintage winery with great history and lovely rooms. The Syrah suite was clean and comfortable. The sunrise in the morning was spectacular. The tasting room is directly below the suite and can be loud but closes around 7 during the week. I don’t think I would stay here during an event unless I was participating in the event. So check the calendar first if noise is an issue for you. The grounds are wonderful and there are many spots to sit and enjoy. At night the terrace is lovely with the fires going. We played a bit of pickleball as well. Highly recommend with the caveat of checking for events first if noise is an issue for you.

Reviewed on Feb 28, 2026

Compass by Margaritaville in Medford

$438

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (1,000 reviews)

Room was new, clean, and comfy. Complementary breakfast was really good and all the staff were amazing

Reviewed on Mar 1, 2026

McCall House Boutique Inn

Historic Downtown District

$497

per person

Apr 24 - Apr 26

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.2/10 Wonderful! (574 reviews)

Room clean, great breakfast

Reviewed on Mar 1, 2026

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4 Night Beach vacations in Southern Oregon

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

Paschal Winery

$337

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (15 reviews)

It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.

Reviewed on May 3, 2025

Hummingbird Estate Wine & Suites

$425

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.6/10 Exceptional! (145 reviews)

Charming vintage winery with great history and lovely rooms. The Syrah suite was clean and comfortable. The sunrise in the morning was spectacular. The tasting room is directly below the suite and can be loud but closes around 7 during the week. I don’t think I would stay here during an event unless I was participating in the event. So check the calendar first if noise is an issue for you. The grounds are wonderful and there are many spots to sit and enjoy. At night the terrace is lovely with the fires going. We played a bit of pickleball as well. Highly recommend with the caveat of checking for events first if noise is an issue for you.

Reviewed on Feb 28, 2026

Wine Country Inn

$354

per person

Apr 24 - Apr 28

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.4/10 Exceptional! (1,002 reviews)

Fantastic rooms and areas.

Reviewed on Feb 23, 2026

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How do I book the best Southern Oregon beach vacation packages?

Life’s a beach when you dive into our brilliant Southern Oregon beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Southern Oregon?

A rental steps from the shore creates an amazingly affordable Southern Oregon beach vacation. Seaside sojourns during low season start from $337. Prices and availability are subject to change. Additional terms may apply.

When should I book a Southern Oregon beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Southern Oregon?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Southern Oregon beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Southern Oregon vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Southern Oregon beach vacation deals?

Sort your search results by deals to delight in amazing Southern Oregon beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Southern Oregon beach trip with free cancellation and/or flexible dates?

Just like the Southern Oregon tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Southern Oregon beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Southern Oregon. (OK, maybe not that last part.)

Top Beach Southern Oregon Hotels

Historic Dunn Ranch Ashland Oregon. Sleeps 12 to 14 Great for large groups.

Ashland OR

2 hours drive from Crater Lake National Park

Book a stay at this family-friendly farm stay in Ashland. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Weisinger Family Winery ...

9.8/10 Exceptional! (15 reviews)

The family enjoyed the hot tub and the game room and weather behaved for us. The only suggestion we have is to have a dimmer switch in the dining room. The light fixture was too bright.

Reviewed on Feb 20, 2026

HISTORIC RUSHING WATER LODGE on the rogue river was built in 1910

Eagle Point OR

1 hour drive from Crater Lake National Park

Stay at this lodge in Eagle Point. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Eagle Point Library and Agate River Vineyard are located ...

10/10 Exceptional! (34 reviews)

Such a comfy spot on the river and perfect for the whole family. This is our second time staying there and it did not disappoint!!

Reviewed on Dec 27, 2025

Come relax, work & enjoy country air. Beautiful winter has arrived!

Ashland OR

2 hours drive from Crater Lake National Park

Book a stay at this family-friendly farm stay in Ashland. Enjoy free WiFi, a water park, and a garden. Popular attractions Weisinger Family Winery and Emigrant ...

9.2/10 Wonderful! (69 reviews)

We come back every year for a ski weekend. Perfect family place

Reviewed on Jan 24, 2026

See all 1,416 properties in Southern Oregon

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.