Jacksonville Cottages - Nightly & Monthly Rentals in Jacksonville, Oregon

Live Music at Daisy Creek Vineyards
2026-05-15 17:00 - 19:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music every Friday! Check our calendar for performances: Daisy Creek Calendar

Live music at Rellik Winery
2026-05-15 17:00 - 19:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Live music by Cathy Bolton

Live music at Daisy Creek Vineyard
2026-05-15 17:00 - 19:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music by Bryan Oliver

Live Music at Dancin Vineyards
2026-05-15 17:00 - 19:00 (America/New_York) | DANCIN Vineyards, 4477 South Stage Road, Medford, OR, 97501, United States
Live music by The Giantess

Live Music at Dos Mariposas
2026-05-15 17:30 - 19:30 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by Allison Scull & Victor Martin

Friday Nights Live Music at Hummingbird Estate
2026-05-15 18:30 - 20:30 (Asia/Dubai) | Hummingbird Estate, OR, 97502, United States
Join us for an evening of music from 6:30-8:30pm on our side lawn, now featuring a brand new stage platform! Enjoy delicious eats from Pizza Mia and relax in the Hummingbird atmosphere. Bring a lawn chair for comfortable seating. Food truck starts at 6:00pm. Come early, grab a bite, and settle in for a great night.

Live Music at The Bella Union Restaurant & Saloon
2026-05-15 19:00 - 22:00, 2026-05-16 19:00 - 22:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Join us for live music, great food and spirits every Friday & Saturday
Check our website for list of entertainment: Live Music at the Bella

Live music at Bella Union Restaurant and Saloon
2026-05-15 19:00 - 22:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Live music by Sonido Alegre

Southern Oregon True Crime Summit
2026-05-16 | Bigham Knoll Campus, 399 Bigham Dr, Central Point, OR, United States
ON MAY 15 & 16, the public is invited to attend the Southern Oregon True Crime Summit at the Bigham Knoll Campus, founded and produced by local Melynda Cordes. The event features professionals and experienced voices in forensic science, investigative journalism, law enforcement, victim advocacy, and ethical true crime media. This 2-day informational summit will focus on forensic investigation, missing persons cases, cold cases, victim advocacy, and responsible storytelling. Cordes notes, “The event includes expert-led panels, keynote talks, and immersive experiences, including a podcast listening party and a True Crime Lecture, designed for the general public, professionals, students, and true crime audience, not just academics.”
The main event features a book signing by Lindsay Wade in the ballroom at Bigham Knoll, (525 Bigham Knoll Drive). A Macabre Podcast listening party and True Crime Trivia, Malice in the Mist, will be hosted at Remotion Wine Tasting Room, 105 W. Main Street in Jacksonville.
The summit was created to encourage thoughtful discussion, public awareness, and community connection around real cases and real people, while offering approachable insight into how investigations, advocacy, and the media intersect in the real world. Cordes expects guests to attend from Washington, Oregon, Idaho, California, Nevada, and the broader Pacific Northwest. The event is structured to be accessible and engaging for a wide audience, including true crime listeners, community members, students, and professionals alike.
A portion of the proceeds will be donated to local and regional organizations, including Jackson County SART, Crescent City PD Search and Rescue K9 Unit/Cadaver Dogs and the Oregon Cold Case Collective. Please find all the event details, speaker announcements, and registration information at https://southernoregontruecrime.com/.

Cemetery Marker Cleaning Workshop
2026-05-16 09:00 - 12:00 (America/Los_Angeles) | Jacksonville Cemetery, Jacksonville, OR, United States
Marker Cleaning Workshop, Saturday, May 16, 9am-noon—Come learn the latest techniques to safely clean and preserve the grave markers in our cemetery. This is a hands-on workshop, so dress accordingly. Bring a stool to sit on, plus sunscreen and a hat. Please check our website at friendsjvillecemetery.org for future events and programs.

Marker Cleaning Workshop at Jacksonville Cemetery
2026-05-16 09:00 - 12:00 (America/New_York) | Jacksonville Cemetery, Jacksonville, OR, United States
Marker Cleaning Workshop

Uncorked Barrel Wine Tour in Applegate Valley Wine Country
2026-05-16 11:00 - 16:00 (America/New_York) | Applegate Valley Wine, PO Box 1215, Jacksonville, OR, 97530, United States
Come celebrate growing season with a self-guided tour of the Applegate Valley Wine Country. Fall is the perfect time to visit our 16 tasting rooms. The winegrapes have been picked, pressed, and barreled, and the winemakers have time to chat.
Pick your starting location, and let yourself be lured from one winery to the next. Each will offer an appetizer and wine for tasting. You’ll even get to meet some of the latest releases! Uncorked is a great opportunity to stock up on wine for upcoming gifts, or parties.
Tickets are $59 and include a commemorative Wine Trail wine glass.
Bonus: Designated drivers tickets are FREE and they may sample the food.

Applegate Valley Wineries Uncorked Wine Barrel Tour
2026-05-16 11:00 - 16:00 (America/Los_Angeles) | Applegate Valley, Oregon
Saturday, May 16, 11am-4pm: Applegate Valley Wineries Uncorked Wine Barrel Tour.

Special Wine Tastings & Food Pairings at 16 Applegate Wineries.

Tickets $59 each – includes a wine glass.

Tickets and more info at applegatevalley.wine

Beekman House Tours: Daily Life Then and Now
2026-05-16 12:00 - 15:00 (America/Los_Angeles) | Beekman House, 452 E California St, Jacksonville, OR, United States
An old song notes “What a difference a day makes!” Well, think about what a difference 125 years can make!
Daily Life Then and Now
1870s C.C. Beekman House, is located at 470 E. California Street in Jacksonville, Oregon.
Join Historic Jacksonville, Inc. on Saturday, May 16, 2026, for “Daily Life Then and Now” tours—a 1900 vs. 2026 comparison of a family’s daily lifestyle. Visit the difference in communication, fashion, etiquette, entertainment, chores, household “amenities,” and much more – things we take for granted like electricity, running water, and…bathrooms!

45 minute tours every half hour between noon and 3pm.
Tour admission is $8 (cash or check at the door).
All proceeds go towards maintenance of Jacksonville’s historic buildings and the programs and events that bring them to life and make them relevant for people today.

https://historicjacksonville.org/then-and-now/

Tours of Daily Life Then & Now 1900 vs 2026 at Beekman House
2026-05-16 12:00 - 15:00 (America/New_York) | Beekman House, 452 E California St, Jacksonville, OR, United States
Tours of Daily Life Then & Now 1900 vs 2026
$8 cash or check at door

Paws to Read: Read with a dog at Jacksonville Library
2026-05-16 14:00 - 15:00 (America/New_York) | Jacksonville Library, 340 W. C Street, Jacksonville, OR, 97530, United States
Paws to Read: Read with a dog

Third Saturday: Block Printing with Belinda Moffit
2026-05-16 14:00 - 17:00 (America/New_York) | Art Presence Art Center, 206 N 5th St, Jacksonville, OR, United States
Spend a creative afternoon with Belinda Moffit and learn the timeless craft of block printing. Whether you’re a total beginner or a seasoned pro, you’ll be guided through every step – from designing and carving your block to pulling your very first print. We provide all the supplies; you just bring the creativity! Registration Required,Limit 15, $40

Live Music at Rellik Winery
2026-05-16 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Please check out our calendar for list of performances: Rellik Winery Calendar

Live Music at Rellik Winery
2026-05-16 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502

Live Music at Dos Mariposas Vineyards
2026-05-16 16:00 - 18:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by 12 Bars Deep

Live Music at Dancin Vineyards
2026-05-16 17:00 - 19:00 (America/New_York) | DANCIN Vineyards, 4477 South Stage Road, Medford, OR, 97501, United States
Live music by Lisa & Dean

Live Music at South Stage
2026-05-16 17:30 - 19:30 (America/New_York) | South Stage Cellars, 125 S. 3rd. St, Jacksonville, OR, 97530, United States
Live music by Left
$20 Reservation

Live Music at The Wine Lounge at The Jacksonville Inn
2026-05-16 18:00 - 20:00 (America/New_York) | The Wine Lounge at the Jacksonville Inn, 175 E. California Street, Jacksonville, 97530, United States
Live music every Saturday Night! Check the website for details: The Wine Lounge Events

Live Music at Bella Union Restaurant & Saloon
2026-05-16 19:00 - 22:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Live music by Shabby Guys

Dos Mariposas
2026-05-17 | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States

Live Music at Dos Mariposas Vineyards
2026-05-17 08:00 - 17:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States

Brunch at Rellik Winery
2026-05-17 10:30 - 13:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Come join us for our weekly Sunday brunch at Rellik Winery.

Live Music at Daisy Creek Vineyards
2026-05-17 14:00 - 16:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music every Sunday afternoon! Check our website for performances: Daisy Creek Calendar

Live Music at Daisy Creek Vineyard
2026-05-17 14:00 - 16:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music by Jen Ambrose & The Mystic Trio
