Jacksonville Cottages - Nightly & Monthly Rentals in Jacksonville, Oregon

Live Music at Dos Mariposas Vineyards
2026-05-22 17:30 - 19:30 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by Hopfinger Wishes

Friday Nights Live Music at Hummingbird Estate
2026-05-22 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
2026-05-22 19:00 - 22:00, 2026-05-23 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 The Bella Union Restaurant & Saloon
2026-05-22 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 by Aaron Reed

Rogue Valley Symphony Masterworks 6 at SOU Recital Hall
2026-05-22 19:30 - 20:30 (America/Los_Angeles) | SOU Recital Hall, Ashland, OR, United States
Rogue Valley Symphony Masterworks 6:

Friday, May 22, 7:30pm, SOU Recital Hall, Ashland
Saturday, May 23, 3pm, Craterian Theater, Medford
Sunday, May 24, 3pm, Grants Pass Performing Arts Center, Grants Pass

www.RVSymphony.org or call 541-708-6400

Beekman Bank Behind the Counter Tours
2026-05-23 11:00 - 15:00, 2026-05-24 11:00 - 15:00 (America/Los_Angeles) | Beekman Bank 1863, 400 W California St, Jacksonville, OR, United States
Step behind the counter of the historic Beekman Bank. Every weekend May 23 – September 6, 2026, 11am-3pm Oldest bank in the Pacific Northwest!Over $40 million in gold crossed its counters in the 1800s.(Equal to $1.5 billion+ today!) FREE – Donations welcomed! 110 W. California Street, Jacksonville, Oregon 97530 https://www.historicjacksonville.org/behind-the-counter-tours/

The Atrium Foundation 5-Year Anniversary Celebration at Dos Mariposas
2026-05-23 13:00 - 15:00 (America/Los_Angeles) | Dos Mariposas Vineyards & Lavender, 3976 Bellinger Ln, Medford, OR, United States
Saturday, May 23, 1-3pm: The Atrium Foundation 5-Year Anniversary Celebration.
Dos Mariposas Vineyards & Lavender Farm. Not a formal event – just come by to meet the founder and learn more! https://atriumfoundation.org

Paws to Read: Read with a Dog
2026-05-23 14:00 - 15:00 (America/New_York) | Jacksonville Library, 340 W. C Street, Jacksonville, OR, 97530, United States

Rogue Valley Symphony Masterworks 6 at Craterian Theater
2026-05-23 15:00 - 16:30 (America/Los_Angeles) | Craterian Theater at The Collier Center for the Performing Arts, 23 S Central Ave, Medford, OR, United States

Live Music at Rellik Winery
2026-05-23 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 Daisy Creek Vineyards
2026-05-23 16:00 - 18:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Live music by Holly Gleason Special

Live Music at Dos Mariposas Vineyards
2026-05-23 16:00 - 18:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by Aaron Reed

Live Music at Rellik Winery
2026-05-23 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 by J Brothers

Live Music at Remotion Wine
2026-05-23 17:00 - 19:00 (America/New_York) | Remotion Wine, 105 W. Main Street, Jacksonville, OR, 97530, United States
Live music by Chrisman and Smith

Live Music at South Stage
2026-05-23 17:30 - 19:30 (America/New_York) | South Stage Cellars, 125 S. 3rd. St, Jacksonville, OR, 97530, United States
Live music by Rogue Suspects
$20 Reservation

Live Music at The Wine Lounge at The Jacksonville Inn
2026-05-23 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

Brunch at Rellik Winery
2026-05-24 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
2026-05-24 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 Vineyards
2026-05-24 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 by Erica Rochel Duo

Rogue Valley Symphony Masterworks 6 at Grants Pass Performing Arts Center
2026-05-24 15:00 - 16:30 (America/Los_Angeles) | Grants Pass Performing Arts Center, 313 NE Olive St, Grants Pass, OR, United States

Live Music at Rellik Winery
2026-05-24 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Please check out our website for list of performances: Rellik’s Calendar

Live Music at Rellik Winery
2026-05-24 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Please check out our website for list of performances: Rellik’s Calendar
Live music by Alois Trio

MEMORIAL DAY
2026-05-25 08:00 - 17:00 (America/New_York) | OR
MEMORIAL DAY: We honor & mourn the military personnel who died while serving the United States of America

Live Music at Dancin Vineyards
2026-05-25 17:00 - 19:00 (America/New_York) | DANCIN Vineyards, 4477 South Stage Road, Medford, OR, 97501, United States
Live music by Jeff Kloetzel

Tuesday Tunes at The Wine Lounge at The Jacksonville Inn
2026-05-26 18:00 - 20:00 (America/New_York) | The Wine Lounge at the Jacksonville Inn, 175 E. California Street, Jacksonville, 97530, United States
Catch live music at The Wine Lounge at Jacksonville Inn every Tuesday night.

Catch live music at The Wine Lounge at Jacksonville Inn every Tuesday night. The Lounge offers a wide selection of local wines to try by the glass or bottle (No Corkage fee!), and a nice complimentary menu to nosh on. This is a great local hang.

Preschool Music & Movement – Weekly on Wednesdays 11am-Noon
2026-05-27 11:00 - 12:00 (Asia/Dubai) | Jacksonville Community Center, 160 E. Main St, Jacksonville, OR, 97530, United States
At Jacksonville Community Center every Wednesday 11am – Noon, discover the joy of music in this engaging class designed for children 2-5 and their caregivers. This class combines singing, rhythm, movement and sign language. Get ready to sing beloved songs from around the world, and make music together in this weekly class! Sponsored by Jackson Care Connect. ADULTS ARE FREE attending with child(ren). $5 per child. Walk-ins ALWAYS welcome.
Instructor Bios: Laurie Finear has been a music teacher in the Rogue Valley for over 15 years as a certified Music Together teacher. She now creates and teaches her own music classes for children and their caregivers in Ashland and Jacksonville. She is passionate about sharing the joy of music with children and families.

Pinot & Pages at Hummingbird Estate
2026-05-27 17:00 - 19:00 (America/New_York) | Hummingbird Estate, OR, 97502, United States
Attention all writers! Join us every Wednesday from 5-7pm. Grab a glass of wine & let the words flow!
Bring your journal or laptop and join a table of fellow writers for focused, quiet writing time. It’s not a workshop or a class-just a chill space to show up, sip and let the words flow. RSVP not required.
