Jacksonville Cottages - Nightly & Monthly Rentals in Jacksonville, Oregon

Live Music at Dancin Vineyards
2026-05-29 17:00 - 19:00 (America/New_York) | DANCIN Vineyards, 4477 South Stage Road, Medford, OR, 97501, United States
Live music by David Pinsky & Phil Newton

Friday Nights Live Music at Hummingbird Estate
2026-05-29 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
2026-05-29 19:00 - 22:00, 2026-05-30 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

Jacksonville “Walk Through History” Tour
2026-05-30 10:00 - 11:00 (America/Los_Angeles) | Jacksonville City Hall, 206 N 5th St, Jacksonville, OR, United States
Walk through Jacksonville History!
JACKSONVILLE, OR—Jacksonville’s “Walk through History” tours are back! At 10 a.m. every Saturday from May 30th through September 5th, Historic Jacksonville, Inc. will be offering one-hour guided walks through Jacksonville’s National Historic Landmark District, the first on the West Coast! Participants will take a stroll through history, visiting government and commercial buildings, fraternal lodges, and homes that capture the stories of the people who transformed a gold rush town into Southern Oregon’s 19th Century social, governmental, and commercial hub. They’ll learn how gambling money built a church; how the Civil War ended a successful mercantile partnership; how a saloon housed the county’s first museum; how fire reshaped the town; and how a railroad both destroyed the town and preserved it.
Walking tours leave from Jacksonville’s New City Hall (the historic “Courthouse Square”) at 206 North 5th Street between West C and D streets and cover about one mile with multiple stops. Tours are FREE but donations are encouraged! All monies go towards the preservation and maintenance of Jacksonville’s historic buildings.
For individuals who prefer not to “stretch their legs,” Historic Jacksonville’s website (https://www.historicjacksonville.org) offers numerous ways to explore Jacksonville virtually. These include multiple blogs about the town and its settlers along with three video tours that introduce viewers to Jacksonville’s Historic Landmark District, its Historic Homes, and its Pioneer Cemetery.
Historic Jacksonville, Inc. invites you to forget the “names, dates, places, and battles” version of history you may have been taught in school. HJI’s live and virtual tours are about “real history”—people and their stories. They are about life!
Additional information on “Walk through History” and other Historic Jacksonville, Inc. tours is available at 541-245-3650; info@historicjacksonville.org; and www.historicjacksonville.org.

Guided History Walking Tour – about 1 mile
2026-05-30 10:00 - 11:00 (America/New_York) | Jacksonville City Hall, 206 N 5th St, Jacksonville, OR, United States
Donation

Beekman Bank Behind the Counter Tours
2026-05-30 11:00 - 15:00, 2026-05-31 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/

Experience how banking was conducted in the late 1800’s
2026-05-30 11:00 - 15:00, 2026-05-31 11:00 - 15:00 (America/New_York) | Beekman Bank, corner of California and North 3rd streets, Jacksonville, OR, 97530, United States

Live Music at Daisy Creek Vineyards
2026-05-30 13:00 - 15:00 (America/New_York) | Daisy Creek Vineyard, 675 Shafer Lane, Jacksonville, OR, 97530, United States
Music Bingo

Paws to Read: Read with a dog
2026-05-30 14:00 - 15:00 (America/New_York) | Jacksonville Library, 340 W. C Street, Jacksonville, OR, 97530, United States

Artist & Gardener 10th-Anniversary Celebration!
2026-05-30 14:00 - 17:00 (America/Los_Angeles) | Artist and Gardener, 130 S 3rd St, Jacksonville, OR, United States
Come help us celebrate 10 years of Artist & Gardener at our little corner of town on May 30, 2026. We have much to be thankful for and want to share the joy we feel with those that helped make it possible. Food and drink will be provided in the garden. 2pm–?130 South Third Street, Jacksonville 541-702-2555

Live Music at Rellik Winery
2026-05-30 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 Dos Mariposas Vineyards
2026-05-30 16:00 - 18:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States
Live music by Hopstone

Live Music at Rellik Winery
2026-05-30 16:00 - 18:00 (America/New_York) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
Live music by Sterling Vintage Jazz
Please check out our calendar for list of performances: Rellik Winery Calendar

Live Music at Remotion Wine
2026-05-30 17:00 - 19:00 (America/New_York) | Remotion Wine, 105 W. Main Street, Jacksonville, OR, 97530, United States
Live music by Keenan Pruett

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

Live Music at The Wine Lounge at The Jacksonville Inn
2026-05-30 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 The Bella Union Restaurant & Saloon
2026-05-30 19:00 - 22:00 (America/New_York) | Bella Union Restaurant & Saloon, 170 W. California St, Jacksonville, OR, 97530, United States
Live music by Jared Gutridge
Check our website for list of entertainment: Live Music at the Bella

Brunch at Rellik Winery
2026-05-31 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
2026-05-31 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

Open Mic Afternoon at Dos Mariposas Vineyards
2026-05-31 14:00 - 17:00 (America/New_York) | Dos Mariposas Vineyards and Lavendar Farm, 3976 Bellinger Lane, Medford, OR, 97501, United States

Live Music at Rellik Winery
2026-05-31 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

Jacksonville-Applegate Rotary Fork & Cork at Rellik Winery
2026-05-31 16:30 - 19:30 (America/Los_Angeles) | Rellik Winery, 970 Old Stage Rd, Central Point, OR, 97502
MARK YOUR CALENDARS! The Jacksonville-Applegate Rotary Club is bringing back one of the Rogue Valley’s most beloved fundraising evenings, Fork & Cork, on Sunday, May 31, from 4:30-7:30pm at Rellik Winery, 970 Old Stage Road, in Central Point.
Fork & Cork guests can expect live music, a delicious tri-tip dinner, and a lively auction, all set against the beautiful backdrop of one of the region’s favorite wineries. Tickets are $50 per person or $250 for a table of six, making it a perfect outing for friends, family, or colleagues who want an enjoyable evening with real purpose behind it.
And that purpose runs deep. Every dollar raised at Fork & Cork goes directly toward local education initiatives and scholarships, clean water projects in Mexico and Africa, and support for homeless children’s education in Guatemala. The Jacksonville-Applegate Rotary Club has long believed that doing good locally and thinking globally are not mutually exclusive, and Fork & Cork is a shining example of that philosophy in action.
Come for the Tri-tip. Stay for the music. Leave knowing you made a difference.
For more information and to purchase tickets: https://jacksonvilleapplegaterotary.org/jacksonville-fork-cork/
