Vacation Rentals in Jacksonville, Oregon

26 Properties Available

Experience charming Jacksonville, OR in this 8-bedroom Historic Inn. Enjoy a wine country getaway with 8 private bedrooms. Walk to dining, shopping, and the famed Britt Festival grounds. Hotel
Experience charming Jacksonville, OR in this 8-bedroom Historic Inn. Enjoy a wine country getaway with 8 private bedrooms. Walk to dining, shopping, and the famed Britt Festival grounds.
$1967 / night
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Private vineyard sanctuary for 8. Savor coffee at sunrise in the backyard oasis, soak in the hot tub under starry skies, and enjoy this elegant spacious retreat with mountain views, minutes from Historic Jacksonville and Applegate’s wine country. Private vacation home
Private vineyard sanctuary for 8. Savor coffee at sunrise in the backyard oasis, soak in the hot tub under starry skies, and enjoy this elegant spacious retreat with mountain views, minutes from Historic Jacksonville and Applegate’s wine country.
$604 / night
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Park like setting on the Applegate River great for wine tasting & family reunion Private vacation home
Park like setting on the Applegate River great for wine tasting & family reunion
$476 / night
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Jacksonville Suites 160 - A Pristine Cheery Mid-Century Gem Private vacation home
Jacksonville Suites 160 - A Pristine Cheery Mid-Century Gem
$341 / night
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Applegate Valley Peaceful Cottage Cottage
Applegate Valley Peaceful Cottage
$300 / night
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The Orth House Inn by Remotion Inn
The Orth House Inn by Remotion
$278 / night
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Boutique 1 BR King Suite in historic downtown Jacksonville. Walk to the Britt Festival! Enjoy a king bed, modern rain shower, and charming Inn details. Ideal for a romantic or weekend getaway. Hotel
Boutique 1 BR King Suite in historic downtown Jacksonville. Walk to the Britt Festival! Enjoy a king bed, modern rain shower, and charming Inn details. Ideal for a romantic or weekend getaway.
$271 / night
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Boutique 1 BR King Guest Room in historic Jacksonville, OR. Features a plush King bed, Nespresso machine, and charming Inn details. Perfect for a comfortable, walkable downtown escape. Hotel
Boutique 1 BR King Guest Room in historic Jacksonville, OR. Features a plush King bed, Nespresso machine, and charming Inn details. Perfect for a comfortable, walkable downtown escape.
$264 / night
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Boutique 1 BR King Suite in historic Jacksonville. Walk to Britt Festival and wine tasting! Features a luxurious tub, comfortable king bed, and charming Inn details. Ideal for couples Hotel
Boutique 1 BR King Suite in historic Jacksonville. Walk to Britt Festival and wine tasting! Features a luxurious tub, comfortable king bed, and charming Inn details. Ideal for couples
$262 / night
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Jacksonville Inn Room #5: Luxurious 1 BR King Guest Room. Walkable to the Britt Festival, downtown shops, and wine tasting rooms. Experience historic charm with modern comfort! Hotel
Jacksonville Inn Room #5: Luxurious 1 BR King Guest Room. Walkable to the Britt Festival, downtown shops, and wine tasting rooms. Experience historic charm with modern comfort!
$261 / night
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Jacksonville Inn Room #8: King Suite. Prime downtown location for festivals and dining. Comfortable king bed, Nespresso coffee, and historic boutique elegance Hotel
Jacksonville Inn Room #8: King Suite. Prime downtown location for festivals and dining. Comfortable king bed, Nespresso coffee, and historic boutique elegance
$261 / night
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Charming 1 BR Queen Guest Room at the Historic Jacksonville Inn. Walk to downtown shops, dining, and the Britt Festival grounds. Perfect for a quick stopover or a romantic Oregon wine country visit. Hotel
Charming 1 BR Queen Guest Room at the Historic Jacksonville Inn. Walk to downtown shops, dining, and the Britt Festival grounds. Perfect for a quick stopover or a romantic Oregon wine country visit.
$256 / night
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Experience charming Jacksonville! This 1 BR Queen Guest Room at the Historic Inn is perfect for a wine country retreat. Walkable location, antique charm, and a comfortable Queen bed. Hotel
Experience charming Jacksonville! This 1 BR Queen Guest Room at the Historic Inn is perfect for a wine country retreat. Walkable location, antique charm, and a comfortable Queen bed.
$256 / night
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Experience historic Jacksonville! This 1 BR Queen Guest Room offers boutique charm in the heart of wine country. Walk to the Britt Festival, Nespresso machine included. Ideal for a downtown escape for two. Hotel
Experience historic Jacksonville! This 1 BR Queen Guest Room offers boutique charm in the heart of wine country. Walk to the Britt Festival, Nespresso machine included. Ideal for a downtown escape for two.
$256 / night
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Cowgirl Craftsman - Private King Suite Upstairs - Historic Downtown J'ville Private vacation home
Cowgirl Craftsman - Private King Suite Upstairs - Historic Downtown J'ville
$219 / night
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The Lindsay Lodge & Restaurant Hotel
The Lindsay Lodge & Restaurant
$215 / night
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Cottage 9 – Downtown Jacksonville Retreat Steps from Shops & Britt Gardens Private vacation home
Cottage 9 – Downtown Jacksonville Retreat Steps from Shops & Britt Gardens
$210 / night
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Cottage : 1925 Private vacation home
Cottage : 1925
$186 / night
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Studio 5 at Kubli Haus Private vacation home
Studio 5 at Kubli Haus
$179 / night
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Lovely Private 1 Bedroom/Bathroom in Historic Log Home. Host occupied. Bed & breakfast
Lovely Private 1 Bedroom/Bathroom in Historic Log Home. Host occupied.
$142 / night
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Charleen's Cottage~Couple Perfect!Great Location! A Gem! Guest house
Charleen's Cottage~Couple Perfect!Great Location! A Gem!
$135 / night
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Cozy private family ranch cottage! Vineyards, Britt Festival and Applegate Lake! Cottage
Cozy private family ranch cottage! Vineyards, Britt Festival and Applegate Lake!
$113 / night
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Valhalla Cabin in Nelson Meadows Cottage
Valhalla Cabin in Nelson Meadows
$110 / night
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8 Mi to Jacksonville: Oregon Getaway w/ Deck! Cottage
8 Mi to Jacksonville: Oregon Getaway w/ Deck!
$0 / night
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Jacksonville Towne Square. Cottage
Jacksonville Towne Square.
$0 / night
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Peace and Tranquility! Vineyard Farmhouse Near Britt, Wineries, Shakespeare Agritourism
Peace and Tranquility! Vineyard Farmhouse Near Britt, Wineries, Shakespeare
$0 / night
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