Vacation Home Rentals By Owner In Jacksonville, OR

Showing 31 Of 31 Vacation Rentals

$376.94

Quail Run Mountain View Cottage! Modern Applegate Retreat | River + BLM Access

Jacksonville, Oregon, United States

Escape to a spacious modern retreat in the heart of the Applegate Valley. This newer 3-bedroom cabin features vaulted ceilings, large windows with mountain views, and a short walk to the Applegate River. Backing directly to BLM land for hiking and wildlife, it’s perfect for wine country weekends, fishing trips, family getaways, or a peaceful escape just minutes from Applegate wineries and historic Jacksonville.brbrI’m always available to answer any questions or help in any way I can to ensure you have a smooth and enjoyable stay.brbr• Applegate Valley wineries – minutes awaybr• Historic Jacksonville – short drivebr• Scenic drives, hiking, and river recreation nearbybr• Quiet countryside setting with easy access to townbrbrThe property is located, just minutes from the charming town of Jacksonville, Oregon, and nestled in the heart of the Applegate Valley. This area is known for its scenic beauty, rolling hills, vineyards, and relaxed rural atmosphere, perfect for guests seeking peace, nature, and easy access to local attractions.brbrYou’ll be surrounded by wine country, open landscapes, and fresh country air, while still being close to everything you might need. Historic downtown Jacksonville is only a short drive away and offers restaurants, cafés, boutiques, live music, and seasonal events, including the famous Britt Festival.brbrOutdoor enthusiasts will love the proximity to Applegate River, nearby parks, hiking trails, and Rogue Valley adventures such as rafting, fishing, and swimming. The neighborhood feels quiet and private, making it ideal for unwinding, stargazing, and escaping the pace of everyday life.brbrThis location strikes the perfect balance between seclusion and convenience, a peaceful retreat with quick access to culture, dining, and outdoor recreation.brbrGuests will have exclusive access to the entire cottage.brbrThe SpacebrbrWelcome to our Quail Cottage with a Mountain View, a newly built retreat designed to bring the beauty of Southern Oregon indoors. With vaulted wood ceilings, expansive windows, and a bright open layout, this home offers comfort, privacy, and direct access to the outdoors.brPerfect for families, couples, wine groups, or outdoor enthusiasts looking to experience the Applegate Valley.brbrHighlights Guests Lovebrbr• Mountain and valley viewsbr• Short walk to the Applegate River (visible from the property)br• Direct access to adjacent BLM land for hiking and exploringbr• Peaceful rural setting surrounded by naturebr• New construction with modern finishesbr• Minutes to Applegate wineries and scenic drivesbrbrLiving AreabrbrThe main living space features soaring vaulted ceilings, large windows that fill the home with natural light, and a cozy wood stove for cool evenings. The open layout makes it easy to relax, gather, or enjoy quiet time after a day of exploring.brbrKitchen & Diningbrbr• Fully equipped kitchenbr• Granite countertops and large islandbr• Stainless steel appliancesbr• Coffee maker and essentials providedbr• Dining space for group meals or wine nightsbrbrBedrooms & Comfortbrbr• 3 comfortable bedroomsbr• Quality linens and mattressesbr• Dedicated workspace areabr• Washer and dryer for extended staysbr• Mini-split heating and cooling for year-round comfortbrbrOutdoor & Adventure AccessbrbrThis property is ideal for outdoor recreation:brbr• Walk to the Applegate River for fishing or relaxingbr• Direct access to BLM land for hiking and wildlife viewingbr• Seasonal hunting opportunities available with prior approvalbrbrFew vacation rentals in the Applegate area offer this level of privacy and direct land access.brbrThis property is located along OR-238, making it easy to get around the Applegate Valley and nearby towns.brbrA car is recommended for exploring the area and nearby attractionsbrbrJacksonville is just a short drive away for dining, shopping, and historic sitesbrbrConvenient access to Applegate Valley wineries, outdoor recreation, and scenic drivesbrbrRogue River activities and surrounding attractions are within easy driving distancebrbrTwo separate cabins are located on the property. House #2 is private and fully independent.brbrLooking for more space Ask about reserving both cabins for a private Applegate retreat.brbrProfessionally managed by Siskiyou Stays.

Bed

Bath

Sleeps

Exceptional(2)

$467.92

/ Nightly

Private Vacation Home

-River Retreat Log Cabin w/ Gym, Game Room, and Sauna-

Jacksonville, Oregon, United States

Escape to this beautiful home in Jacksonville, Oregon, located in the heart of the Applegate Forest. Just a short and scenic 5–10-minute walk down to the serene Applegate River, this home is the perfect getaway for your family. In addition to the stunning 19 acres of land to explore, our guests also have full access to the gym/yoga room and game room, as well as the sauna for an additional charge. Our home is fully equipped and comfortable, providing everything you need for a memorable stay.brbrbrThe home is located on the Applegate River Retreat grounds which has over 400 LF of river front access and sits on 19 beautiful acres of lush and serine Applegate Forest! brbrEnjoy a relaxing hike on one of the many trails. You will also have access to the Gym /Yoga Room as well as the Good Vibes Only Game Room at no additional charge! We are neighbors to the Red Lilly Winery and a short drive to Brits Music and Art Festival located in downtown Jacksonville. brbrThe home features:brbr- A remodeled and updated kitchenbrbr- Beautiful living roombrbr- Upstairs master bedroom with a king bed + an En suite bathroombrbr- Main level bedroom with king bedbrbrbrbrKitchen is stocked with: brbr-plates, cups and utensilsbr-microwavebr-ovenbr-potsbr-pansbr-coffee makerbr-blenderbrbrbrAlso added for your convenience:br-hair dryerbr-towelsbr-extra sheetsbr-extra beddingbrbrbrbrPotty-trained pets are allowed. There is a one-time $75 fee per pet. brbrbrWe also have 2 larger homes, as well as 2 RVs, on the property that are available for rent. brbrMain House sleeps 10brMiddle House sleeps 7brRV Campground 1 sleeps 4brRV Campground 2 sleeps 6brbrbrHomes are spread out far apart for privacy. Enjoy a family reunion, stay with friends in the same retreat, or host a corporate event! brbrbrYou and your guests will feel peace and serenity in the extremely beautiful, serene and lush Applegate Forest!

Bed

Bath

Sleeps

Exceptional(2)

$192.25

/ Nightly

Private Vacation Home

NEW Jacksonville Suites - A Pristine Bright 1950s Gem in the of Heart of J-Ville

Jacksonville, Oregon, United States

The NEW Jacksonville Suites is brought to you by the same owner, designer, and host of the five star award-winning Britt Bungalow in Jacksonville Oregon. The Jacksonville Suites is a completely renovated (as of April 2026) historic two-unit 1950’s gem. This is a cheery and very “feel-good” place to relax and have fun during your visit. It’s located in the historic quarter walkable to absolutely everything. Coffee shops, restaurants, parks, hiking trails, trolley rides, grocery store, library, and of course, the world-renowned Britt festivals is just a stroll away. The queen size bed is the #1 rated Dreamcloud mattress with luxury bedding. Desk/vanity in bedroom. The bathroom has a walk-in shower with a Washer/Dryer as well. There is a full kitchen and very comfortable living area with an extra large tv to watch your favorite cable channels or put in your credentials to use Netflix, Amazon Prime, etc… There are lovely benches in front to sip your morning coffee in the sun, or a bistro table to eat your meal under the tree that are yours alone. There is also a magical private fully enclosed backyard space with a dining table as well as lounge chairs to relax all the day long. You will have everything you need supplied for you and will want for absolutely nothing during your stay. So if you’re looking for a thoughtfully designed elevated getaway with mid-century boutique charm… look no further! *Starting September 2026, Jacksonville Suites offers extended month-to-month accommodations.brbrBritt Bungalow: https://www.vrbo.com/7652923ha dateless=true

Bed

Bath

Sleeps

Exceptional(65)

$267.39

/ Nightly

Private Vacation Home

Spacious Forest Home, 3 Bedrooms, Mountain Views, 5 Min. to Jacksonville, Pets!

Jacksonville, Oregon, United States

Perfect roomy house and location for a family gathering, friends getaway or couples retreat. Relax and enjoy the peace and quiet of five acres of serene forest with gorgeous mountain views. Just a mere 5 minutes away from the ultra charming and historic town of Jacksonville with its eclectic mix of restaurants, coffee shops, boutiques, and live music. Numerous and wonderful nearby wineries. Nature lovers will enjoy exploring the many hiking trails. So much to do within easy reach of this lovely property! brbrThis beautiful large 2,600 SF home has forest and/or mountain views from every room. On the main floor is a well appointed and fully equipped kitchen, dining room table seating 6, comfortable living room with TV and cozy gas fireplace for chilly evenings, half bath and primary bedroom with ensuite bathroom and large soaking tub. Two additional bedrooms and a bathroom are upstairs. On the other side of the house with its own staircase is a spacious comfortably furnished media room with a 65 TV. The expansive deck has lounging and eating areas with stunning mountain views. A fun ping pong table is in the garage! Plus PETS are welcome!brbr15% DISCOUNT WITH 7 NIGHT STAY!brbrNote: Hot tub is no longer available

Bed

Bath

Sleeps

Exceptional(75)

$410.06

/ Nightly

Private Vacation Home

Stay in Jacksonville’s iconic 1861 B.F. Dowell House. Walk to Britt Festival, downtown, restaurants, and wine tasting while enjoying stained glass, marble fireplaces, private baths, gardens, and timeless historic charm.

Jacksonville, Oregon, United States

Experience one of Jacksonville’s most iconic historic homes. The beautifully restored 1861 B.F. Dowell House blends original stained glass, marble fireplaces, soaring ceilings, and exposed brick with modern comfort. Located on a large corner lot across from the market and steps from downtown, Britt Festival, restaurants, and tasting rooms. Features private baths for every bedroom, an adjustable Tempur-Pedic bed, clawfoot tub, full kitchen, porch, patio, garden, and lawn.brbrWe are Siskiyou Stays, a local Southern Oregon vacation rental company. We are nearby and available if you need anything during your stay, but we also respect your privacy and want you to enjoy the home at your own pace.brbrGuests can message us through the booking platform at any time with questions or concerns. We are happy to provide local recommendations for restaurants, wineries, hiking, Britt Festival events, and things to do in Jacksonville and the surrounding Rogue Valley.brbrThe B.F. Dowell House is located on a large corner lot in the heart of historic Jacksonville, directly across from the local market and only steps from downtown.brbrThis charming neighborhood is known for its tree-lined streets, beautifully preserved architecture, boutique shops, tasting rooms, coffee shops, and welcoming small-town atmosphere.brbrGuests can easily walk to:brbrBritt Festival concerts and eventsbrJacksonville restaurants, cafes, and wine tasting roomsbrHistoric downtown shops and landmarksbrThe local market directly across the streetbrbrSome local favorites include dinner at Jacksonville Inn, coffee at GoodBean Coffee, and wine tasting at South Stage Cellars.brbrDespite being so close to everything, the neighborhood remains quiet, peaceful, and residential, making it easy to relax after a day exploring Jacksonville and the Rogue Valley.brbrGuests have full private access to the entire home, porch, patio, lawn, and gardens.brbrThis includes:brbrAll bedrooms and bathroomsbrLiving room and sitting areasbrKitchen and dining spacesbrLaundry roombrOutdoor spaces and gardenbrPatio with outdoor seatingbrCharcoal BBQbrCroquet setbrbrA guest information binder with the Wi-Fi password, TV instructions, and local recommendations is located on the kitchen counter.brbrThe B.F. Dowell House is a rare blend of historic architecture and modern comfort. Designed for both gathering and privacy, the home features spacious common areas, multiple sitting rooms, and private bathrooms for every bedroom.brbrLiving Areas:brbrSpacious living room with an original marble fireplacebrAdditional sitting areas perfect for conversation, reading, or relaxingbrSoaring ceilings, abundant natural light, exposed brick, and stained-glass details throughoutbrbrBedrooms & Bathrooms:brbrSpacious bedrooms with elegant furnishingsbrPrivate full bathroom adjoining each bedroombrAdjustable Tempur-Pedic bed in the primary suitebrClassic clawfoot soaking tubbrHistoric charm paired with modern comfort and privacybrbrKitchen & Dining:brbrLarge, fully equipped kitchen with cookware and essentialsbrPlenty of prep space for group meals and extended staysbrDining area ideal for gathering togetherbrCozy porch directly off the kitchen overlooking the propertybrbrOutdoor Space:brbrPrivate patio with outdoor seatingbrSpacious lawn and gardensbrCharcoal BBQbrCroquet set for classic outdoor funbrbrOne of the best parts of staying at the B.F. Dowell House is how walkable everything is.brbrYou can easily walk to:brbrDowntown JacksonvillebrBritt FestivalbrRestaurants and coffee shopsbrWine tasting roomsbrBoutique shoppingbrThe grocery market directly across the streetbrbrA car is not necessary if you plan to stay in Jacksonville itself. Free parking is available at the home.brbrIf you would like to explore more of Southern Oregon, the home is conveniently located:brbrApproximately 15 minutes from the Medford airportbrAbout 20–25 minutes from Ashland and the Oregon Shakespeare FestivalbrA short drive to Applegate Valley wineriesbrNear Rogue River recreation and hiking trailsbrAbout 2 hours from Crater Lake for an unforgettable day tripbrbrOriginally built in 1861, the B.F. Dowell House has been lovingly restored and preserved by the Hartman family since 1910. Historic photographs throughout the home showcase the home's remarkable 20-year restoration and the family's long history with the property.brbrThis home is ideal for Britt Festival guests, wedding groups, wine country vacations, family gatherings, girls’ weekends, couples traveling together, and extended stays.brbrHouse Rules & Important Information:brbrNo smoking or vaping anywhere on the property.brFireplaces are decorative only unless specifically noted otherwise.brPlease do not move historic furnishings, artwork, or photographs.brQuiet hours are from 10:00 PM to 8:00 AM.brPlease remove shoes indoors to help preserve the historic floors.brIf pets are allowed for your reservation, they must be disclosed and approved in advance.brThe market directly across the street is perfect for groceries, wine, and essentials during your stay.brbrPlease note: All reservations require completion of a pre-arrival registration form, submission of a valid government-issued photo ID for the primary guest, and signing of our rental agreement prior to check-in. For reservations made outside of Airbnb, guests are also required to place a valid credit card on file for a refundable security hold. The card will only be charged, if necessary, under the terms of the rental agreement. Check-in instructions and access information will be provided once these steps are completed.

Bed

Bath

Sleeps

$319.39

/ Nightly

Private Vacation Home

Sun Cottage in the Heart of Jacksonville

Jacksonville, Oregon, United States

Escape to beautiful Jacksonville and enjoy a relaxing stay in this bright and spacious 2-bedroom, 1-bathroom cottage, ideally located just minutes from the heart of town. Whether you`re visiting for a weekend getaway, wine tasting, Britt concerts, or outdoor adventures, this charming home offers the perfect blend of comfort and convenience.brbrStep inside to an inviting, light-filled living space designed for relaxing after a day of exploring. The open layout creates a warm and welcoming atmosphere for gathering with friends or family. The fully equipped kitchen has everything you need to prepare meals at home, whether it’s a quick breakfast before heading out or a cozy dinner in.brbrUnwind in the evenings with live TV or stream your favorite shows for a laid-back movie night. Comfortable bedrooms provide a peaceful retreat so you can recharge for another day of summer fun.brbrLocated just a short stroll from historic downtown Jacksonville, you’ll have easy access to boutique shopping, local restaurants, wine tasting rooms, and seasonal events. Spend your days exploring nearby hiking trails, enjoying outdoor recreation, or simply soaking in the charm of this historic town.brbrTraveling with pets We welcome your furry companions — this is a pet-friendly stay so the whole family can enjoy your time away.brbrBook your stay and experience the charm, comfort, and unbeatable location of this delightful Jacksonville cottage!

Bed

Bath

Sleeps

Exceptional(10)

$263.91

/ Nightly

Private Vacation Home

Red Barn in Wine Country

Jacksonville, Oregon, United States

Brand new luxury barn with a rustic feel on Red Barn Farm in Southern Oregon Wine Country. Our five-acre micro-farm is located on the Applegate River on the Applegate Wine Trail, a region of 19 artisan wineries. There's a bridge to the world famous Red Lily Vineyard, right on our property! At Red Barn Farm, we have a river swimming hole, friendly farm animals, and a fire pit to spend dreamy evenings under the stars. Visit Wine Country Farm Stay dot com for more info!brbrGuest accessbrBarn, fire pit, pasture and riverfront are all accessible to guests. During business hours, Red Lily Vineyard is also accessible.brbrAdditional rulesbrNO SMOKING: This is a smoke-free property. br brbrHEAT & AC: The barn has a mini-split system on both floors. In the winter, please adjust the heat down to 60 degrees when you leave. In the summer please turn the AC off when you leave.brbrbrPET POLICY: br1. Only one animal allowed. Pet fee is $25 per staybr2. Please pick up and dispose of all pet droppings on the property.br4. Dogs must remain on leash to protect our free-range chickens.br5. The trundle bed is NOT a pet bed. It is for human use only.brbrbrRED LILY VINEYARDS:brGuests are able to enjoy Red Lily Vineyards daily from 11:00 am to 5:00 pm May 1 – October 31 and November 1 – April 30, Thursday – Sunday. Please respect business hours. Do not enter their property when they are not open, nor linger after hours.brbrGATHERING: If guests invite family or friends to enjoy the property/river with them, they must notify the host and pay a $20 fee per guest. A maximum of four extra guests ($80) are allowed at any one time.brbrBefore you leave:br- Throw rubbish awaybr- Lock upbr- Please wash and dry dishes.

Bed

Bath

Sleeps

Exceptional(7)

$275.15

/ Nightly

Private Vacation Home

Kubli Haus - Suite #4 ~ Luxury, Style & Location, 1 block to Britt

Jacksonville, Oregon, United States

Suite #4 is the most peaceful and quiet accommodation of the 5 vacation rental units at Kubli Haus. Located on the second floor, it's just a few steps up the grand circular staircase from the front entry. From your bed, enjoy serene views of mature fig trees, lush forest, and magnolias. Inside, take in the detail of the rustic shiplap ceilings and restored 160-year old fir wood floors.brbrA queen-sized bed anchors the common bedroom/living space, which also includes a kitchenette, wingback chair, metral drum side-table and a wall-mounted 4k UHD TV with cable and streaming capabilities. The en suite bathroom boasts a large walk-in tile and glass shower, and a vanity with oversized antique mirror. Laundry facilities are also available on-site for guest use.brbrThis suite is best suited for the single traveler or a couple looking for peace, quiet, and coziness. If you are looking for more capacity, additional suites or the entire house may be rented out for larger group sizes up to 14 people. Inquiries can be made directly with the host.brbrAll suites at Kubli Haus have smart-lock features, therefore, guests have the option of contactless or in-person check-in.brbrLocation! Location! Location!brKubli Haus is located in the Historic District of Jacksonville, just one block away from the Britt Festival grounds and numerous hiking trails and two short blocks from the coffee shops, wine tasting rooms, bars, restaurants and boutiques that line California Street.brbrPorch Culture Revived!brRelax on the floating bench or cushioned seats which line the signature wrap-around porch. Enjoy your morning coffee or a glass of wine, watch the townsfolk pass by and experience Jacksonville like a local. Didn’t get your Britt tickets That’s Ok, enjoy the concert one block away from the porch, patio, or lawn.br

Bed

Bath

Sleeps

Exceptional(9)

$302.77

/ Nightly

Private Vacation Home

Kubli Haus - Suite #1, Kubli Haus - Suite #1 ~ Luxury, Style & Location, 1 block to Britt

Jacksonville, Oregon, United States

Suite #1 is the most spacious of our suites at 550 square feet. Located on the ground floor, it has direct access to the wrap-around porch. brbrFeatures include king-size bed in bedroom, queen-size sofa bed in living room, rooms are separated by historic pocket doors. Each room is equipped with its own wall-mounted 4k UHD TV with cable and streaming capabilities. In the living area there is a kitchenette with mini fridge, microwave, Keurig coffee maker, sink with filtered water and dishes/silverware. The ensuite bathroom has a walk-in shower, dual sinks, and a water closet. brbrbrbrThis suite is ideal for single person, one couple, two couples or a small family (extra charges apply for more than 2 guests). brbrbrbrAll suites at Kubli Haus have smart-lock features, filtered drinking water, black out shades and/or curtains, kitchenettes/kitchen, coffee and creamer, dedicated parking space.

Bed

Bath

Sleeps

Exceptional(11)

$297.25

/ Nightly

Private Vacation Home

Kubli Haus - Suite #2 ~ Luxury, Style & Location, 1 block to Britt

Jacksonville, Oregon, United States

Suite #2 is one of the most spacious of our 5 vacation rental units at Kubli Haus. It is on the ground floor, with direct access to the wrap-around porch. True to the home's Victorian style, this suite has 10-foot ceilings and tall windows. The open layout of this suite and good southern exposure combine to provide lots of natural light. Guests also have the option of using the privacy shades and black out curtains installed on all windows.brbrIn the combined bedroom/living space, there is a king-size four poster bed along with a queen-size pull-out sofa bed. The large wall-mounted 4K UHD TV has cable and streaming capabilities and can swivel to face the bed or couch. A kitchenette is provided with full size fridge for those who prefer longer stays and there is also a breakfast/work table provided next to the porch window. brIn the bathroom, a glass-enclosed walk-in shower showcases the classic vertically-stacked tiling on the walls. Double sinks and oversized mirrors occupy the vanity space. Laundry facilities are also available on-site for guest use.brbrThis suite is ideal for one couple, two couples or a small family (extra charges apply for more than 2 guests), professional work/travel and those looking for a big bed, more room, more privacy, and an extremely quiet location. If you are looking for more capacity, additional suites or the entire house may be rented out for larger group sizes up to 14 people. Inquiries can be made directly with the host.brbrAll suites at Kubli Haus have smart-lock features, therefore, guests have the option of contactless or in-person check-in.brbrLocation! Location! Location!brKubli Haus is located in the Historic District of Jacksonville, just one block away from the Britt Festival grounds and numerous hiking trails and two short blocks from the coffee shops, wine tasting rooms, bars, restaurants and boutiques that line California Street.brbrPorch Culture Revived!brRelax on the floating bench or cushioned seats which line the signature wrap-around porch. Enjoy your morning coffee or a glass of wine, watch the townsfolk pass by and experience Jacksonville like a local. Didn’t get your Britt tickets That’s Ok, enjoy the concert one block away from the porch, patio, or lawn.br

Bed

Bath

Sleeps

Exceptional(5)

$340.35

/ Nightly

Private Vacation Home

Studio 5 at Kubli Haus

Jacksonville, Oregon, United States

Studio 5 at Kubli Haus is located in the rear of the building with its own private entrance, a private courtyard and a designated parking space in the driveway. This unit has a sportier vibe than our other 4 suites. It's an open concept studio with full size kitchen, small dining area, living room, alcove with queen size bed and a bathroom with shower. The living room features a wall mounted Smart 4K UHD TV. The private courtyard is fully fenced and screened from public view, with gas BBQ and illuminated seating area.brStudio 5 is ideal for visitors, business travelers, or vacationing couples looking for an extended stay up to 45 days.brThe full kitchen and private courtyard creates the ideal hub for larger group stays and whole house rental for up to 14 people. Please inquire directly for rates and availability.

Bed

Bath

Sleeps

Rent a place that suits your needs

Bed

Bath

Sleeps

Exceptional(5)

$192.25

/ Nightly

Private vacation home

NEW Jacksonville Suites - A Pristine Bright 1950s Gem in the of Heart of J-Ville

Jacksonville, Oregon, United States

Bed

Bath

Sleeps

Exceptional(5)

$112.16

/ Nightly

Apartment

Private suite in Historic Jacksonville's I930's Log home. Pet friendly.

Jacksonville, Oregon, United States

Bed

Bath

Sleeps

Exceptional(5)

$133.13

/ Nightly

Cottage

Cozy private family ranch cottage! Vineyards, Britt Festival and Applegate Lake!

Jacksonville, Oregon, United States

Bed

Bath

Sleeps

Vacation Home Rentals By Owner In Jacksonville, OR

$376.94

$467.92

$192.25

$267.39

$410.06

$319.39

$263.91

$275.15

$302.77

$297.25

$340.35

Rent a place that suits your needs

Most popular vacation rentals in Jacksonville

$188.64

$216.58

$214.37

$214.18

$202.66

$197.68

$194.03

$192.25

$112.16

$133.13

Most Popular Cities in Oregon