Voted as one of the top ten coolest small towns in America, Jacksonville is a great vacation destination for all. This historic landmark offers more than just a rich cultural experience or a walk down memory lane in history. Visitors can also expect to spend a few days of wine-tasting and exploring the many vineyards and wineries in Jacksonville. There are also plenty of hiking and biking trails for nature-lovers, and to take in the beautiful sights of Oregon. Be sure to come during the Britt Music Festival, and bask in the company of world-class musicians of all eras. This three-weekend music festival stands as an iconic highlight of Jacksonville, and is not to be missed! It is hard to refuse such a treat while being surrounded by the spectacular beauty of Southern Oregon. Enjoy a little respite on your vacation, and even more so with these top Airbnbs in Jacksonville, Oregon.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on December 18, 2024.
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1. Quaint, cozy apartment (from USD 76)
Located near downtown Medford in a commercial neighborhood, this cozy apartment offers a scenic view of the distant hills. Also, it is conveniently located with access to the airport (2 miles/3.2 kilometers away), as well as downtown Jacksonville (5 miles/8 kilometers), and Ashland (10 miles/16 kilometers). It is only a block away from The Pallet Winery, and a couple of blocks from cafes and theatres. This pet-friendly apartment offers a comfortable stay for up to four guests, with a queen-sized bed in the bedroom, as well as a sleeper sofa bed in the living room. Also, breakfast will be provided for guests.
2. Chic bungalow-type accommodation in the heart of Jacksonville (from USD 245)
Situated in the heart of Jacksonville where you can find most of the city’s top visited establishments, from excellent restaurants to bars and cafes to retail shops, souvenir stores, and others, this vacation rental is a convenient and cozy place to stay in Oregon. It has bright furnishings and a cool and airy ambiance. It can accommodate up to four guests, featuring two chic and comfy bedrooms, two charming private bathrooms with bathtubs, a modern kitchen, a lovely dining space, a comfortable living room, a laptop-friendly workspace, and a patio.
Top guest reviews
Host:
top shelf place top shelf hostthe host was super helpful and accommodatingthank you for being such a great host this was a lovely staytammy was extremely accommodating with our check in requests and had great suggestions for local mealsbeautiful bungalow comfy bed super nice and responsive hostLocation:
the location is excellentgreat location easy walk to downtownthe location is ideal as wellit is a very easy walk to the main street stores and food placeswonder place to stay close to everything yet quiet and relaxingCleanliness:
the house is exactly same as picture even better very quiet clean and delicate placethe house was very clean nicely decorated and stocked with all that we neededtammy's place is fantastic super clean nice touches w flowers and the location is perfectRead more reviewsAmenities & Room:
the cottage is cozy with a lovely patio and front yardfresh flowers were also on the table to greet youthe cottage was light bright comfortable and overall adorablekitchen was well stocked living space was plentiful outdoor patio(s ) were greatthe bathrooms are beautiful and well stocked
3. Cozy Jacksonville cottage (from USD 65)
Live in comfort in this Jacksonville vacation rental. Located near downtown Jacksonville, this cozy one bedroom cottage is an ideal choice for solo travelers, couples, and friends. It is only a 15-minute walk to downtown Jacksonville, and half an hour away from Ashland. The cottage offers a bedroom that sleeps up to two guests, alongside a private bathroom. Guests are welcome to use the living room area, as well as the small patio area. The cottage has a kitchenette with sink, fridge, microwave, hot plate, and kettle. Essentials are provided for guests in order to ensure their stay is an enjoyable one.
Top guest reviews
Host:
excellent hospitality and super nice host 5-starsshe’s a wonderful hostwonderful retreat and awesome hostthe host is very nice and consideratethe host was wonderful and there were some excellent restaurant recomendations availableLocation:
very cute cozy place near the edge of townnice garden and great locationlocation was great and close enough to walking trails and downtown if you’re a fairly good walkernicely designed unit at a good location near to town centerthis is a cute little house tucked away on a very quiet residential streetCleanliness:
her place was clean and comfortableeverything’s so clean and organizedit was spacious enough for the two of us and our dog clean and well stockedmaryl’s cottage was very clean and cozynice little cottage with fresh made cookies was clean and a relatively short walk to townRead more reviewsAmenities & Room:
the courtyard is lovely to sit in and the bed was comfortablethe cottage was very cute and comfortablethe cottage is stylish and cozy and much more better than on the photosthe bed was comfy and the heater works greatmaryl is a great host and her cottage is cozy and has necessary amenities
4. Plymale Cottage (from USD 135)
There is no better place to experience the pristine nature of Jacksonville than in this vacation rental. Located in the heart of Jacksonville, this Plymale cottage is a promising place for guests who want to experience the wildlife in Jacksonville. Be surrounded by the beauty of nature in this historic town - oak trees, pine trees, and exquisite wildlife while enjoying a cup of coffee or a glass of wine in the evening on the cozy guest balcony. It’s an ideal accommodation with ample comfort that can even soothe the children to sleep. The cottage provides a king-sized bed, a queen-sized bed and a sofa bed that sleeps up to four guests in total. A Bosh child’s fold-down bed that accommodates children up to three years old is also available upon request. Keep the children at play with the toys in the Hobbit Room.
Top guest reviews
Host:
loni was a wonderful hostloni is a delightful hostshe is kind and a wonderful hostloni was a wonderful and attentive hostloni was a five star host and super warm and lovelyLocation:
the location is perfectthe location is perfect and within walking distance to everythingthe location walking distance to downtown and the britt festival is idealwalkable location to town and britt festivalthe location was perfect alsoCleanliness:
apartment is big and clean and comfortableeverything was as described; clean and comfortablethe upstairs apartment was private clean and cozythe rooms are spacious clean and well appointedeverything was very clean and the breakfast (biscotti and fruit) was tasty each morningRead more reviewsAmenities & Room:
lovely balcony for breakfast coffee or evening winewe really appreciated the air conditioning as the temp soared over 100 degreesit's already a quiet neighborhood but with the fan we didn't hear a thingthe homemade breakfast treats were very tasty and much appreciatedthe breakfast was delicious home made pastries good coffee and kept in hot thermoses
5. Historical carriage house
Located on the property of the historical 1968 Jacksonville home, this modern cottage offers guests a unique vacation homestay experience in Jacksonville. It is conveniently located from the center of the town (only two blocks away) as well as the Britt grounds. There is no better place for Britt concert-goers to experience the thrilling music festival and the heart of historic Jacksonville in this perfect location. Also, it is only twenty minutes away from Ashland. Experience your vacation in luxury-style and soak in the hot tub after a long day of activity. Guests are welcome to use the private patio and indoor fireplace as well.
Jacksonville, Oregon, United States
354 meters (0.3 ft) from Doc Griffin ParkAccommodates: 2
Top guest reviews
Host:
bobbi is a great hostbobbi was a great hostbobbi was great host to work withperfect base for exploring jacksonville and a lovely hostbobbi is a great host and very welcomingLocation:
great location just a short walk to townthe location is nice and the town is cutegreat location and adorable accommodationwe loved this location and the spacesuper convenient location to everything in javksonvilleCleanliness:
it was super clean quaint and attractivebathroom was new and clean and the bed was comfortablethe bed was so comfortable very clean and privatevery clean and easy check in/outbarbara's house was extremely cleanRead more reviewsAmenities & Room:
would definitely recommend mattress heater and space heater in bathroom were a nice touchthe cottage is appointed with a wonderful bed excellent mattressthe "carriage house" was extremely comfortable with large king mattress and wonderful spa tubthe bed was very comfortable lots of warm soft blankets and the heater was greatcomfy cozy and air conditioning nice private space
6. Stunning vacation rental (from USD 189)
If you are looking for an affordable, cozy, and convenient accommodation in Jacksonville, then this property might be the one for you. It showcases stylish and chic country-style interiors and delightful amenities. It can accommodate up to six guests, featuring two charming bedrooms, a private bathroom, a kitchen equipped with cooking essentials, a dining room with a fabulous table setting, a comfortable living room with a fireplace, a patio, and a manicured lawn where the kids can run around and play.
Top guest reviews
Host:
thank you for being a great host stephaniehouse owner provided us with tons of great recommendationsstephanie is a thoughtful accommodating host and her home is warm inviting and comfortableand the host stephanie is super greatgreat house and immecable hostsLocation:
great location for downtown ashlandperfect location to walk to everythingperfect location great hostessgreat place and great locationthe location is great for walking to downtown jacksonvilleCleanliness:
very nice clean and convenient placethe house was impeccably cleanit felt very cleanvery comfortable and cleancozy comfortable convenient & cleanRead more reviewsAmenities & Room:
the amenities are too numerous to list i highly recommended this lovely and comfortable propertybeds were super comfortablea beautiful cozy cottage in the heart of jacksonvillethis is a lovely and comfortable home well represented by the photos and descriptionthe bed was comfortable & the sheets were soft
7. Beautiful and luxurious cottage (from USD 208)
This luxury cottage is a cozy getaway house with delightful amenities. It showcases a beautifully furnished home with muted color palette furnishings and a cool and airy ambiance that is homey in nature. It houses two charming bedrooms, a full private bathroom, a modern kitchen where you can release your inner culinary expert, a dining space, a cozy living room with expansive windows, comfortable couch seats, a flat-screen TV, and an outdoor seating area with a fire pit.
Top guest reviews
Host:
she is a great hostjackie was also a great host responded quick and made us feel welcomejackie is also a wonderful host who is quick to respond to any questionsjackie was an excellent host highly recommendedjackie was a responsive and generous hostLocation:
great location just a short walk to everything in townthe location was an easy walk to downtown jacksonvilleeasy walk to enjoy jacksonvillethis spot is an amazing location to walk into the heart of jacksonvillevery quiet and safe and super easy walking distance to downtownCleanliness:
everything is new and so clean and freshas before everything was clean and neathad a great stay comfortable clean and great communicationthe house is clean comfortable and very stylishvery clean fully stocked with everything and moreRead more reviewsAmenities & Room:
comfortable bed nice linens and reliable internetthe cottage was perfect for 2 couples plenty of room and an open floor planbeds: amazingly comfortable bed/linenshair products lotions toiletries iphone outlets in every room fluffy beautiful robesthe little town of jacksonville has restaurants and great coffee shops/breakfast places a quick walk from the house
8. Luxurious cottage (from USD 208)
Conveniently located in historic Jacksonville, this remodeled luxurious two-bedroom cottage is an ideal choice for all travelers. Be surrounded by the beautiful scenery of Southern Oregon. It has great access to restaurants, shopping, vineyards, wineries, hiking trails and beautiful parks. It is a perfect getaway vacation experience in Jacksonville. Guests will have the entire cottage to themselves, alongside private parking. This luxurious cottage offers a king-sized bed, a queen-sized bed, and a floor mattress. There is a beautifully tiled bathroom that offers all the necessary amenities. Feel free to use the private yard and cozy fire pit anytime!
Top guest reviews
Host:
she is a great hostjackie was also a great host responded quick and made us feel welcomejackie is also a wonderful host who is quick to respond to any questionsjackie was an excellent host highly recommendedjackie was a responsive and generous hostLocation:
great location just a short walk to everything in townthe location was an easy walk to downtown jacksonvilleeasy walk to enjoy jacksonvillethis spot is an amazing location to walk into the heart of jacksonvillevery quiet and safe and super easy walking distance to downtownCleanliness:
everything is new and so clean and freshas before everything was clean and neathad a great stay comfortable clean and great communicationthe house is clean comfortable and very stylishvery clean fully stocked with everything and moreRead more reviewsAmenities & Room:
comfortable bed nice linens and reliable internetthe cottage was perfect for 2 couples plenty of room and an open floor planbeds: amazingly comfortable bed/linenshair products lotions toiletries iphone outlets in every room fluffy beautiful robesthe little town of jacksonville has restaurants and great coffee shops/breakfast places a quick walk from the house
9. Luxury cottage in Jacksonville's historic core (from USD 193)
Located in the historic area of Jacksonville, this charming vacation rental is a delightful haven that will make your vacation more cozy and convenient. With perfectly manicured lawns and a lovely garden, guests will definitely love the vibes of the quiet and peaceful neighborhood. It features a French country style interior design, housing a charming bedroom, a lovely private bathroom, a farmhouse-inspired kitchen with an adjacent dining area, and a fabulous living room space with lots of natural light. Plus, there’s an available parking space for guests traveling by their car.
Top guest reviews
Host:
jackie always provided a quick response to our many questions and lots of helpful tipsjackie is the best most kind and thoughtful hostjackie is an amazing host her home reveals how she has thoughtfully prepared for your stayamazing place to stay and great hostit is beautiful she is an exceptional host and we feel pampered staying at her propertiesLocation:
the location is perfectwithin walking distance of shopping and the britt festivallocated right downtown we were able to walk to eat and to stores easilyrental was beautiful perfect location gorgeous decorsuch a great place and perfect locationCleanliness:
the place was clean and airy very fresh smelling with wonderful comfortable bedding and towelsit’s a clean and aesthetically pleasing homeRead more reviewsAmenities & Room:
the furniture was all very comfortable especially the bedit’s fashionable and very very comfortable
10. Apartment near Britt Grounds
Look no further, concert-goers! This apartment is conveniently located just four blocks away from the Britt grounds - an ideal choice for all travelers, even families with babies! It lies in a quiet street, yet is within close proximity to bars and restaurants and everywhere in Jacksonville. This Jacksonville, Oregon rental offers guests a comfortable stay in the master bedroom with a king-size bed, a sleeper sofa bed in the living room, and a private bathroom. Guests are welcome to use the kitchen to cook their own meals.
Jacksonville, Oregon, United States
92 meters (302.1 ft) from Doc Griffin ParkAccommodates: 4
Top guest reviews
Host:
bruno is a great hostbruno is a great hostbruno is a wonderful hostbruno is a great host he has gone above and beyond our expectationsbeautiful town and a most gracious hostLocation:
great location and cute spaceamazing location for the britt walkawesome location great little placegreat location near the brittwonderful apartment located close to the brittCleanliness:
super clean and quite houseextremely clean and lightit was clean and very comfortableclean functional guest houseultra clean and extremely comfortable bedRead more reviewsAmenities & Room:
there was no tv (unexpected) but good internet connection/wi-fiking size bed with heated pad was awesomethe apartment looks exactly like the photos—spacious light and airy and well appointedthe bed is very comfortable the bathroom is spacious with lovely views of the trees from the showerthe living area and kitchen are open and get great light
11. Gorgeous house close to downtown
For a fabulous stay in Jacksonville, rent this gorgeous house that offers a range of amazing amenities. Guests have access to a lovely pool, a spa, a garden, outdoor seating, and more. Inside, the fully furnished house has a well-appointed living room, cozy bedrooms, full bathrooms, an elegant dining room, a screened-in porch, and a well-equipped kitchen. Downtown Jacksonville is just two blocks away, where you can easily access the restaurants, shops and pubs of the area.
Jacksonville, Oregon, United States
85 meters (279.3 ft) from Doc Griffin ParkTop guest reviews
Host:
absolutely gorgeous home with top rate hoststhey are great hostsjulie and jeff are great hostscouldaccommodate a large party we enjoyed meeting them and they were very helpfuljeff and julie are the absolute best they are warm and friendly hosts who have thought of everythingLocation:
the location is very close shops and good restaurantscute place that is close to everything in jacksonvillethe location of the home is perfect short walk to the main strip in jacksonvillebeautiful home in a great locationthe many near by eating places a bonus thanks againCleanliness:
the place was beautiful and nice and clean it was a descent trip overallthe cottage and house were sparkling clean and full of decorator accentsclean comfortable period victorian with lots of new things to find and old things to enjoytheir home was squeaky clean and the location can’t be beatRead more reviewsAmenities & Room:
the view from the pool is fantasticthe pool and outdoor grilling/drink mixing/lounging space are better than any hotellots of amenities would have loved to be there earlier in the year to use the poolpool patio and outdoor kitchen was perfect for lounging and cooking all day by the poolgreat place with plenty of room for our group
12. Beautiful Jacksonville apartment
Conveniently located near Historic Jackson, this beautiful apartment also offers great access to the wineries, Applegate river and lake, Rogue River and Ashland (20 minutes’ drive). It is also near the Britt grounds but guests must be able to walk up the hill. This private daylight basement apartment offers guests a cozy stay with two single beds and a private bathroom. Guests will have access to the outdoor swimming pool in the summer, as well as the outdoor patio. It is a wonderful place to enjoy tranquility and have an enjoyable vacation!
449 meters (0.3 ft) from Doc Griffin Park
13. Cozy guesthouse
Located within walking distance to the historic Jacksonville district, this cozy guesthouse offers guests a comfortable stay. It is also near the Britt grounds, as well as wineries and restaurants. This place provides for guests a queen-sized bed, and another queen-sized air mattress if needed, and a private bathroom. Guests are welcomed to use the lounge/living room, kitchen, dining room, back patio, and yard. Also, feel free to borrow beach towels, picnic basket or blanket whenever needed.
404 meters (0.3 ft) from Doc Griffin Park
14. Table Rock Room at TouVelle House B&B
Located near the Britt grounds, the TouVelle House is a bed and breakfast guest house in historic Jacksonville. It has easy access to shops, restaurants, wineries and only a half-hour from Ashland. It is also the perfect launching point for spectacular day-trips to Crater Lake, Oregon Caves, and Redwood National Park. The guest room is located on the first floor, offering easy access to all of the common rooms, and close proximity to coffee and fresh baked cookies. Should you opt to stay indoors, you will have plenty to keep yourself entertained with at TouVelle House. There is a bocce ball court, library game room, business center, swimming pool, and even an indoor fireplace for a cozy read or conversation.
602 meters (0.4 ft) from Doc Griffin Park
15. Cozy and serene guesthouse
Conveniently located near historic Jacksonville, this peaceful and secluded guest house is great for retreats, getaways or to enjoy the scenic beauty of Southern Oregon. It is a perfect choice for solo adventurers, couples, and nature-lovers with many wineries and outdoor hikes that are in close proximity to explore. Sit near the indoor fireplace and enjoy a book or conversation for a cozy time of relaxation. Be in absolute comfort as you rest your head each night, and gear yourself up for another day of exploration.
Jacksonville, Oregon, United States
1.95 km (1.3 mi) from Doc Griffin Park
Rest, recharge, revisit!
Take in the sights of the hills, bask in the golden rays of the sun by the river or lake, learn about the history of this quaint town, savor the different tastes of the wineries and vineyards, treat your ears to an array of timeless music arrangements. Jacksonville, in all its scenic beauty and rich cultural experiences, invites travelers to unwind and recharge. Once you’ve seen Jacksonville, you are sure to be visiting quite often. And whether you’re looking for accommodations in town or lodging near Jacksonville, Airbnb has you covered!
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