Top 15 Airbnb Vacation Rentals In Jacksonville, Oregon

airbnb Jacksonville Oregon
Lilian
Lilian 
Updated
| 7 min read

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 March 02, 2024.

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.


7.55 km (4.7 mi) from Doc Griffin Park
552 reviews  
Entire apartment 2 Beds 4 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.

Stayed at this property?
Jacksonville, Oregon, United States
493 meters (0.4 ft) from Doc Griffin Park
246 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 5 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 5

Top guest reviews
Amenities & Room:
the cottage is cozy with a lovely patio and front yard
fresh flowers were also on the table to greet you
the cottage was light bright comfortable and overall adorable
kitchen was well stocked living space was plentiful outdoor patio(s ) were great
the bathrooms are beautiful and well stocked
Cleanliness:
the house is exactly same as picture even better very quiet clean and delicate place
the house was very clean nicely decorated and stocked with all that we needed
tammy's place is fantastic super clean nice touches w flowers and the location is perfect
Host:
top shelf place top shelf host
the host was super helpful and accommodating
thank you for being such a great host this was a lovely stay
tammy was extremely accommodating with our check in requests and had great suggestions for local meals
beautiful bungalow comfy bed super nice and responsive host
Location:
the location is excellent
great location easy walk to downtown
the location is ideal as well
it is a very easy walk to the main street stores and food places
wonder place to stay close to everything yet quiet and relaxing
Read more reviews

3. Cozy Jacksonville cottage

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.

Stayed at this property?
Jacksonville, Oregon, United States
1.34 km (0.9 mi) from Doc Griffin Park
889 reviews   Superhost Wifi Available
Entire guesthouse 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the courtyard is lovely to sit in and the bed was comfortable
the cottage was very cute and comfortable
the cottage is stylish and cozy and much more better than on the photos
the bed was comfy and the heater works great
maryl is a great host and her cottage is cozy and has necessary amenities
Cleanliness:
her place was clean and comfortable
everything’s so clean and organized
it was spacious enough for the two of us and our dog clean and well stocked
maryl’s cottage was very clean and cozy
nice little cottage with fresh made cookies was clean and a relatively short walk to town
Host:
excellent hospitality and super nice host 5-stars
she’s a wonderful host
wonderful retreat and awesome host
the host is very nice and considerate
the host was wonderful and there were some excellent restaurant recomendations available
Location:
very cute cozy place near the edge of town
nice garden and great location
location was great and close enough to walking trails and downtown if you’re a fairly good walker
nicely designed unit at a good location near to town center
this is a cute little house tucked away on a very quiet residential street
Read more reviews

4. Plymale Cottage

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.

Stayed at this property?
Jacksonville, Oregon, United States
223 meters (0.2 ft) from Doc Griffin Park
258 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
lovely balcony for breakfast coffee or evening wine
we really appreciated the air conditioning as the temp soared over 100 degrees
it's already a quiet neighborhood but with the fan we didn't hear a thing
the homemade breakfast treats were very tasty and much appreciated
the breakfast was delicious home made pastries good coffee and kept in hot thermoses
Cleanliness:
apartment is big and clean and comfortable
everything was as described; clean and comfortable
the upstairs apartment was private clean and cozy
the rooms are spacious clean and well appointed
everything was very clean and the breakfast (biscotti and fruit) was tasty each morning
Host:
loni was a wonderful host
loni is a delightful host
she is kind and a wonderful host
loni was a wonderful and attentive host
loni was a five star host and super warm and lovely
Location:
the location is perfect
the location is perfect and within walking distance to everything
the location walking distance to downtown and the britt festival is ideal
walkable location to town and britt festival
the location was perfect also
Read more reviews

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.

Stayed at this property?
Jacksonville, Oregon, United States
354 meters (0.3 ft) from Doc Griffin Park
160 reviews   Wifi Available
ENTIRE HOME 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
would definitely recommend mattress heater and space heater in bathroom were a nice touch
the cottage is appointed with a wonderful bed excellent mattress
the "carriage house" was extremely comfortable with large king mattress and wonderful spa tub
the bed was very comfortable lots of warm soft blankets and the heater was great
comfy cozy and air conditioning nice private space
Cleanliness:
it was super clean quaint and attractive
bathroom was new and clean and the bed was comfortable
the bed was so comfortable very clean and private
very clean and easy check in/out
barbara's house was extremely clean
Host:
bobbi is a great host
bobbi was a great host
bobbi was great host to work with
perfect base for exploring jacksonville and a lovely host
bobbi is a great host and very welcoming
Location:
great location just a short walk to town
the location is nice and the town is cute
great location and adorable accommodation
we loved this location and the space
super convenient location to everything in javksonville
Read more reviews

6. Stunning vacation rental

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.

Stayed at this property?
Jacksonville, Oregon, United States
307 meters (0.2 ft) from Doc Griffin Park
244 reviews   Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
the amenities are too numerous to list i highly recommended this lovely and comfortable property
beds were super comfortable
a beautiful cozy cottage in the heart of jacksonville
this is a lovely and comfortable home well represented by the photos and description
the bed was comfortable & the sheets were soft
Cleanliness:
very nice clean and convenient place
the house was impeccably clean
it felt very clean
very comfortable and clean
cozy comfortable convenient & clean
Host:
thank you for being a great host stephanie
house owner provided us with tons of great recommendations
stephanie is a thoughtful accommodating host and her home is warm inviting and comfortable
and the host stephanie is super great
great house and immecable hosts
Location:
great location for downtown ashland
perfect location to walk to everything
perfect location great hostess
great place and great location
the location is great for walking to downtown jacksonville
Read more reviews

7. Beautiful and luxurious cottage

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.

Stayed at this property?
Jacksonville, Oregon, United States
765 meters (0.5 ft) from Doc Griffin Park
172 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
comfortable bed nice linens and reliable internet
the cottage was perfect for 2 couples plenty of room and an open floor plan
beds: amazingly comfortable bed/linens
hair products lotions toiletries iphone outlets in every room fluffy beautiful robes
the little town of jacksonville has restaurants and great coffee shops/breakfast places a quick walk from the house
Cleanliness:
everything is new and so clean and fresh
as before everything was clean and neat
had a great stay comfortable clean and great communication
the house is clean comfortable and very stylish
very clean fully stocked with everything and more
Host:
she is a great host
jackie was also a great host responded quick and made us feel welcome
jackie is also a wonderful host who is quick to respond to any questions
jackie was an excellent host highly recommended
jackie was a responsive and generous host
Location:
great location just a short walk to everything in town
the location was an easy walk to downtown jacksonville
easy walk to enjoy jacksonville
this spot is an amazing location to walk into the heart of jacksonville
very quiet and safe and super easy walking distance to downtown
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8. Luxurious cottage

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!

Stayed at this property?
Jacksonville, Oregon, United States
765 meters (0.5 ft) from Doc Griffin Park
172 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
comfortable bed nice linens and reliable internet
the cottage was perfect for 2 couples plenty of room and an open floor plan
beds: amazingly comfortable bed/linens
hair products lotions toiletries iphone outlets in every room fluffy beautiful robes
the little town of jacksonville has restaurants and great coffee shops/breakfast places a quick walk from the house
Cleanliness:
everything is new and so clean and fresh
as before everything was clean and neat
had a great stay comfortable clean and great communication
the house is clean comfortable and very stylish
very clean fully stocked with everything and more
Host:
she is a great host
jackie was also a great host responded quick and made us feel welcome
jackie is also a wonderful host who is quick to respond to any questions
jackie was an excellent host highly recommended
jackie was a responsive and generous host
Location:
great location just a short walk to everything in town
the location was an easy walk to downtown jacksonville
easy walk to enjoy jacksonville
this spot is an amazing location to walk into the heart of jacksonville
very quiet and safe and super easy walking distance to downtown
Read more reviews

9. Luxury cottage in Jacksonville's historic core

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.

Stayed at this property?
Jacksonville, Oregon, United States
239 meters (0.2 ft) from Doc Griffin Park
201 reviews   Superhost Wifi Available
ENTIRE HOME 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
the furniture was all very comfortable especially the bed
it’s fashionable and very very comfortable
Cleanliness:
the place was clean and airy very fresh smelling with wonderful comfortable bedding and towels
it’s a clean and aesthetically pleasing home
Host:
jackie always provided a quick response to our many questions and lots of helpful tips
jackie is the best most kind and thoughtful host
jackie is an amazing host her home reveals how she has thoughtfully prepared for your stay
amazing place to stay and great host
it is beautiful she is an exceptional host and we feel pampered staying at her properties
Location:
the location is perfect
within walking distance of shopping and the britt festival
located right downtown we were able to walk to eat and to stores easily
rental was beautiful perfect location gorgeous decor
such a great place and perfect location
Read more reviews

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.

Stayed at this property?
Jacksonville, Oregon, United States
92 meters (302.1 ft) from Doc Griffin Park
168 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
there was no tv (unexpected) but good internet connection/wi-fi
king size bed with heated pad was awesome
the apartment looks exactly like the photos—spacious light and airy and well appointed
the bed is very comfortable the bathroom is spacious with lovely views of the trees from the shower
the living area and kitchen are open and get great light
Cleanliness:
super clean and quite house
extremely clean and light
it was clean and very comfortable
clean functional guest house
ultra clean and extremely comfortable bed
Host:
bruno is a great host
bruno is a great host
bruno is a wonderful host
bruno is a great host he has gone above and beyond our expectations
beautiful town and a most gracious host
Location:
amazing location for the britt walk
great location and cute space
neighborhood was fabulous and location
wonderful apartment located close to the britt
great location near the britt
Read more reviews

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.

Stayed at this property?
Jacksonville, Oregon, United States
85 meters (279.3 ft) from Doc Griffin Park
48 reviews  
Entire house 4 Beds 3 Bedrooms 3 Bathrooms
Top guest reviews
Amenities & Room:
the view from the pool is fantastic
the pool and outdoor grilling/drink mixing/lounging space are better than any hotel
lots of amenities would have loved to be there earlier in the year to use the pool
pool patio and outdoor kitchen was perfect for lounging and cooking all day by the pool
great place with plenty of room for our group
Cleanliness:
the place was beautiful and nice and clean it was a descent trip overall
the cottage and house were sparkling clean and full of decorator accents
clean comfortable period victorian with lots of new things to find and old things to enjoy
their home was squeaky clean and the location can’t be beat
Host:
absolutely gorgeous home with top rate hosts
they are great hosts
julie and jeff are great hosts
couldaccommodate a large party we enjoyed meeting them and they were very helpful
jeff and julie are the absolute best they are warm and friendly hosts who have thought of everything
Location:
the location is very close shops and good restaurants
cute place that is close to everything in jacksonville
the location of the home is perfect short walk to the main strip in jacksonville
beautiful home in a great location
the many near by eating places a bonus thanks again
Read more reviews

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!

Stayed at this property?

449 meters (0.3 ft) from Doc Griffin Park
19 reviews  
Entire apartment 2 Beds 3 Guests

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.

Stayed at this property?

404 meters (0.3 ft) from Doc Griffin Park
45 reviews  
Private room 2 Beds 4 Guests

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.

Stayed at this property?

602 meters (0.4 ft) from Doc Griffin Park
Private room 1 Bed 2 Guests

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.

Stayed at this property?
Jacksonville, Oregon, United States
1.95 km (1.3 mi) from Doc Griffin Park
165 reviews  
Entire house 1 Bed 1 Bedroom 1 Bathroom

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!

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Lilian Tan is a creative storyteller, videographer and producer based in Singapore. She's an explorer at heart, and a writer by choice. She draws her influences from her observations on the beauty...Read more

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