Vacation rentals in Ashland

Book unique homes, vacation rentals, and more on Airbnb

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Stay near Ashland's top sights

Oregon Shakespeare Festival267 locals recommend
Lithia Park198 locals recommend
Ashland Food Co-op91 locals recommend
Brickroom76 locals recommend
Varsity Theatre56 locals recommend
Standing Stone Brewing Company54 locals recommend

House rentals in Ashland

Superhost
A covered deck features wooden flooring and three black wire chairs arranged for seating. A glass door provides access to the interior, complemented by two wall-mounted lanterns and large windows that offer views of the surrounding neighborhood.
Home in Medford
4.91 out of 5 average rating, 107 reviews

Hillcrest Estates

LauriRating, 5 stars2 weeks ago
This is a comfortable home. You can also walk for miles on roads or up on Roxy Ann Peak . I felt very safe here. A great neighborhood.
Guest favorite
A spacious living area features a distinctive curved sofa adorned with dark pillows. A glass coffee table sits on an area rug, enhancing the space. A dining table and chairs are positioned nearby, with a view of the outdoor patio visible through large windows.
Home in Medford
4.92 out of 5 average rating, 13 reviews

Rocky Road Casa, 2 Bedroom

AsadRating, 5 stars1 month ago
Excellent stay. Nice quiet place off the street. Its very private with no one walking near the poperty. Fenced backyard. Well equipped and clean.Just like the pictures. This was my 4th time here for a work trip. Excellent stay each time. I will come back. John and Angela are very considerate, mindful and responsive hosts.
Top guest favorite
A bright living room features large windows that allow abundant natural light, complemented by a comfortable brown sofa and a cozy armchair. Lush green plants add a touch of nature, while a simple coffee table rests atop a textured area rug.
Home in Jacksonville
4.99 out of 5 average rating, 292 reviews

Britt Bungalow in the Heart of Jacksonville

NickRating, 5 stars1 week ago
We had such a wonderful stay at the Britt Bungalow! The home itself is beautiful and serene, with a stunning garden and multiple cozy outdoor seating areas that made it easy to relax and unwind. The location is perfect—right in the heart of Jacksonville, surrounded by great local restaurants, charming shops, walking trails, and even a dog park just minutes away on foot. Our dog loved the stay just as much as we did, especially soaking up the sun in the lovely outdoor space. The host, Tambo, was incredibly hospitable—friendly, responsive, and respectful of all our needs. We loved it so much, we've already booked the bungalow again for our next visit. Highly recommend this gem of a property!
Superhost
A comfortable living area features a gray couch adorned with decorative pillows and a cozy blue chair. A simple white console table is positioned beneath a mounted television, with artwork displayed on the wall. Natural light streams through the window, highlighting the wood-like flooring.
Home in Medford
4.84 out of 5 average rating, 243 reviews

Trailer parking, king bed, great for guests/pets!

PhillipRating, 5 stars1 month ago
nice place, didn't realize it was 2 stories till we got the check in message which is fine. Was nice to sleep didn't hang out much at the house. Was there for an event, pretty much just slept there.
Guest favorite
A neutral-toned living area features a comfortable sofa adorned with decorative pillows, with a coffee table positioned in front. A framed cityscape artwork is displayed on the wall. The open kitchen area includes wooden cabinetry and a dining table with seating for four.
Home in Medford
4.89 out of 5 average rating, 223 reviews

Cheerful new 2 bedroom home in cul de sac Netflix

WendyRating, 5 stars3 weeks ago
This is my second time staying here and will continue to stay when visiting Medford. Everything was perfect in my book. Very comfy bed, full kitchen and everything to make you feel like home. Minutes away from restaurants and shops and location is in a cul de sac so no traffic noise. We had an unfortunate accident happen and Blaine and Steffanie were so kind in letting us check out an hour later. I highly recommend this house, and they also have other rentals as well.
Guest favorite
A cozy living area features a sectional sofa and a leather recliner positioned around a circular coffee table. Natural light floods through the large window, adorned with sheer curtains. A geometric area rug lays over original hardwood floors, enhancing the inviting ambiance.
Home in Central Point
4.91 out of 5 average rating, 137 reviews

Lovely Central Point Home w/EV Charger

JillRating, 5 stars3 weeks ago
I, along with my 12 year old son, and another mom and her son stayed here for our boys baseball tournament. It was SUCH a great, welcoming space to spread out and have a more relaxing experience than staying at a hotel. The boys loved being able to stretch out on the sofa to watch basketball in the evenings on the big TV's , and the bonus space in the garage was such a fun addition. Thanks for a great spot!
Top guest favorite
A spacious living area features a comfortable sectional sofa and a stylish armchair, complemented by a wooden coffee table. Natural light filters through sheer curtains, brightening the space. A woven rug adds texture, while a pendant light provides a warm glow, enhancing the inviting environment.
Home in Medford
5 out of 5 average rating, 14 reviews

Fun and Spunky two bedroom home!

LoriRating, 5 stars3 days ago
Very nicely updated home. Comfortable beds with super soft extra blankets, nice touch. One bedroom is really big and has a walk in closet. Everything was very clean! The upstairs is a very nice added bonus room. We hardly used it but the staircase going up is very sturdy and safe. Bathroom looks new, big soft towels. Kitchen was a little sparse as far as any extras but everything there was all very nice. Good appliances. There is no backyard or outdoor seating. The rooms actually are bigger than they appear in the pictures. The owners of this airbnb did a great job making this home beautiful and comfortable.
Top guest favorite
Home in Ashland
4.98 out of 5 average rating, 128 reviews

Secluded mountain retreat, Ashland 10 m., by PCT

MayaRating, 5 stars1 month ago
Micheline was a fantastic host, super responsive, friendly and made everything easy to access. The property and home were private, beautiful and had the most personable touches I've every seen in an airbnb. We will definitely visit again!

Dog friendly vacation rentals in Ashland

Top guest favorite
A cozy corner of the cabin features a calm dog resting on a soft bed. A small table holds a welcome sign and a plant, while colorful food and water bowls sit nearby. The floor is covered with natural stone tiles, enhancing the rustic ambiance.
Cabin in Jacksonville
4.99 out of 5 average rating, 111 reviews

Private & Cozy Treetop Cabin in Historic J-vile

ArnoldRating, 5 stars2 weeks ago
Had a wonderful stay, Emily was very friendly and attentive with any questions we had. Very private and cozy cabin, also very peaceful.
Top guest favorite
A welcoming nook is created with a decorative corner shelf holding framed art and photographs. A wicker basket contains dog supplies, and a plush dog bed lies beneath a sign reading 'RESERVED FOR THE DOG.' Natural light fills the space from a nearby window.
Home in Medford
4.96 out of 5 average rating, 138 reviews

Clean, comfy, pet friendly & fully stocked

JaneRating, 5 stars2 weeks ago
Amanda's place is great! The attention to details for necessity is amazing. Every room is well stocked and you will have everything you need even down to the feminine products and disposable razors. Our two pups had a great time too. The backyard is perfect them to roam around. Amanda even had a jar of dog treats by the door. The beds were big and conformable. She is also very responsive and flexible on the check out time. Overall, top notch quality!
Guest favorite
Home in Medford
4.95 out of 5 average rating, 125 reviews

1930s Queen Anne Historic Downtown Retreat

EvaRating, 5 stars3 weeks ago
Charming home with plenty of room for a family to be comfortable. Loved all of the recommendations. We felt right at home! We only got to enjoy the place for a quick overnight but it was well appointed with many amenities for a larger group.
Guest favorite
A serene view of a rustic barn house set amidst tall evergreens. The two structures are distinguished by contrasting colors: one an earthy red and the other a muted green. A gravel path leads to the buildings, providing a sense of private tranquility.
Home in Ashland
4.96 out of 5 average rating, 180 reviews

Gorgeous Lakeside HOUSE + Indoor SAUNA!

AdamRating, 5 stars5 months ago
We had such an amazing Thanksgiving stay in the snow. The house and snow-covered outdoors was amazing and was such a magical place for our family to gather. Laurel and Blake were amazing, responsive hosts, especially during a holiday week. Blake quickly fixed a propane heater problem caused by the extreme weather and completely saved our Thanksgiving meal. We were so appreciative of their responsiveness and care, and would love to come back sometime in the future.
Guest favorite
A rustic cabin with a green metal roof sits surrounded by tall trees and lush grass. A stone fire pit is positioned nearby, accompanied by log seating, offering a peaceful outdoor space for gathering.
Cabin in Medford
4.86 out of 5 average rating, 107 reviews

Woodland Cottage near Jacksonville Dog Friendly

JohnRating, 5 stars4 months ago
Candace and RG's place is a real gem. We stayed for an entire month and enjoyed every day of it. The house is fully equipped for extended stays. If you are an outdoorsy type you will fall in love with their gorgeous property which has an extensive network of trails to hike. Candace and RG are wonderful folks and since we are now moving to the area we already have new friends. If you want to spend time in the Rogue Valley but stay out of the urban sprawl you'll be hard pressed to find a better spot. Five big stars!
Guest favorite
A small studio cottage is presented with a light green exterior and a sloped roof. Two red chairs are positioned on a concrete deck, surrounded by planters with greenery. Tall evergreen trees frame the background against a bright blue sky with scattered clouds.
Cabin in Ashland
4.95 out of 5 average rating, 394 reviews

Studio Cottage near downtown Ashland - Queen Bed!

JudeRating, 5 stars4 days ago
I will stay here anytime I'm in Ashland! It's such a fantastic spot. Close enough to drive to anything one needs, but on a private road that is quiet. The property is beautiful, the host amazing, the cottage homey. And what a wonderful time of year to see and smell all the lilacs blooming and have a nice cup of coffee on a wooden bench swing!
Top guest favorite
The cozy chalet is nestled among tall trees, showcasing a wooden exterior with large windows. Lush greenery surrounds the entrance, offering a natural setting. Sunlight filters through the treetops, creating a serene atmosphere in this private retreat.
Guesthouse in Grants Pass
4.96 out of 5 average rating, 191 reviews

Chalet in the Woods

JulieRating, 5 stars1 week ago
Awesome cabin in the woods! It felt so private and secluded, even though we were 5 minutes from town. Great location and had everything we needed. Lots of wildlife, turkey's gobbling every morning by 5am. Deer walked through the yard every morning. Hot tub was perfect. Angela gave great local recommendations!
Top guest favorite
The cozy cabin is surrounded by vibrant autumn foliage, with a wooden porch that offers seating. A blend of trees provides privacy, and a garden pathway leads toward the entrance, showcasing natural beauty with seasonal colors.
Guesthouse in Medford
4.98 out of 5 average rating, 126 reviews

Creekside Cabin

BrettaRating, 5 stars4 months ago
Cozy cabin just outside of Medford. Cute town. The cabin was decorated for Christmas. Our dogs loved exploring the property and playing with Monte the golden that lives there. The cabin was comfy, super clean and all the little personal touches made it very relaxing.

Dog friendly homes in Ashland

Top guest favorite
A comfortably arranged living area is highlighted by a brown leather sofa and a round coffee table atop a plush area rug. Natural light filters through sheer curtains, illuminating the space and a decorative fireplace contributes to the serene environment.
Home in Medford
4.98 out of 5 average rating, 105 reviews

Charming One

SallyRating, 5 stars2 weeks ago
Such a unique space. Cozy and homey, the original finishes were beautifully maintained and everything worked, the furniture well appointed and the beds were perfect. Very comfortable. The personal touches that Dahely added made the stay so much more enjoyable. Also, shower pressure was amazing. :)
Guest favorite
A backyard playground features a wooden structure with a slide and climbing area, surrounded by greenery. A swing set with multiple swings stands alongside. Children can be seen playing, while a dog watches nearby. The space is bathed in natural sunlight, enhancing the inviting atmosphere.
Home in Ashland
4.9 out of 5 average rating, 60 reviews

Pet Friendly w/ hot tub by town!

ScottRating, 5 stars1 week ago
Wonderful home - the photos don't do it justice. Plenty of space, including plenty of negative space; nicely decorated - very pleasant on the eyes. Plenty of plates, utensils, etc. King bed was nicely firm with sometime of soft/pillow top. Plenty of pillows, indoor towels, towels for hot tub. Large backyard with plenty of seating, great hot tub, nice outdoor table under shade cover for meals. Michael lived next door and was very friendly and welcoming. About a 10 minute walk to the heart of town/Shakespeare Festival.
Guest favorite
Home in Eagle Point
5 out of 5 average rating, 17 reviews

Eagle Point Getaway - Horse & Pet friendly

Chris And TamiRating, 5 stars2 weeks ago
We LOVED this place! The views from the house are gorgeous, and the house itself is clean and comfortable. The house is well supplied with everything guests might need (plenty of pots and pans, spices, additional towels and linens, laundry soap, etc.), as well as "extras," such as DVDs, games, and wood for the wood stove. We were delighted with the wild turkeys, deer, and beautiful flowers on the property, and we enjoyed seeing and hearing the cows in the distance. The incredible beauty and peacefulness of this home is wonderful therapy for the soul! Dorothy was a responsive and gracious host, and we hope to stay at her place again. This home is a 10/10!
Top guest favorite
Home in Medford
4.99 out of 5 average rating, 105 reviews

Chic 4 bed/2 bath house with large yard

SandeRating, 5 stars1 month ago
The communication was great. That's really important if you're unsure about things. Kitchen was stocked amazingly well with things I needed for baking & cooking. Fenced yard & patio was enjoyed by everyone and there was plenty of room for 4 adult, 2 children & 2 small dogs. We will enjoy our memories made here in Medford Oregon!
Top guest favorite
A patio area is visible, featuring a comfortable seating arrangement with outdoor cushions. Green vines climb the posts of a pergola, while a propane grill is seen in the background. A well-maintained lawn and a storage shed complete the outdoor space.
Home in Medford
4.92 out of 5 average rating, 201 reviews

🌟30 DAY-25%🌟PET FRIENDLY🌟PRIVATE🌟FENCED YARD🌟W/D🌟

EmilyRating, 5 stars2 months ago
I'm a repeat to King of Queens. Suzanne's place is perfect for my extended stays for work. My dog loves the fenced back yard. Suzanne is an amazing host! I always hope her place is available when I need to go to Medford! Highly recommend!
Guest favorite
The entrance features a welcoming front porch adorned with a decorative door surrounded by colorful plants and flowers. A stone pathway leads to the door, flanked by neatly trimmed greenery. A bench offers a cozy spot to enjoy the outdoor scenery.
Home in Medford
4.83 out of 5 average rating, 24 reviews

Luxury Home in East Medford

ValerieRating, 5 stars2 months ago
Joel was very helpful. We needed a quick place to move for our home remodel which of course grew. The house is very nice and convenient. Bathrooms and towels very clean. The property was well cared for. The microwave is hard to use as its screen is very dark. We had to guess. This property is excellent.
Guest favorite
A charming craftsman-style home is framed by lush green landscaping and white flowering bushes. The inviting front porch features a wide staircase leading to the entrance, with a combination of windows and gables adorning the roofline. Natural light bathes the exterior in a warm glow.
Home in Medford
4.92 out of 5 average rating, 153 reviews

Historic Upstairs Apartment

LukeRating, 5 stars4 days ago
Clean, close to downtown, cool unique property. Would stay again.
Superhost
An outdoor deck area features a shaded seating arrangement and a hot tub, surrounded by lush greenery. The deck connects to the house, which has a light-colored exterior and ample large windows. The space is designed for relaxation and social gatherings.
Home in Gold Hill
4.87 out of 5 average rating, 162 reviews

Drift Away

HannahRating, 5 stars1 week ago
My best friend lives out of state so we rented this beautiful home to meet in the middle and relax with our two small pugs and also enjoy some wine tasting. Once you walk in and see the gorgeous landscape you realize you’re in a special place in nature. If you do bring a pup I recommend bringing a little dog gate and an out door blanket and enjoying the rocking chairs on the balcony deck stress free of runaways, it was the perfect way to spend a morning/sunset with a beautiful view of the rogue river. It was also great being a quick 4 minute walk to a local market with snacks and beverages. Added bonus - even the beds in the non primary bedroom are super comfortable and queen sized bunk beds with quality linens and comforters. I look forward to renting again!

Quick stats about vacation rentals in Ashland

  • Total rentals

    340 properties

  • Total number of reviews

    22K reviews

  • Family-friendly rentals

    120 properties are a good fit for families

  • Pet-friendly rentals

    130 properties allow pets

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Ashland?

    Yes! Work meets play with ease at over 170 vacation rentals in Ashland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in cottage rentals in Ashland?

    Experience the best of Ashland with our cottage rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Ashland?

    Four-legged friends are welcome in Ashland. Choose from more than 130 vacation rentals for guests traveling with pets.

  • Are there Ashland vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Ashland, available on Airbnb. Make a splash and soak up the sun in style!

  • Do guesthouse rentals in Ashland have air conditioning?

    Absolutely! We offer over 20 guesthouse rentals with air conditioning in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Ashland have self check-in?

    Absolutely! We offer over 10 cottage rentals with self check-in in Ashland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cottage Rentals in Ashland?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Ashland?

    Ashland has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland