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

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.
Guest favorite
An outdoor patio area features a stone table surrounded by four metal chairs. A charcoal grill is positioned beside the patio, with a small blue basket nearby. A shed sits in the background, complemented by a lush green lawn and trees providing a natural setting.
Home in Grants Pass
4.93 out of 5 average rating, 150 reviews

1912 Home w/Modern Amen-spacious-cozy-dog friendly

TammyRating, 5 stars1 month ago
We enjoyed our stay. Often times AIRBNB’s are furnished with cheap uncomfortable furniture and kitchenware is awful and linens are rough. Vickie however clearly furnished her home in a way that is comfortable for her and therefore comfortable for us. I really appreciated the electric couch recliners having had two knee replacements in the past couple years. It’s often hard to get comfortable but I was very comfortable. She provided so many sweet touches and was really responsive to us as well as very quick to resolve a very minor thing that honestly didn’t need to be remedied but she did and then some. I highly recommend this home and hope to come back.
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
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 stars4 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!
Top guest favorite
A cozy living area features a blue sofa adorned with colorful pillows, situated next to a wooden coffee table. A wood stove provides warmth, complemented by large windows draped in floral curtains, allowing natural light to fill the space. A staircase spirals elegantly in the background.
Guesthouse in Grants Pass
4.98 out of 5 average rating, 239 reviews

Sand Creek Cottage

RussellRating, 5 stars2 weeks ago
Quaint, Quirky and Quiet. Quant - peaceful little cottage on a wooded lot away from town Quirky - the spiral starcase had its own unique charm Quiet - away from the city, all I could hear was the nearby creek, bursts of frogs at night and the wind in the trees. Just the kind of stay I look for,
Guest favorite
The exterior of the home is presented with a well-kept lawn and landscaped garden beds. A large driveway leads to a two-car garage. A vibrant tree provides a splash of color against the neutral siding of the house, while sunlight filters through the leaves.
Home in Central Point
4.93 out of 5 average rating, 163 reviews

Ideal & quiet location, 3BR+office, perfectly cozy

CodyRating, 5 stars3 weeks ago
Great place to stay we felt it was comfortable, clean, and a safe area.
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.

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 stars1 week 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
The cottage exterior is framed by mature trees and shrubs, showcasing a comfortable front porch. A well-maintained lawn stretches across the front, providing a welcoming appearance. The brick chimney adds a classic touch to the charming building, set against a clear blue sky.
Home in Grants Pass
4.88 out of 5 average rating, 104 reviews

Washington Blvd Historic District Cottage

ForrestRating, 5 stars2 weeks ago
Great spot!!!
Top guest favorite
Home in Grants Pass
4.95 out of 5 average rating, 173 reviews

Heron House King Bed Views

LindseyRating, 5 stars1 week ago
We had an event in Grants Pass and our family enjoyed staying a week at Jennifer's place. Everything was as it is described in the listing. Check in and out was easy. It is quiet and peaceful. We felt like we had enough room for everyone and slept well! Jennifer was quick to respond to any questions we had and provided us with clear instructions. Next event we have we will book again.
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, 242 reviews

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

PhillipRating, 5 stars4 weeks 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 stars1 day 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, 127 reviews

Secluded mountain retreat, Ashland 10 m., by PCT

AlyssaRating, 5 stars2 months ago
We had the most amazing stay at this beautiful snowy forest home! The setting was absolutely magical, with snow gently falling outside and a peaceful, serene atmosphere. The home itself was cozy, warm, and inviting, with thoughtful and eclectic touches that made it feel like a true retreat. We loved the spacious living areas, the stunning views of the forest, and the well-equipped kitchen that made it easy to enjoy our time indoors. The location was perfect for exploring nearby trails, and we couldn’t have asked for a more relaxing escape. Highly recommend this gem for anyone looking for a peaceful getaway. Our host, Mich, and her pup Kellen were an extra treat to help everything feel like home away from home.

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. :)
Top guest favorite
A bright bedroom showcases a spacious bed dressed in neutral linens, accented by decorative pillows. A comfortable chair is positioned near the window, and a colorful area rug enhances the cozy ambiance, complementing the light-colored walls and natural light entering the room.
Home in Grants Pass
5 out of 5 average rating, 11 reviews

Downtown Cottage with King bed

RyanRating, 5 stars1 month ago
Had a great stay here. Really nice beds, washer and drier work great, and WiFi is fast. Roku TVs so you can watch your favorite streaming services. Cozy little house.
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!
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.
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.
Superhost
A peaceful backyard is enclosed by greenery and wooden fencing, providing privacy. Lush grass covers the ground, complemented by flower beds along the perimeter. Sunlight filters through the trees, creating a serene outdoor space ideal for relaxation or play.
Home in Grants Pass
4.85 out of 5 average rating, 13 reviews

Sweet Valley Home with fully fenced backyard

RobertRating, 5 stars4 months ago
We had a great weekend! The house is beautiful, and cozy, and nestled in a very nice, quiet neighborhood. Very close to some good restaurants and stores. The host was very helpful and responsive, and even provided a list of activities to do in town. 5/5, will definitely stay again.
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 stars2 days ago
Clean, close to downtown, cool unique property. Would stay 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