Vacation rentals in Ashland

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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 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.
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, 242 reviews

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

PhillipRating, 5 stars3 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 stars2 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, 136 reviews

Lovely Central Point Home w/EV Charger

JillRating, 5 stars2 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, 13 reviews

Fun and Spunky two bedroom home!

AlexRating, 5 stars1 week ago
Clean, cozy and well equipped kitchen and amenities. Furniture and beds are quite comfortable and there is plenty of room inside and out with a beautiful tree in front of the house. Quiet and serene neighborhood, close to town center and shopping. Beds are quite comfortable and even though we did not use the loft, it is quite nice and well organized for entertainment and watching a movie or hanging out.
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.
Guest favorite
The entrance features a sleek, modern front door flanked by two small windows. A large potted plant adds a touch of greenery, while the concrete steps lead to a welcoming entryway. The exterior showcases a blend of wood and metal materials, creating a stylish façade.
Home in Grants Pass
4.94 out of 5 average rating, 242 reviews

777 House

SaraRating, 5 stars1 week ago
Beautiful home, very quiet and peaceful. We had all the essentials for our stay. Easy to get to and close to shopping areas. We felt very at home, and would stay here again if we are in the area 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 stars1 week 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, 137 reviews

Clean, comfy, pet friendly & fully stocked

JaneRating, 5 stars1 week 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!
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, 389 reviews

Studio Cottage near downtown Ashland - Queen Bed!

AllenRating, 5 stars3 days ago
This is the third time we’ve stayed here and I can’t imagine staying anywhere else. The hospitality is superior, from welcoming treats to extra amenities for our dogs. The surroundings are quiet and beautiful. And it doesn’t take long to drive to the theaters. A great place to relax.
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.
Top guest favorite
The cottage exterior is seen from the pathway, featuring a fenced yard for privacy. A covered porch is visible, as well as a concrete walkway leading to the entrance. Lush greenery surrounds the home, enhancing the rural setting.
Guesthouse in Jacksonville
4.98 out of 5 average rating, 178 reviews

Starthistle Cottage in Applegate wine country

KelliRating, 5 stars4 weeks ago
What a wonderful and peaceful place to get away. Linda is a great host, with excellent communication and the welcome book is very informative. It’s such a beautiful setting, the home was just as described and it was very cozy and comfortable. You’re close to so many places, Jacksonville, Central Point, Medford etc. We love that we could bring our pup and that there’s a fenced yard. We really enjoyed our stay and will definitely be back. Thank you Linda!

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 stars1 week 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 stars3 days 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.
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, 124 reviews

1930s Queen Anne Historic Downtown Retreat

EvaRating, 5 stars2 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
4.91 out of 5 average rating, 151 reviews

Historic Upstairs Apartment

HeatherRating, 5 stars2 weeks ago
This location is truly a gem! I needed a place to stay for my daughter's late-night flight arrival in Medford and this location was not only very close to the airport but newly remodeled to reflect the historical beauty of the home with artful, intentional, comforting touches. The art was lovely, the bed was comfortable, and all of the welcoming touches made us feel immediately at home. I especially loved the antique furniture and pleasing details of the charming home. The ability to make hot tea and simple meals was also a bonus! Would definitely 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 private suite rentals in Ashland have air conditioning?

    Absolutely! We offer over 30 private suite 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 House Rentals in Ashland?

    Enhance your stay in our House Rentals with the most popular amenities: over 100 homes with air conditioning, over 30 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

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