
Vacation rentals in Ashland
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Top-rated vacation rentals in Ashland
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Ashland vacation rentals
House rentals in Ashland

Hillcrest Estates
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.

Britt Bungalow in the Heart of Jacksonville
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!

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

Cheerful new 2 bedroom home in cul de sac Netflix
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.

Lovely Central Point Home w/EV Charger
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!

Fun and Spunky two bedroom home!
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.

Secluded mountain retreat, Ashland 10 m., by PCT
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.

777 House
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

Private & Cozy Treetop Cabin in Historic J-vile
Had a wonderful stay, Emily was very friendly and attentive with any questions we had. Very private and cozy cabin, also very peaceful.

Clean, comfy, pet friendly & fully stocked
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!

Gorgeous Lakeside HOUSE + Indoor SAUNA!
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.

Woodland Cottage near Jacksonville Dog Friendly
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!

Studio Cottage near downtown Ashland - Queen Bed!
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.

Ideal & quiet location, 3BR+office, perfectly cozy
Great place to stay we felt it was comfortable, clean, and a safe area.

Creekside Cabin
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.

Starthistle Cottage in Applegate wine country
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

Charming One
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. :)

Pet Friendly w/ hot tub by town!
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.

Chic 4 bed/2 bath house with large yard
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!

1930s Queen Anne Historic Downtown Retreat
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.

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

Luxury Home in East Medford
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.

Sweet Valley Home with fully fenced backyard
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.

Historic Upstairs Apartment
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.
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