
Vacation rentals in Ashland
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Top-rated vacation rentals in Ashland
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Popular amenities for Ashland vacation rentals
Dog friendly vacation rentals in Ashland

Private & Cozy Treetop Cabin in Historic J-vile
I just LOVED it here. Everything about it. It's a beautiful outdoor setting and I felt surrounded by the mountains and trees. So peaceful. Jacksonville is just five minutes down the road and there is so much to do in the area if you are a nature lover. My dogs loved the outdoor patio area, and there are leads to attach them so they can explore without getting out of sight. The inside of the cottage is beautiful, too. Well-stocked and very cozy. I could have stayed for many more days. What a treat.

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

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!

Sand Creek Cottage
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,

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.
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.

Washington Blvd Historic District Cottage
Great spot!!!

Heron House King Bed Views
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.

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!
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.

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

Charming One
Our stay at Dahely's home was truly delightful. The home itself is remarkably spacious, with a comfortable and flowing layout that made it easy to relax and unwind. The neighborhood is so quiet and peaceful – we especially enjoyed watching the wild turkeys stroll by in the morning! It's a lovely setting. We also loved the pretty living room, which was just perfect for enjoying a cup of coffee. It's such a welcoming and serene space.

Downtown Cottage with King bed
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.

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
The house was so clean and beautiful! one of the best Airbnb experiences I've ever had. Stefanie responded quickly whenever I needed anything and the house was so cozy and spotless clean! would 10/10 recommend staying here!

🌟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.

Historic Upstairs Apartment
I had a great stay at this Airbnb. It was exactly as listed: clean, cozy, and perfect for a solo trip. The space was thoughtfully set up, the bed was comfortable, and the Wi-Fi worked perfectly for both work and streaming. The location was convenient and safe, and the host was friendly and responsive throughout my stay. I would definitely book again next time I’m in the area.

Plymale Cottage Bed & Biscotti - 2BR, Kitchen, AC
Absolutely adorable! I’ve spent my last two birthdays here and plan to continue in doing so. Loni makes check in and out a breeze. She’s incredibly thoughtful and pays attention to detail. The location is absolutely spot on- no need for driving as everything is walkable. If you choose to stay consider booking a wine hopper tour with Robbie, she picks you up right across the street from Loni’s place. While being located near downtown this Airbnb is still on a quiet street and provides a very intimate and cozy experience. Thank you for another wonderful visit!
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.
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