
Vacation rentals in Ashland
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Top-rated vacation rentals in Ashland
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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.

Rocky Road Casa, 2 Bedroom
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.

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!
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 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!

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.

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!
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!

Chalet in the Woods
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!

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.
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.

Eagle Point Getaway - Horse & Pet friendly
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!

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!

🌟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
Clean, close to downtown, cool unique property. Would stay again.

Drift Away
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.
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