Guesthouse holiday rentals in Ashland

Great location, close to wineries and Jacksonville.

This really is a dream cottage! It’s right on the Rogue River. My dog and I woke up every morning and went down to the river, and it was never the same twice. Incredible birding, and even saw some river otters! Sam’s sculpture adds a lot of fun surprises to the property- you never know what’s going to appear. The bed was very comfortable, and the kitchen has everything you need to feel right at home. Sam and Paula were so kind and welcoming. Can’t recommend it enough!

This place was perfect for my bigger size family and our pet! Very comfortable and had beautiful views! We definitely recommend this home and would definitely go back!!

We had a wonderful stay at this Airbnb. It is a cozy and inviting space! The beds were comfortable, and everything was very clean. The hosts have considered nearly every detail you might need in the kitchen, bathroom, and bedrooms. They provide a link with useful information, which was helpful. We truly felt at home. The sound of the river at night was priceless. The place offered great privacy, allowing for a genuinely relaxing experience. Thank you for making everything a breeze.

Very beautiful area. Had lots of fun in the awesome pool. My daughter was amazed at all the wildlife in the area. The room was very charming and had a rustic feel to it, but had all the modern amenities. All in all we had a great time and couldn't ask for a better location or host. Teresa was very friendly and helpful

Had an excellent stay here. Would absolutely stay again. Space was just right. Excellent hosts!

Had a great stay here! Jim was a very welcoming host who accommodated a last minute stay. The place was very comfortable, and Jim gave very clear instructions that I appreciated

Julie's cottage fit our needs perfectly. Casita Sirena is charming - comfortable, bright, colorful, and decorated with whimsical mermaid-themed artwork. We were a 15 minute walk from the theaters, town center, and Lithia Park. When we weren't walking in the park or attending plays (GREAT selection of plays this spring!), we enjoyed reading on the front porch. There was a binder in the cottage with restaurant and activity recommendations, and very clear instructions for how to use the heat and A/C and what to do when checking out. Julie was great at communicating with us, and responded promptly to messages. Our stay was wonderful!

We would definitely stay at this Airbnb again! The property is so quaint and peaceful. The location is very close to Ashland and is a must stay.

Staying at Ivan's this past week was exactly what my little family and I needed! We live in Grants Pass but, we love to do little getaways/staycation. His studio and propert were beautiful, quiet and, peaceful. Loved watching the chickens and babies. Definitely recommend for a staycation or if you're from out of town this is an amazing little Airbnb.

we had a great stay at peach pit in it was so cute and you can tell Rebecca really paid attention to the details. definitely better than staying in a hotel!

As advertised! Hanna’s house was in a terrific location (VERY walkable to all the things, but tucked away enough that I heard no noise at night), and every thoughtful detail accompanied this Airbnb. Loved it.

The cottage and the property are idyllic and the owners (Nicole and Fernando) are wonderful. They are friendly, accessible, responsive and just about everything you'd want or expect from the host. All of the amenities were as shown and advertised. The only "negatives" were (1) the fact that this a country property means lots of flying and crawling insects, and (2) the property is in a remote country setting. If you're looking for a quiet, relaxing place to unwind, this spot is a gem. If you're interested in a convenient place to stay while enjoying social experiences (dining, theater, shopping, etc.), be prepared to drive a bit.

I cannot say enough wonderful things about this place. It’s enchantingly serene, the property is immense with walking trails everywhere, the on-site hosts, Virginia and Al, are incredibly welcoming and exceedingly kind. They are some of the sweetest people I have ever met. We were greeted by them on arrival with some wine and chocolate for the holiday. We enjoyed the stars every night we were there and the space itself is absolutely beautiful. It is the definition of “home away from home” and I hope I get to visit again someday!

Great stay with a beautiful private pool and hot tub. Finishes inside were top notch - gave me ideas for my own kitchen. Potential guests should know the bedroom is upstairs while the bathroom is on the main floor down a flight of wooden stairs - something to keep in mind if you have balance issues in the middle of the night. A lovely place for a getaway in Medford.

Susan is an experienced, friendly, and thoughtful host. The Silver Frog studio is well-designed for a couple and has a lovely outdoor shaded patio and garden area for relaxing with morning coffee provided in unit. Location is easily walkable to OSF theaters, Lithia Park, restaurants, everything downtown and the historic Railroad District! No need to have a car, but if you do, off-street parking is provided on-site. Silver Frog Studio is a rare find, a sweet spot for a getaway, with so much to do close-by!

Bryanna's place is spotless, very beautifully decorated and spacious. There were all the amenities that are shown in the photos. She was friendly, flexible, and responsive about checkin. Very minor, but the bed pillows were extremely flat and the twin beds not the most comfortable. All in all a great stay, if a bit pricey for the area.

This little barn is fixed up so nice. The bed was very comfortable and the place was quiet and secure. I loved all the extra touches..fresh eggs! It is more beautiful than the photos and super clean.

This is our second time staying at Angelica's cozy home, and I know it won't be our last. We have a soccer tournament every year in Rouge Valley and Angelica's house is the perfect location for all the games, and is the perfect spot for relaxation between the busy tournament schedule. The house is cozy and has everything you need. Angelica is a great host. She is responsive and we look forward to future stays.

This was our second stay at Natalie’s cottage and it was as wonderful as the first stay. The cottage is lovely, very private and right in town. We enjoyed every minute of our stay and look forward to our next visit.

This cute place is private and welcoming! The hot tub is an added plus! So close to Jacksonville, gorgeous area! Highly recommend!

This place was wonderful!! Felt right at home the moment we checked in. So happy they are pet friendly! Even has a private yard for the animals. I was very thankful for her letting me check in an hour early too. The place was clean and had everything we needed. Thank you so much!

What a great stay. The location was fantastic, and a very easy walk to the Shakespeare festival, and tons of great restaurants. Safeway is also only two blocks away. The place was immaculate. The bed was super comfy and the kitchen well outfitted. I recommend it!

Super comfy and cute. Nice stay for overnight rest. Also Shannon was a great host, and very accommodating to my family. 🤍 we'd love to stay again.