House holiday rentals in Ashland

Find and book unique houses on Airbnb

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Popular amenities for Ashland house rentals

House rentals with a pool

Top Guest favourite
Home in Medford
5 out of 5 average rating, 15 reviews

Cherry Lane, Crystal Skies

EddieRating, 5 stars5 days ago
The home was clean, pool/spa was an added bonus
Top Guest favourite
Home in Grants Pass
4.97 out of 5 average rating, 32 reviews

Pool/Hot Tub/75 inch TV/1000mbps/Brand New

RachelRating, 5 stars2 months ago
Enjoyed our stay. The house was nice, very clean, and the beds were comfortable.
Superhost
Home in Central Point
5 out of 5 average rating, 4 reviews

Rellik Winery - The Rellik House

AprilRating, 5 stars9 months ago
This is such a beautiful home. The setting in the winery is an added bonus. Peaceful, relaxing and refreshing. We rented the entire house and it worked out well. There is the common room but also we had our separate bedrooms to retreat to whenever we wanted. The host was extremely helpful, kind, and responsive. The staff at the winery were extremely friendly as well. The pool and hot tub were clean and easy to use. There wasn’t one bad thing about this place. It is set up perfectly for a family to enjoy a nice home. Even without renting the entire house you still feel like you’re the only one there. Such an enjoyable experience. Will definitely stay here time and time again. Thank you to Valisatie for being such a wonderful host. The house and property are beautiful.
Top Guest favourite
Home in Grants Pass
5 out of 5 average rating, 66 reviews

The Cherry Cottage with built in pool & Hot Tub

NatashaRating, 5 stars1 month ago
Darline’s house is beautiful! We came for fishing but our fishing trip was canceled so we just ended up hanging out around Grants Pass and at this wonderful house. It is well stocked and Darline has thought of everything. There’s extra towels, even sanitized swim wear incase you forgot some for the hot tub or the pool! We were so pleased with our stay!
Guest favourite
Home in Jacksonville
4.89 out of 5 average rating, 90 reviews

Jacksonville Mountain Retreat!

TeresaRating, 5 stars1 month ago
Diana‘s place was immaculate. More beautiful than the photos surrounded by nature. The hot tub was awesome since it rained for our stay. Plenty of space for an entire family. I want to come back and have my family in Oregon stay with us there too. We really felt like we were at a mountain retreat. With the small town of Jacksonville just a few miles away. We had a really fantastic time.
Guest favourite
Home in Medford
4.96 out of 5 average rating, 23 reviews

Capital House - Private getaway with POOL!

SarahRating, 5 stars6 months ago
Perfect spot for our little family to stay for the weekend! Love the open kitchen into living room. Super comfortable master king bed!
Guest favourite
Home in Ashland
4.9 out of 5 average rating, 42 reviews

Indulgent Retreat: Pool, Hot Tub, Sauna

ChelseaRating, 5 stars3 months ago
Beautiful, clean, spacious home. We enjoyed our stay! Sylvie was a great a host! There are some neighbors windows overlooking the yard, so if you are looking for 100% privacy while using the beautiful yard amenities, you may not consider it suitable, but that did not bother us and we had a relaxing time in the hot tub. Small details, like plenty of hot water in all sinks and showers, and a fully equipped kitchen, make this ideal for large families or up to ten guests comfortably. Finally the yard is fully fenced, making it easy to let the dog into the back yard without worrying he would escape. We plan to stay here again!
Guest favourite
Home in Medford
4.83 out of 5 average rating, 24 reviews

Luxury Home in East Medford

ValerieRating, 5 stars3 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.

Weekly house rentals

Top Guest favourite
Home in Medford
4.98 out of 5 average rating, 107 reviews

Charming One

MadisonRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Jacksonville
5 out of 5 average rating, 5 reviews

Upstairs 4 Bedroom Applegate Valley

ShirleyRating, 5 stars4 months ago
Staying at Tiffany's airbnb was lovely. My sister, her family and my mother, stayed there over the Christmas holiday as I did not have enough room in my home to host them, they found it lovely, it was such a nice break from each other to go to our separate homes. Then come together. For meals and outings.
Top Guest favourite
Home in Medford
4.96 out of 5 average rating, 91 reviews

Brookdale Meadows Farmhouse Cutie

VuRating, 5 stars2 weeks ago
We highly recommend this house, especially for an extended stay in Medford and the surrounding areas in the Rogue Valley. We stayed for 3 weeks, and it was an extremely comfortable home away from home. We were there with a young baby and felt safe and comfortable. Most importantly, the house was spotless when we arrived. It is fully stocked with comfortable furniture, kitchen needs and other amenities, and it’s in a nice, quiet neighborhood perfect for walks or relaxing in the backyard. While we had absolutely no issues during the stay, the hosts were extremely responsive before and during the stay; when we noticed we were running low on trash bags, they replied in under 5 minutes that an Amazon shipment was en route. It’s also a short drive to Ashland, Jacksonville, and other areas. We will absolutely plan to stay here on any future visits to the area.
Guest favourite
Home in Medford
4.88 out of 5 average rating, 8 reviews

30+day Unit B*King*yard 4 dog*4min Prov 7min Rogue

AmyRating, 5 stars4 months ago
This property was perfect for a long-term stay. The area was safe, the property well maintained and clean, and Jill was a terrific host.
Guest favourite
Home in Medford
4.93 out of 5 average rating, 14 reviews

Rocky Road Casa, 2 Bedroom

UlyssesRating, 5 stars1 week ago
I recommend John's place! It's got it's own backyard, it's a very quite location, easy walking distance to Safeway, and easy driving distance to Trader Joe's. John is easy to communicate with and responsive to messages. I'd stay there again!
Top Guest favourite
Home in Jacksonville
4.99 out of 5 average rating, 293 reviews

Britt Bungalow in the Heart of Jacksonville

CassieRating, 5 stars2 weeks ago
The Britt bungalow is absolutely adorable, it looks like it’s right out of a magazine. Tammy was a wonderful host and stayed in communication with me in case I needed anything. We didn’t see a show at the Britt this time but if you are this would be the perfect spot to do so. We can’t wait to stay in Jacksonville again and when we do we know exactly where we are staying! This spot is walking distance to coffee shops, restaurants, wine lounges , the Britt and live music.
Superhost
Home in Medford
4.74 out of 5 average rating, 90 reviews

Eva G's get away

AddieRating, 5 stars3 weeks ago
I enjoyed the house it was very roomy and cozy. I love how secluded it felt but how close to everything it was. There was plenty of parking and it was spacious. It was like camping in a cabin within 5 minutes of town.
Guest favourite
Home in Jacksonville
4.87 out of 5 average rating, 275 reviews

Plymale Cottage Bed & Biscotti - 2BR, Kitchen, AC

KayleeRating, 5 stars1 month ago
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!

Private house rentals

Guest favourite
Home in Talent
4.95 out of 5 average rating, 19 reviews

Beautiful 3-bedroom Family House

JeremyRating, 5 stars4 months ago
Great place, clean, quiet, and comfortable. Perfectly placed between Medford and Ashland. Walking distance to cute little restaurants and the Cider place is cool. Really enjoyed our stay
Top Guest favourite
Home in Grants Pass
5 out of 5 average rating, 59 reviews

Brand New/Self Check-In/Smart TV/Full Kitchen

LorieRating, 5 stars2 weeks ago
This was the second time I have stayed at Ian’s AirBnB. First time, there were 5 of us. Second time, only 2. It is in a very nice, quiet location, a few minutes drive to town, grocery shopping, etc. House is very clean, with very comfortable beds (very important to us), very complete kitchen amenities (very important). We will definitely stay here when we visit Grants Pass again & be fortunate Ian’s AirBnB is available.
Superhost
Home in Phoenix
4.79 out of 5 average rating, 464 reviews

Craftsman cottage built in 2019

BobRating, 5 stars2 weeks ago
We were a family of 4 traveling with pets on a quick weekend trip. Gabriel was very quick to respond to the booking and questions we had. Nice quiet neighborhood and very good directions to place We will definitely book with Gabriel again!!!!!!!
Superhost
Home in Medford
4.74 out of 5 average rating, 66 reviews

Newly renovated house with King beds

BretRating, 5 stars1 month ago
Great house and very clean. We needed a stopover on our way from SF to UW. Great halfway point to relax and get some rest. Would recommend it to others and will definitely be back. Thank you for hosting.
Superhost
Home in Ashland
4.86 out of 5 average rating, 97 reviews

Cute 2 bdr house near downtown (pet friendly)

DianaRating, 5 stars2 weeks ago
A few short blocks from the center of town and all the activities of OSF. But quiet and off the main Street. Comfy linens and good mattresses and pillows. Comfortable sofas and living room. Spices for cooking and good collection of pots and pans. Nice to have washer & dryer Excellent communicator Highly recommend
Guest favourite
Home in Medford
4.97 out of 5 average rating, 59 reviews

Lotus House-Comfy, Walk to Park, Centrally Located

Rating, 5 stars3 weeks ago
This was a very pleasant stay. This is a place that you feel like at home. We arrived at around 23:00 the first day and Tina kept the lights on for us, looked like the house was welcoming us. We cooked, washed clothes, even played board games. Supply in the house was sufficient and Tina responded quickly on questions, so very convenient. I love this place and definitely will choose again next time.
Guest favourite
Home in Ashland
4.91 out of 5 average rating, 127 reviews

The Madrone House, mountain views.

PattyRating, 5 stars4 months ago
This was the perfect location for my California & Oregon family to celebrate Christmas. There were toys for the toddlers and even a small Christmas tree. The bedrooms were cozy and warm. And Kitchen was well supplied. 30 minute drive to the snow recreation area. Their dog Austie was a family favorite. Thanks for making our Christmas merry!
Guest favourite
Home in Medford
4.88 out of 5 average rating, 24 reviews

Clean, Cozy Family Style House. Near Hospital.

BrendaRating, 5 stars5 months ago
Very helpful owner, always reply quickly and being supportive. The location is opposite hospital with friendly neighbors. The house is very nice and welcome, feel like home.

Quick stats about house rentals in Ashland

  • Total rentals

    110 properties

  • Total number of reviews

    6.3K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    100 properties include access to Wi-Fi

Destinations to explore

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  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland
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