House holiday rentals in Ashland

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Popular amenities for Ashland house rentals

House rentals with a pool

Guest favourite
Home in Central Point
5 out of 5 average rating, 12 reviews

Rellik Wine Suite near Jacksonville Hot Tub/Pool

LakeiaRating, 5 stars6 months ago
We stayed here for Thanksgiving and it surely was a place to be grateful for. I love that this place is dog friendly and allows for guests. We were able to invite my sister (who we were there visiting) over to show of the beautiful grounds. There were doggy bag stations all over, which is always so appreciated! The room was very cozy and kept at a comfortable temperature, which was much appreciated during this cold month. I do recommend to any guests to make sure you either wipe your shoes off really well or just take them off inside because the gravel really sticks to your shoes and tracks inside easily. we learned this after it was too late. The property was absolutely breathtaking! We loved every second of it here and we look forward to coming back in the future to try the winery and restaurant.
Top Guest favourite
Home in Medford
5 out of 5 average rating, 22 reviews

Cherry Lane, Crystal Skies

CherylRating, 5 stars2 days ago
The house is lovely and Amanda was very responsive!
Top Guest favourite
Home in Medford
4.96 out of 5 average rating, 25 reviews

Capital House - Private getaway with POOL!

DanRating, 5 stars3 weeks ago
Our family loved staying at Dianne's place! It was even better than the pictures let on, and we hope to stay again in the future. It was a very private home/yard in a quiet and peaceful neighborhood that was great for morning and evening walks. The location was convenient (for our purposes) and easy to find. The house was extremely clean and a great set up for our family. It is a great place to relax and play!
Guest favourite
Home in Ashland
4.9 out of 5 average rating, 42 reviews

Indulgent Retreat: Pool, Hot Tub, Sauna

ChelseaRating, 5 stars4 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!
Superhost
Home in Ashland
4.75 out of 5 average rating, 16 reviews

Siskiyou Chateau

DeborahRating, 5 stars1 month ago
Spectacular views and lots of space and grandeur. Mixed art styles, some dust and clear signs of slight neglect, but mostly very well kept! All the rooms are as pictured, downtown Ashland is a 15-20 minute drive away. Some of the amenities were out of order, hard to figure out with no instructions, and /or didn’t work. Minor complaints mostly, because this is such a lovely location and property.
Guest favourite
Home in Medford
4.96 out of 5 average rating, 26 reviews

Fantastic Bright 4 Bedroom- Deck - Fireplaces

KatyRating, 5 stars1 month ago
We loved this home, have stayed in many in the area and loved the peaceful location, size of the home and the pool area. Would definitely stay again.
Superhost
Home in Central Point
4.85 out of 5 average rating, 33 reviews

Poolside Retreat W/ Sauna Heart of Wine Country

KevinRating, 5 stars1 month ago
We really loved our time at this house, we were even lucky enough to be able to extend our stay an extra day. The space inside the house is much bigger than we expected (the photos sell it a little short) and the floorplan gave everyone room to spread out and have plenty of privacy. The backyard pool area is simply amazing, it felt like we were in our own little resort. This house offered exactly what our family needed, plenty of space, outdoor amenities, and also pet friendly with a tranquil setting.
Top Guest favourite
Home in Ashland
4.95 out of 5 average rating, 96 reviews

The Aloha House - Hot Tub - Pool

ReneRating, 5 stars1 week ago
Google maps took us right to the location which was great. Kyle was kind to greet us and show us the ropes. We were able to relax and enjoy all the place has to offer for a couple of days. Comfortable beds, pillows, and linens. Kitchen stocked with so many items. Clear instructions for all the things you’d need them for. Lovely stay!

Weekly house rentals

Top Guest favourite
Home in Central Point
5 out of 5 average rating, 26 reviews

Charming Cottage on Cedar

JanRating, 5 stars2 days ago
Very nice, comfortable little cottage for two. Close to I-5, downtown Central Point and many services and restaurants. Easy 10 minute walk to town in a quiet neighborhood. The bedroom was quiet and dark with Air Con and a ceiling fan and nice queen bed. The kitchen had enough dishes, pots and pans that you could fix meals and very nice appliances. Love the fridge! Comfortable furniture for lounging. Everything was great!
Guest favourite
Home in Ashland
4.93 out of 5 average rating, 80 reviews

Abram's Cottage

SarahRating, 5 stars3 weeks ago
A lovely home with a well stocked kitchen and a great front porch and nice deck to the side. Great eat in kitchen. Walkable to town
Guest favourite
Home in Ashland
5 out of 5 average rating, 5 reviews

Aloha Farmhouse

JordanRating, 5 stars5 months ago
Amelia was so kind communicative and welcoming. The ranch was so peaceful and comforting. It brought me Into a very creative, expansive, and inspired place within myself.
Guest favourite
Home in Talent
4.96 out of 5 average rating, 24 reviews

Beautiful 3-bedroom Family House

JulieRating, 5 stars2 days ago
We were in town for our son’s graduation from SOU in Ashland, and Herrick’s place was perfect for us! Very close to downtown Ashland. House was as pictured and well-stocked. We had to ask Herrick about a couple of items when we arrived, and he was very quick to respond. We were concerned initially as it was quite warm inside when we arrived, but the AC units cooled it down very quickly once we turned them on, and they worked well throughout our stay. We would definitely stay at this property again.
Guest favourite
Home in Ashland
5 out of 5 average rating, 11 reviews

Pioneer Vacation Rentals - Pioneer North

PaigeRating, 5 stars6 months ago
Exceptional location and responsiveness from host. Walking distance to everything in town, across the street from a bakery and grocery co-op. Quiet and lovely with great heaters in winter!
Guest favourite
Home in Ashland
4.92 out of 5 average rating, 87 reviews

Charming house two blocks from downtown Ashland

MaryRating, 5 stars2 weeks ago
Quiet and private within walking distance to downtown, theater's, coffee shops, restaurants and grocery store. Beautifully decorated, very clean and very comfortable beds. Would highly recommend the Serendipity House.
Guest favourite
Home in Ashland
5 out of 5 average rating, 19 reviews

New Crowson Cottage

MichelleRating, 5 stars2 days ago
We had a lovely stay at Crowson Cottage. The home was pristine and well stocked. The side yard and patio was a great gathering spot for family joining us in town for our daughter's college graduation. We had great detailed communication before and throughout our stay.
Top Guest favourite
Home in Talent
4.96 out of 5 average rating, 27 reviews

La Casetta Tuscana

KateRating, 5 stars1 week ago
Melanies’s place is exactly as pictured- everything is pristine and new and thoughtfully decorated. The mattresses are super comfy and the kitchen has everything you need. Great communication from the host and an ideal location if you are visiting Talent or Ashland. I would go back in a heartbeat and highly recommend it!

Private house rentals

Top Guest favourite
Home in Grants Pass
5 out of 5 average rating, 36 reviews

Rogue Reefs

DrewRating, 5 stars2 weeks ago
My wife, one-year-old, and I had a wonderful stay at this Airbnb in Grants Pass during our Portland to San Francisco road trip. The location was ideal…close to great spots like Wheelhouse Coffee, downtown Grants Pass, Weekend Brewery, and beautiful southern Oregon wineries nestled in forested mountains. The Airbnb matched the listing perfectly, and Charity was a fantastic host. The hot tub was a perfect way to unwind after busy days. Highly recommend!
Top Guest favourite
Home in Ashland
5 out of 5 average rating, 15 reviews

Siskiyou Mountain Place, Ashland

AmberlyRating, 5 stars4 months ago
Our stay at Doug and Keri’s luxurious Airbnb was truly a treat! Every detail in the home was carefully thought out, creating a space that was both beautiful and welcoming. The decor, clearly Keri’s brilliant touch, made the space feel warm and homey while maintaining a sense of elegance. The view was lovely, and everything was spotless and perfectly in place. Doug was incredibly friendly and made communication a breeze, making us feel right at home. This was easily one of the best stays we’ve ever had, and we can’t recommend it enough!
Top Guest favourite
Home in Jacksonville
4.98 out of 5 average rating, 61 reviews

Historic 1875 Kitchen House

SarahRating, 5 stars3 days ago
Cyd was friendly and her place is a fun space with a lot of character. Her yard is so gorgeous and well cared for. The area is walkable to any store of your choosing and the night skies are dark and mostly free of light pollution.
Top Guest favourite
Home in Medford
5 out of 5 average rating, 11 reviews

Fieldside~king bed~pingpong

AveryRating, 5 stars3 weeks ago
True Serenity! My family and I enjoyed our stay at Hao’s place. From the morning coffee looking into a beautiful field of gold to the evenings with a cocktail enjoying the sunset. The unit was clean neat and orderly. All The amenities you could want in the kitchen and a delightful playroom in the garage. The unit is so close to all the shops and was in the perfect location for our travels. We were able to visit Mt. Shasta, Lassen Volcano, Crater Lake and The Redwoods! What a wonderful time in Medford and a great host. If we are ever back in the area we will be staying at Hao’s place!
Guest favourite
Home in Talent
4.83 out of 5 average rating, 36 reviews

Cedar house close to downtown Ashland with Sauna

AshleyRating, 5 stars2 weeks ago
Our original booking canceled on us and Eric was very responsive and helpful when we had to book last minute. The house was very clean and comfortable. Eric was responsive and provided plenty of communication and information for our stay.
Top Guest favourite
Home in Ashland
4.92 out of 5 average rating, 52 reviews

Charming Space Next to Everything, Walk Anywhere!

OlegRating, 5 stars3 weeks ago
We couldn’t have imagined a better place for our stay. Amazing location— just a block from co-op and very close to many coffee shops and great restaurants. Nearby parks and plenty of stuff to do in the area. We loved the king size bed! The kitchen was full of good quality pots, pans. Beautiful hand made ceramics and quality antique furniture all around the house. Nice large deck out front. Will book again!
Top Guest favourite
Home in Ashland
5 out of 5 average rating, 16 reviews

Historic Dunn Ranch Ashland Or.

JennyRating, 5 stars1 week ago
We had the most wonderful weekend at Jeff’s place. The home was spotless, the beds were incredibly comfortable, and everything was fully stocked with what we needed. Even though it was a very hot weekend, the house stayed cool and comfortable - I loved that each upstairs bedroom had its own mini split A/C unit! We spent hours playing foosball, shooting pool, and gathering around the big dining table. It was a multigenerational trip with family from age 3 to 83, and there was truly something for everyone - my little nieces loved the coloring station in the mudroom! Jeff has created such a cozy & welcoming space. We can’t wait to come back!
Top Guest favourite
Home in Medford
5 out of 5 average rating, 59 reviews

Luxury Guest House in Charming Old East Medford

DevanRating, 5 stars1 week ago
Sherry and Tom's Airbnb is a great place if you want a quiet stay and loves to cook at home. After I arrived check in was smooth and easy place was very clean and spacious like advertised. During my stay they were very accommodating whenever I needed help. Overall the place looked great for the price is was advertised at. In which myself I will be coming back to stay again.

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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  3. Oregon
  4. Jackson County
  5. Ashland
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