House holiday rentals in Ashland

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Popular amenities for house rentals in Ashland

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 stars6 days ago
The house is lovely and Amanda was very responsive!
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 stars5 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.
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, 97 reviews

The Aloha House - Hot Tub - Pool

SusanRating, 5 stars3 days ago
A truly lovely spot! Such a beautiful and peaceful time listening to bird calls and looking out across the valley from this comfortable, light-filled modern space tucked high up in the woods. Flowering plants all around the yard, wonderful pool and hot tub. Kyle very kindly and quickly helped with a request and our stay was incredibly relaxing and serene. Gorgeous place, hope to be back soon.
Guest favourite
Home in Eagle Point
4.9 out of 5 average rating, 40 reviews

Cascade Sunset Home+HOT TUB - Crater Lake Vacation

KimRating, 5 stars1 week ago
A good base for exploring the Rogue River and Crater Lake. The house is spacious and 2 units that can be separated depending on your party size. We had 6 people and were given access to the whole house. We were only there 2 nights so didn’t try out the hot tub or pool but they look inviting. House has a coffee bar in the kitchen and plenty of kitchenware if you want to cook. The sunset views are quite pretty.

Weekly house rentals

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.
Superhost
Home in Ashland
4.81 out of 5 average rating, 123 reviews

Street Level Flat in great Downtown Location "A"

JordanRating, 5 stars6 days ago
We had a lovely week at Amber’s place. Communication with the hosts was easy, the set up of the place is very functional and comfortable, the location is amazing and overall we had a lovely time. Highly recommend.
Top guest favourite
Home in Medford
4.99 out of 5 average rating, 111 reviews

Chic 4 bed/2 bath house with large yard

MarcyRating, 5 stars3 days ago
This place was amazing. Our whole family loved and enjoyed each minute. The back yard was peaceful. Our family played in the backyard, ate together, and enjoyed the privacy. We had to extend our stay a few more days. The request to extend was responded to quite fast and approved. We come to this area quite often and will be staying here moving forward.
Guest favourite
Home in Ashland
5 out of 5 average rating, 12 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, 88 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 stars6 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.
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 Talent
4.97 out of 5 average rating, 29 reviews

La Casetta Tuscana

MeaghanRating, 5 stars1 week ago
La Casetta Tuscana is a lovely home. It is small, but very comfortable, and I loved the color schemes and decoration. The kitchen had everything we needed to cook, and the washer/dryer was great to have. Melanie was a wonderfully communicative and generous host. Check out Cafe Soleil for coffee! A few small things to be aware of: the back bedroom has a high transom window that doesn't have a curtain that blocks any light, so you will be rising early. The climate control is via wall units, one in the back bedroom and one in the living room. They are very effective in those spaces, but I'm not sure how well the front bedroom will cool down on hot days (there is auxiliary heat that works great!). The neighborhood is a bit busy, and you do hear your neighbors. It isn't particularly private, in part because the area is recovering from a massive fire, so there aren't trees to cushion sound. There is one house still unfinished on the street, but we heard no construction while we were there.

Private house rentals

Guest favourite
Home in Talent
4.96 out of 5 average rating, 24 reviews

Beautiful 3-bedroom Family House

JulieRating, 5 stars6 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
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
Top guest favourite
Home in Grants Pass
5 out of 5 average rating, 38 reviews

Rogue Reefs

EasterRating, 5 stars3 days ago
Our stay was amazing and memorable. The location is right against the Rogue river where boat tours pass by. The scenery is gorgeous. The beautiful Redwood trees and what I believe to be an exotic bird at one of the neigbora, happily singing, along with the freshness of the great outdoors gave us a feeling of being in the tranquility. This is our first time staying in Oregon and I have to say everyone is very pleasant and polite. The inside of your home made me feel right at home. With all the amenities that one would need plus the huge upside is there was enough space for my teenage daughters to be under one roof and BE happy (smiling ❤️) We had a wondeful time. We would stay here again the next time we visit.
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 Medford
5 out of 5 average rating, 33 reviews

The Disco Daizy

KatieRating, 5 stars1 week ago
What a fun and beautiful house! I rented the Disco Daisy for a girls trip and it was perfect. Cute,Cozy, and the decor was amazing. All of the beds were so comfortable and the backyard space was a fun place to hangout at night. We’ll definitely be coming back!
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 Central Point
4.96 out of 5 average rating, 51 reviews

Modern cozy home

DebraRating, 5 stars3 months ago
This was my third time renting this unit in the last three months and would rent it again any time I need a spot in Central Point, which I believe says a lot about how much I appreciate this little gem! 💎
Top guest favourite
Home in Medford
5 out of 5 average rating, 59 reviews

Luxury Guest House in Charming Old East Medford

DevanRating, 5 stars2 weeks 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

  • Wifi availability

    100 properties include access to wifi

Destinations to explore

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