
House holiday rentals in Ashland
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Top-rated house rentals in Ashland
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Popular amenities for Ashland house rentals
House rentals with a pool

Rellik Wine Suite near Jacksonville Hot Tub/Pool
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.

Cherry Lane, Crystal Skies
The house is lovely and Amanda was very responsive!

Capital House - Private getaway with POOL!
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!

Indulgent Retreat: Pool, Hot Tub, Sauna
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!

Fantastic Bright 4 Bedroom- Deck - Fireplaces
This is the 3rd time we have stayed here. It is pristine, beautiful, and spacious. Very safe neighborhood. Will always check this place out first.

Siskiyou Chateau
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.

Poolside Retreat W/ Sauna Heart of Wine Country
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.

The Aloha House - Hot Tub - Pool
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.
Weekly house rentals

Aloha Farmhouse
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.

Street Level Flat in great Downtown Location "A"
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.

Pioneer Vacation Rentals - Pioneer North
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!

Charming house two blocks from downtown Ashland
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.

New Crowson Cottage
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.

Cedar house close to downtown Ashland with Sauna
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.

Charming Space Next to Everything, Walk Anywhere!
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!

La Casetta Tuscana
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

Beautiful 3-bedroom Family House
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.

Abram's Cottage
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

Siskiyou Mountain Place, Ashland
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!

Pet Friendly w/ hot tub by town!
Michael was very communicative and easy to work with, even allowing us to arrive a little early for our check-in. The neighborhood is quiet, and there's a corner grocery 60 seconds away. Downtown is 10-15 minute walk. The backyard is an absolute highlight - it's shaded and comfortable with seating and a small yard, a grill, a swingset and a hot tub, and even an outdoor shower.

The Victorian Secret
Our family stay at the Victorian Secret surpassed all expectation. We had such a great time in Ashland and having this beautiful, welcoming house as our home base was so special. The location was great for walking, we barely used the car. The house was incredibly well appointed, and seeping with charm, art and creative touches everywhere. The beds were very comfortable and the kitchen was very well stocked for cooking. Seeing deer and wild turkeys in the field across the street was a bonus that our grandkids especially enjoyed. My 6 year old granddaughter gently kissed the house goodbye as we departed and said, "I'll remember you forever!"

Modern cozy home
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! 💎

Centrally located Downtown Historic Home w/parking
We enjoyed our visit very much. The whole downtown with great restaurants, parks, trails and entertainment is an easy walk from the house. We especially enjoyed meals and groceries from the co op right behind the house. The foosball table was a hit! The house was comfortable with air conditioner units in the living room and the main bedroom that kept the house cool. We would love to stay here again.

Luxury Guest House in Charming Old East Medford
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
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