Holiday Homes in Ashland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

Featured Holiday Homes in Ashland

Fridge, microwave, oven, stovetop
New house with king beds and 3 full bathrooms
9.6 out of 10, Exceptional, (21)
"The home was nice and in itself was clean. It is conveniently located and close to restaurants and shopping. Unfortunately they were running behind and we had to wait in our cars and werent able to check in until 430 and had zero towels to use and were left with a closet full of dirty linens. We had a 530 show to get to and were hoping to spruce up a bit but there was no time and we didnt bring our own towels. We literally didnt even have a hand towel to dry our hands in the bathroom. The owner...
The price is NZ$407
per night
14 May - 15 May
New house with king beds and 3 full bathrooms
Smart TV, books
Downtown Ashland Pet-Friendly Haven
9.6 out of 10, Exceptional, (9)
"We stayed for a week and it met all our needs. We loved the location, the beds were comfortable, the house was very clean and we felt safe. Thanks for a relaxing stay."
The price is NZ$510
per night
20 May - 21 May
Downtown Ashland Pet-Friendly Haven
Exterior
1930s Queen Anne Historic Downtown Retreat
9.8 out of 10, Exceptional, (23)
"A wonderful time at your lovely, beautifully updated home! Extremely comfortable, clean, roomy. Outstanding communication with hosts, who were very solicitous of our comfort. Great backyard for our little dog and us with patio table when weather permitted. Quiet and safe neighborhood. Highly recommend this home!!!"
The price is NZ$671
per night
27 May - 28 May
1930s Queen Anne Historic Downtown Retreat
Save an average of 15% on thousands of hotels when you're signed in
Fridge, microwave, stovetop, dishwasher
Lovely Medford Home w/ Patio, Fire Pit + Gas Grill
9.4 out of 10, Exceptional, (3)
"House was very clean and comfortable. Stocked with all the necessities to make our stay enjoyable. It was a short walk to the hospital which was the reason we selected this location. Would definitely recommend!!"
Lovely Medford Home w/ Patio, Fire Pit + Gas Grill
Property grounds
Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.
Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.
Fridge, microwave, stovetop, dishwasher
Stunning Medford Escape w/ Panoramic Views!
10.0 out of 10, Exceptional, (24)
"Cathy is Great, The home is a giant older single story Family Home with a basement full of beds and air hocky table, Huge kitchen and dining room, Hot tub, Pool, alot of toys for the pool, garage, even entry gates to the property its fenced, and surrounded by wild turkeys and deer ! It was really nice ! and they allow your Dogs ! Thanks Again Cathy!"
Stunning Medford Escape w/ Panoramic Views!
Fridge, microwave, oven, stovetop
Southern Oregon Gem (EV Charger)
10.0 out of 10, Exceptional, (27)
"The accommodations were great and very comfortable. We couldn't find any information about WiFi in the house though, and when I sent a message to the host, asking if there was WiFi his response was "yes" without any further information. Otherwise no complaints!"
The price is NZ$241
per night
19 May - 20 May
Southern Oregon Gem (EV Charger)
Fridge, microwave, oven, stovetop
Railroad District, steps to downtown, everything you need to enjoy Ashland!
10.0 out of 10, Exceptional, (129)
"Had the best stay in Ashland; went everywhere. The leaves were brilliant and bright."
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Fridge, microwave, oven, stovetop
Tastefully remodeled 3 bedroom 2 bath home with large private back yard
10.0 out of 10, Exceptional, (16)
"Perfect stopping point on our Seattle to San Francisco drive with two big dogs. They loved having the yard to stretch their legs, and we loved the (ultra clean) well appointed house. We enjoyed relaxing in the family room, catching up on some work and watching a movie. So much better than a hotel. I also appreciated having a long length of curbfront where we could pull up our pickup and trailer, without encroaching on the neighbor or having to unhitch. Very comfortable for one night, kinda...
The price is NZ$652
per night
15 May - 16 May
Tastefully remodeled 3 bedroom 2 bath home with large private back yard
Property grounds
Award Winning Britt Bungalow in the Heart of Jacksonville Oregon
9.6 out of 10, Exceptional, (14)
"Be home, exactly as present, and maybe even better than the pictures imply! The host was gracious very easy to communicate with, and very accommodating for my stay. I will definitely be back."
The price is NZ$804
per night
16 May - 17 May
Award Winning Britt Bungalow in the Heart of Jacksonville Oregon
Fridge, microwave, oven, stovetop
Premier Downstairs Flat in Perfect Down Town Location
10.0 out of 10, Exceptional, (31)
"Very, very clean home. Excellent location with very comfortable beds and all the appliances needed to create a comfortable weekend."
Premier Downstairs Flat in Perfect Down Town Location
Microwave, dishwasher
East Main Downtown Bungalow
9.6 out of 10, Exceptional, (15)
"clean and comfy bed. Overall, nice. BUT front door lock and instructions not good. The numbers on the lock are invisible. there is no obvious "home" button to push. None of which is mentioned in the instructions. Also, the sign on the top of the fridge needs attention. The headline is "Before you leave" with no hint that tenants should read it upon arrival to see the internet instructions. There is no book of further information as claimed."
The price is NZ$517
per night
19 May - 20 May
East Main Downtown Bungalow
Fridge, microwave, oven, stovetop
Welcome to our charming Hygge home in East Medford, OR
8.6 out of 10, Excellent, (4)
"Would stay again!"
Welcome to our charming Hygge home in East Medford, OR
Property grounds
A luxury retreat: Siskiyou Mountain Place, Ashland. 2 br, kitchenette
The price is NZ$418
per night
14 May - 15 May
A luxury retreat: Siskiyou Mountain Place, Ashland. 2 br, kitchenette
Beach
Large Private Carriage-House Retreat with Amazing Views
10.0 out of 10, Exceptional, (112)
"I needed a place to stay while working out of town for a couple of months. This place was everything I needed, and then some! Nice neighborhood, but close to Roxy Ann peak for hiking and close to town for everything else. Very quiet and secure neighborhood and secure parking behind a gate behind the main house. The hosts provided everything I needed, and while the "apartment" is in their backyard, it felt like I had my own place all to myself. Great sunset views across the valley, and a nice...
Large Private Carriage-House Retreat with Amazing Views
Fridge, microwave, oven, stovetop
Comfy Cozy Casa
10.0 out of 10, Exceptional, (25)
"The home was beautiful and well stocked. Beds were comfy. I will recommend this home to friends."
The price is NZ$478
per night
19 May - 20 May
Comfy Cozy Casa
Outdoor dining
Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views
9.6 out of 10, Exceptional, (32)
"Beautiful and comfortable"
Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views
Property grounds
Beautiful Luxury Cottage. Walk To It All!
10.0 out of 10, Exceptional, (101)
"This freshly renovated cottage was a good pick for our party of 3. Upon arrival, we were greeted with a lovely note from the host, a bevy of great snacks and water options in the fridge. The whole place was very stylish with high quality design choices in every room. The linens and towels were absolutely wonderful and there were thoughtful amenities supplied like thick robes and slippers, additional toiletries and nice laundry facilities. The living room was very hip, which we enjoyed, but we...
Beautiful Luxury Cottage. Walk To It All!
Fridge, microwave, oven, stovetop
Charming Space Next to Everything, Walk Anywhere!
10.0 out of 10, Exceptional, (32)
"The location is great! I was able to walk everywhere in town that I needed to go. I also loved the colorful and decorated interior."
Charming Space Next to Everything, Walk Anywhere!
5 bedrooms, WiFi
The Blue Moon House has 5 bedrooms, each with a private bath, plus kitchen, dining and living area.
The Blue Moon House has 5 bedrooms, each with a private bath, plus kitchen, dining and living area.
Don't see what you're looking for?
See all available properties in Ashland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Ashland

Smart TV, books
Downtown Ashland Pet-Friendly Haven
9.6 out of 10, Exceptional, (9)
"We stayed for a week and it met all our needs. We loved the location, the beds were comfortable, the house was very clean and we felt safe. Thanks for a relaxing stay."
The price is NZ$510
per night
20 May - 21 May
Downtown Ashland Pet-Friendly Haven
Main House | Terrace/patio
A Cowslip's Belle Inn
3.0 star property
9.8 out of 10, Exceptional, (9)
"This place is absolutely amazing. I stayed for a long weekend/Mt bike trip and really enjoyed it. Quiet, peaceful setting and close to everything. "
The price is NZ$456
per night
15 May - 16 May
A Cowslip's Belle Inn
Fridge, microwave, oven, stovetop
Hyatt Lake Mountain Retreat
9.8 out of 10, Exceptional, (65)
"The house was so cozy and comfortable. A sit on the porch swing and the lovely view of the prairie and lake! Host was so helpful and so accommodating!!"
Hyatt Lake Mountain Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.