Ashland Holiday Rentals

  • 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

Check prices for these dates

Holiday Rentals in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (30)
"Lovely place and the room had everything I needed. "
The price is AU$351
includes taxes & fees
20 Feb - 21 Feb
A Cowslip's Belle Inn

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (34)
"super cool"
The price is AU$963
includes taxes & fees
21 Feb - 22 Feb
Charming home, w/hot tub, close to downtown Pet-Friendly!

Ashland Lodge w/ Lake Views & Game Room Loft

10.0 out of 10, Exceptional, (68)
"Our family and friends had the best time. Would recommend to anyone that is looking for some peace and quiet. "
Ashland Lodge w/ Lake Views & Game Room Loft

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

9.8 out of 10, Exceptional, (104)
"Owner very responsive to solve issues. Lovely place. Well stocked. Very comfortable. Very convenient. Thank you!"
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Premier Downstairs Flat in Perfect Down Town Location

10.0 out of 10, Exceptional, (48)
"Great location - close to restaurants and shops! "
Premier Downstairs Flat in Perfect Down Town Location

The Urban Gypsy Loft

10.0 out of 10, Exceptional, (1)
"This 2 bedroom flat is very spacious, with plenty of room to relax and enjoy your company. The front room has a dining area, and spacious sitting area overlooking Main Street. There is a tv room, 2 bedrooms and a kitchen. It’s is a very cozy, comfortable and homey flat. Walking distance to everywhere is downtown Ashland. The street noise is a factor. The host has supplied everything possible to make it tolerable. We were not bothered by it, but it is like staying centrally in a city environment....
The price is AU$450
includes taxes & fees
20 Feb - 21 Feb
The Urban Gypsy Loft

Hanna's House | 1 block to downtown!

10.0 out of 10, Exceptional, (162)
"Hanna's House was welcoming and comfortable from the minute I walked in the door. A mini home away from home. Fully furnished kitchen, new appliances, Sara's sweet notes throughout the house, every pillow option possible on the very comfy bed. Just beautiful! Thank you so very much, Sara."
The price is AU$465
includes taxes & fees
23 Feb - 24 Feb
Hanna's House | 1 block to downtown!

East Main Downtown Bungalow

9.4 out of 10, Exceptional, (25)
"We really enjoyed our short stay here! The cottage is clean, in a great location for walking to OSF and great food, and in a good neighborhood. Communication with the owner/manager was very easy and they were responsive to our few questions. We hope to return in 2025 for a longer visit!"
The price is AU$415
includes taxes & fees
1 Mar - 2 Mar
East Main Downtown Bungalow

Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!

10.0 out of 10, Exceptional, (5)
"Amazing stay with beautiful views. Deep in the mountains better than expected.. would recommend to anyone looking to stay in a getaway in Ashland"
Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!

In the historic railroad district, walking distance to all the best of Ashland!

10.0 out of 10, Exceptional, (176)
"This small cozy house was perfect for our group over the Thanksgiving Holiday. Great kitchen with every item we needed. Cannot beat the location. We will be back."
In the historic railroad district, walking distance to all the best of Ashland!

Downtown Delight: 3BDR Urban Escape

10.0 out of 10, Exceptional, (15)
"We were a family group in town to visit our sister several miles away. This home was lovely, well-equipped, super comfortable. The neighborhood was very quiet with dedicated parking. The upstairs bedrooms were a bit overheated at night and the floors / stairs creaked as mentioned by other reviewers, but nothing out of the norm for an older house. Will definitely try to stay here again!"
Downtown Delight: 3BDR Urban Escape

Hyatt Lake Mountain Retreat

9.8 out of 10, Exceptional, (76)
"The cabin was comfortable, clean, and our family of four had plenty of room. We would certainly book again!"
Hyatt Lake Mountain Retreat

Gorgeous Lakeside HOUSE + Indoor SAUNA!

The price is AU$588
includes taxes & fees
17 Mar - 18 Mar
Gorgeous Lakeside HOUSE + Indoor SAUNA!

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

9.6 out of 10, Exceptional, (66)
"Address and location of house was not correct, but we found it behind the house with our address. The VRBO address does not match the actual house location. Two coffee pots that did not work. After some convincing we were brought a new one. Five women stayed so a few more towels would have been helpful. And, no access to washer and dryer if your visit is short ( that should be noted in the description). Overall , we really enjoyed our stay and the location was great!"
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

1907 Charmer, Perfect Downtown Location, So Clean!

9.4 out of 10, Exceptional, (114)
"We thoroughly enjoyed our stay in this quaint home. It was very clean and comfortable. We loved being able to walk to numerous restaurants, and to the theaters for the Oregon Shakespeare Festival! Alla was easily accessible via messaging, and when a couple of repair issues arose, she responded quickly and made sure the issues were addressed completely in a timely manner. Thank you, Alla and Patrick, for making this lovely house available to Ashland visitors! It helped facilitate a very special...
1907 Charmer, Perfect Downtown Location, So Clean!

The Red Dragon House

10.0 out of 10, Exceptional, (87)
"The owners provided detailed instructions on how to find and access the property. The home is delightfully decorated with dragons galore. I considered counting them all, but soon gave up the plan as too time-consuming! The property feels remote, with views of the hills. The house is surrounded by grass, trees, and a fence obscuring the farther houses. We couldn’t hear the freeway from the house. The hosts live next door, and greeted us briefly when we arrived. Mike introduced us to their horses,...
The price is AU$320
includes taxes & fees
20 Feb - 21 Feb
The Red Dragon House

The Ashland Cottage, walk to town

10.0 out of 10, Exceptional, (191)
"We'll be back!"
The price is AU$461
includes taxes & fees
23 Feb - 24 Feb
The Ashland Cottage, walk to town

Cedar Wood Mountain View Retreat

10.0 out of 10, Exceptional, (3)
"We rented the house during Christmas break and it was absolutely wonderful for our large family. Everyone had enough sleeping space, the house was clean, cozy, and welcoming. The view of the mountains and countryside is also a plus! Everything worked out - and the hot tub was a nice addition. The house is even stocked with toys and books for children and plenty of towels and linens. We enjoyed cooking in kitchen as well. This is a great spot! "
Cedar Wood Mountain View Retreat

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

10.0 out of 10, Exceptional, (13)
"This is such a lovely getaway! We really enjoyed the space, the beds were super comfy, everything was super clean, and the addition of a bunch of available indoor annd outdoor games and toys really took it up a notch! We had 2 under 2yo kiddos with us who also really seemed to enjoy the space and feel right at home! The hosts were communicative and so kind. We would love to see the check-out instructions displayed more clearly as we found it hard to decipher just that pertinent information! We...
The price is AU$401
includes taxes & fees
20 Feb - 21 Feb
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Entire Inn | Hot Tub | Downtown Ashland | Tesla Station

The price is AU$1,508
includes taxes & fees
20 Feb - 21 Feb
Entire Inn | Hot Tub | Downtown Ashland | Tesla Station
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.
Don't see what you're looking for?
See all available properties in Ashland
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Ashland you may be interested in

Stratford Inn

2.5 star property
9.2 out of 10, Wonderful, (1530)
"Friendly staff great location "
The price is AU$149
includes taxes & fees
24 Feb - 25 Feb
Stratford Inn

Ashland Hills Hotel & Suites

3.0 star property
9.0 out of 10, Wonderful, (1475)
"NICE!"
The price is AU$186
includes taxes & fees
10 Mar - 11 Mar
Ashland Hills Hotel & Suites

Ashland Springs Hotel

3.0 star property
9.4 out of 10, Exceptional, (1000)
"It’s the only place I stay when I’m in southern Oregon. "
The price is AU$263
includes taxes & fees
24 Feb - 25 Feb
Ashland Springs Hotel
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.

Frequently asked questions

Can I find holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to ScienceWorks Hands-On Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theatre scene this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best holiday rentals that Ashland has to offer?

Charming home, w/hot tub, close to downtown Pet-Friendly!: This highly rated holiday home rental in Ashland offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Some other homes for rent in Ashland include Ashland Lodge w/ Lake Views & Game Room Loft and Gorgeous Lakeside HOUSE + Indoor SAUNA!.

How many holiday rentals are there in Ashland?

Choose from 107 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Oregon Shakespeare Festival, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Cabaret Theatre and Ashland Library are other places to visit while you're in town.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family getaway.