Ashland Holiday Rentals

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Our top choices for Ashland holiday rentals

Holiday Home in Historic Railroad District

New Downtown 3 Bedroom Upstairs Flat with views
9.8 out of 10, Exceptional, (33)
"Had a great time. Would stay again!"
United States
Tracy L.
New Downtown 3 Bedroom Upstairs Flat with views
10.0 out of 10, Exceptional, (61)
"Perfect spot.We really enjoyed our stay."
United States
Cecilia K.
The price is NZ$867
includes taxes & fees
12 Dec - 13 Dec
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
9.6 out of 10, Exceptional, (19)
"We loved "
United States
Phyllis M.
The price is NZ$696
includes taxes & fees
12 Dec - 13 Dec
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

Apartment in Siskiyou-Hargadine Historic District

The Maple Apartment at Tudor House Vacation Rentals
9.6 out of 10, Exceptional, (155)
"Quiet, comfortable, great place for 3 friends. Easy walk to downtown Ashland & OSF. The off-street parking was a bonus. "
United States
Stephanie M.
The Maple Apartment at Tudor House Vacation Rentals
8.8 out of 10, Excellent, (5)
"House was very clean and taken care of. A beautiful destination right across the street from lake access. Went down with a group and had an excellent stay!"
United States
Hannah D.
The price is NZ$614
includes taxes & fees
14 Dec - 15 Dec
Gorgeous Lakeside HOUSE + Indoor SAUNA!
9.6 out of 10, Exceptional, (4)
"Nice place to stay, with full kitchen, and a close drive to downtown Ashland. The AC stopped and the staff were very responsive and provided."
United States
Catherine J.
The price is NZ$377
includes taxes & fees
14 Dec - 15 Dec
Chateau Herb ~ Miranda Carriage House Apt

Holiday Home in Ashland

Grandview of Ashland
3.0 star property
10.0 out of 10, Exceptional, (2)
"I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want to stay there again when I come to visit family. "
United States
Monica
The price is NZ$712
includes taxes & fees
5 Jan - 6 Jan 2026
Grandview of Ashland
9.4 out of 10, Exceptional, (16)
"Excellent place to stay. Grounds were stunning and the chateau felt cozy and private. "
United States
Timothy W.
The price is NZ$380
includes taxes & fees
14 Dec - 15 Dec
Chateau Herbe ~ Oberon Suite w/ Kitchen

Holiday Home in Ashland

Barclay Klum House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7)
"Great ~ memorable stay. "
United States
Melissa
The price is NZ$441
includes taxes & fees
5 Jan - 6 Jan 2026
Barclay Klum House by WanderLodges

Apartment in Ashland

A Cowslip's Belle Inn
3.0 star property
9.8 out of 10, Exceptional, (40)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is NZ$355
includes taxes & fees
14 Dec - 15 Dec
A Cowslip's Belle Inn
10.0 out of 10, Exceptional, (57)
"Great, cozy cabin in a beautiful location."
United States
Sara F.
The price is NZ$709
includes taxes & fees
22 Dec - 23 Dec
Hyatt Prairie Mountain Cabin

Holiday Home in Historic Railroad District

Hanna's House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
United States
Deirdre
The price is NZ$354
includes taxes & fees
1 Jan - 2 Jan 2026
Hanna's House by WanderLodges
10.0 out of 10, Exceptional, (3)
"Great location, nice place to stay. Could use a frying pan."
United States
Karen B.
The price is NZ$600
includes taxes & fees
14 Dec - 15 Dec
Spacious 2 bedroom historic home with two king beds and kitchenette.

Cabin in Jackson County

Homey Rustic Cabin in the Cascades
10.0 out of 10, Exceptional, (1)
"Great location cabin was perfect for a group large upstairs sleeping areas. Outside was great "
United Kingdom
Troy K.
The price is NZ$605
includes taxes & fees
22 Dec - 23 Dec
Homey Rustic Cabin in the Cascades
10.0 out of 10, Exceptional, (31)
"Our stay was amazing everything"
United States
annie t.
The price is NZ$438
includes taxes & fees
14 Dec - 15 Dec
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
10.0 out of 10, Exceptional, (4)
"One night stay, very peaceful "
United Kingdom
Joshua S.
The price is NZ$515
includes taxes & fees
11 Jan - 12 Jan 2026
Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
10.0 out of 10, Exceptional, (5)
"This is our 4th time staying at the Anne Hathaway House and it is always an exceptional experience."
United States
Anne G.
The price is NZ$1,373
includes taxes & fees
17 Dec - 18 Dec
Anne Hathaway, 8 bedrooms, 9 bathrooms, a commercial kitchen and dining room.
9.4 out of 10, Exceptional, (3)
"This property was wonderful for our family of 5 teens. The kitchen was well stocked, beds comfortable and it also had a nice quiet and calm feel. Can't wait to come back. "
United States
siobhan c.
Luxury Ashland Mountain Escape: Pool, Hot Tub

Holiday Home in Ashland

The Red Dragon House
10.0 out of 10, Exceptional, (103)
"Wonderful stay, thank you!!! Our doggo felt so at home!"
United States
Kirsten P.
The price is NZ$340
includes taxes & fees
12 Dec - 13 Dec
The Red Dragon House
10.0 out of 10, Exceptional, (11)
"Close to town, very nice room. We had fun in Ashland."
United States
Adam B.
The price is NZ$405
includes taxes & fees
11 Jan - 12 Jan 2026
Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.
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.
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Top Ashland Hotel Reviews

Find out more about Ashland

Everything you need to know about Ashland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland holiday rentals we have selected for you start as low as NZ$340 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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 renowned opera 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?

Grandview of Ashland: This highly rated holiday home rental in Ashland is located near the airport, and has a garden, 1 hot tub and a BBQ to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. Other favourite homes for rent in Ashland are New Downtown 3 Bedroom Upstairs Flat with views and Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly.

How many holiday rentals are there in Ashland?

Choose from 102 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Thomas Theatre, whereas Lithia Park and Howard Prairie Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival 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.