Ashland Holiday Rentals

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Our top choices for Ashland holiday rentals

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7)
"Great ~ memorable stay. "
United States
Melissa
The price is AU$384
includes taxes & fees
3 Jan - 4 Jan 2026
Barclay Klum House by WanderLodges

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.8 out of 10, Exceptional, (40)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is AU$309
includes taxes & fees
17 Dec - 18 Dec
A Cowslip's Belle Inn

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
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 AU$620
includes taxes & fees
5 Jan - 6 Jan 2026
Grandview of Ashland

The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is AU$504
includes taxes & fees
16 Dec - 17 Dec
The Mountain Ave House by WanderLodges

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Ashland
10.0 out of 10, Exceptional, (18)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is AU$332
includes taxes & fees
28 Dec - 29 Dec
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Cozy Ashland Studio: King Bed, 1 mile from Plaza!

Cozy Ashland Studio: King Bed, 1 mile from Plaza!
Ashland
10.0 out of 10, Exceptional, (25)
"Just what was advertised. Cozy."
United States
Weston C.
The price is AU$306
includes taxes & fees
14 Dec - 15 Dec
Cozy Ashland Studio: King Bed, 1 mile from Plaza!

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Ashland
10.0 out of 10, Exceptional, (2)
"This house was so lovely and convenient. It was nice to leave the truck parked in its spot and walk to shops and restaurants. The house itself was open and comfortable with plenty of room for the both of us. And of course that kitchen had everything we could have asked for."
United States
Kami C.
The price is AU$520
includes taxes & fees
2 Jan - 3 Jan 2026
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
United States
Deirdre
The price is AU$308
includes taxes & fees
1 Jan - 2 Jan 2026
Hanna's House by WanderLodges

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (59)
"Great Location and Comfortable Unit."
United States
John V.
The price is AU$346
includes taxes & fees
8 Jan - 9 Jan 2026
Courtside Cottage - WalkScore 93 - Dog Friendly

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (34)
"Absolutely amazing! Designed well, thoughtful accommodation left to use to make our stay feel at home, and be able to enjoy Ashland. A must stay overnight while your visiting this great town."
United States
Melissa S.
The price is AU$255
includes taxes & fees
14 Dec - 15 Dec
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

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

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
Ashland
10.0 out of 10, Exceptional, (31)
"Our stay was amazing everything"
United States
annie t.
The price is AU$386
includes taxes & fees
14 Dec - 15 Dec
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Moody Ashland Escape: Luxe Suite, Copper Tub

Moody Ashland Escape: Luxe Suite, Copper Tub
Historic Railroad District
10.0 out of 10, Exceptional, (2)
"We really enjoyed our overnight stay. The place is centrally located, easy walking distance to downtown, and cozy. We loved the heated bathroom floors and the decor. Nice off street parking. Highly recommend. "
United States
Jon W.
The price is AU$322
includes taxes & fees
11 Jan - 12 Jan 2026
Moody Ashland Escape: Luxe Suite, Copper Tub

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
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 AU$332
includes taxes & fees
14 Dec - 15 Dec
Chateau Herb ~ Miranda Carriage House Apt

Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (6)
"Enjoyed our stay"
United States
Julie M.
Charming carriage house in Ashland near downtown

Luxury Ashland Mountain Escape: Pool, Hot Tub

Luxury Ashland Mountain Escape: Pool, Hot Tub
Ashland
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.
The price is AU$1,637
includes taxes & fees
14 Dec - 15 Dec
Luxury Ashland Mountain Escape: Pool, Hot Tub

Hot tub | Sauna |Firepit |Sleeps 6!

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
10.0 out of 10, Exceptional, (3)
"Great home in a nice location with a wonderful view. Well-appointed and clean. "
United States
Ryan G.
The price is AU$717
includes taxes & fees
5 Jan - 6 Jan 2026
Hot tub | Sauna |Firepit |Sleeps 6!

Swank House -Downtown Suite- Pet Friendly

Swank House -Downtown Suite- Pet Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (4)
"My favorite Ashland stop"
United States
Andrea T.
The price is AU$261
includes taxes & fees
6 Jan - 7 Jan 2026
Swank House -Downtown Suite- Pet Friendly

Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland
The price is AU$551
includes taxes & fees
14 Dec - 15 Dec
Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
Ashland
10.0 out of 10, Exceptional, (2)
"My daughter lives in the area. Five adults stayed here for 3 nights. Beautiful location! Everyone loved the hot tub"
United States
Natalie N.
The price is AU$416
includes taxes & fees
14 Dec - 15 Dec
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.

Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!

Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!
Siskiyou-Hargadine Historic District
9.6 out of 10, Exceptional, (11)
"The place was amazing. Within walking distance to The Cabaret Theater and many wonderful restaurants. "
United States
Denise
The price is AU$446
includes taxes & fees
14 Dec - 15 Dec
Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!
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 favourite 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 depend 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 AU$300 per night. Entering your travel dates in the search wizard might find you 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.