A deer on a road with vegetation on the sides.

Search Holiday Rentals in Ashland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Ashland holiday rentals

1. Whimsy on B

Whimsy on B
3.0 star property
Historic Railroad District
The price is £122
includes taxes & fees
18 Nov - 19 Nov
Whimsy on B

2. Whimsy On B 2br & Studio

Whimsy On B 2br & Studio
2.5 star property
Historic Railroad District
The price is £239
includes taxes & fees
16 Nov - 17 Nov
Whimsy On B 2br & Studio

3. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is £191
includes taxes & fees
12 Nov - 13 Nov
Barclay Klum House by WanderLodges

4. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Great cottage in an awesome location!"
United States
Andrea R.
The price is £179
includes taxes & fees
1 Dec - 2 Dec
Courtside Cottage - WalkScore 93 - Dog Friendly

5. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is £142
includes taxes & fees
16 Nov - 17 Nov
Hanna's House by WanderLodges

6. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is £218
includes taxes & fees
14 Nov - 15 Nov
The Ashland Cottage, walk to town

7. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
The price is £272
includes taxes & fees
2 Dec - 3 Dec
Grandview of Ashland

8. 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, (63 reviews)
"This is an excellent place to stay. It is well equipped with everything you might need for your stay. And the location is perfect."
United States
Karen G.
The price is £139
includes taxes & fees
16 Nov - 17 Nov
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

9. The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
9.8 out of 10, Exceptional, (30 reviews)
"A great place to call home while you're away from home."
United States
Tara M.
The price is £139
includes taxes & fees
16 Nov - 17 Nov
The Ashland Social | Guest Studio

10. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is £220
includes taxes & fees
17 Nov - 18 Nov
The Mountain Ave House by WanderLodges

11. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (14 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is £157
includes taxes & fees
18 Nov - 19 Nov
Charming carriage house in Ashland near downtown

12. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (56 reviews)
"Fantastic spot, walkable to anything in downtown. Well-appointed, clean, easy. Definitely recommend."
United States
Melissa D.
The price is £157
includes taxes & fees
18 Nov - 19 Nov
East Main Downtown Bungalow

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

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Historic Downtown District
9.8 out of 10, Exceptional, (138 reviews)
"Lovely property, accommodations, and location."
United States
Elaine H.
The price is £197
includes taxes & fees
14 Nov - 15 Nov
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

14. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is £262
includes taxes & fees
15 Nov - 16 Nov
Savage Upon Siskiyou

15. Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (18 reviews)
"Perfect spot to walk to the shows at OSF, walk Lithia Park, and eat and shop at all the downtown spots. Comfortable bed, quiet place, we will try to book this again for our next OSF trip!"
United States
Lara G.
Quaint Downtown Ashland Studio- pet friendly!

16. Hanna`s House | Downtown Retreat, Steps to OSF

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
10.0 out of 10, Exceptional, (171 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
The price is £159
includes taxes & fees
16 Nov - 17 Nov
Hanna`s House | Downtown Retreat, Steps to OSF

17. The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Historic Railroad District
10.0 out of 10, Exceptional, (1 review)
"The sights stunning, the garden a delight & the jacuzzi soak enriched my soul & ailing body"
United States
David B.
The price is £152
includes taxes & fees
16 Nov - 17 Nov
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

18. Affordable Luxury- One block to Downtown

Affordable Luxury- One block to Downtown
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Perfect location- We typically visit twice a year and like to stay in railroad district as it is close to restaurants and OSF. Highly recommend Swank House."
United States
Sue K.
The price is £118
includes taxes & fees
16 Nov - 17 Nov
Affordable Luxury- One block to Downtown

19. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.6 out of 10, Exceptional, (25 reviews)
"Just a little cleaner exterior"
United States
David
The price is £175
includes taxes & fees
15 Nov - 16 Nov
Chateau Herbe ~ Oberon Suite w/ Kitchen

20. The Matriarch| Suite 3 | Pet friendly

The Matriarch| Suite 3 | Pet friendly
Historic Railroad District
9.6 out of 10, Exceptional, (8 reviews)
"We stayed one night and walked easily to a show in one of the Shakespeare theatres. The apartment was super-comfortable and excellent in every way! Highly recommended!"
United States
Daniel
The price is £143
includes taxes & fees
15 Nov - 16 Nov
The Matriarch| Suite 3 | Pet friendly
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.
Save an average of 15% on thousands of hotels when you're signed in

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, apart-hotels, 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 £118 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 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?

Premier Downstairs Flat in Perfect Down Town Location : This highly rated holiday home rental in Ashland is located in the city centre, and offers a balcony, air conditioning and laundry facilities 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. Some other homes for rent in Ashland include Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly and Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. .

How many holiday rentals are there in Ashland?

Choose from 106 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Oregon Cabaret Theatre 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.