Ashland Holiday Rentals from AU$277: Search Short-Term Rentals

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Our top choices for Ashland holiday rentals

A two-story house with a prominent staircase leading to the entrance.

1. Barclay Klum House by WanderLodges

Ashland

Melissa

includes taxes & fees

29 Nov - 30 Nov

A house with a wooden deck, a stone wall, and a wooden fence.

2. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

includes taxes & fees

2 Dec - 3 Dec

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

3. The Mountain Ave House by WanderLodges

Ashland

Joyce

includes taxes & fees

4 Nov - 5 Nov

A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

4. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

Andrea R.

includes taxes & fees

1 Dec - 2 Dec

A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

5. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

includes taxes & fees

22 Nov - 23 Nov

A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

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

Historic Downtown District

Elaine H.

includes taxes & fees

7 Nov - 8 Nov

A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

7. Chateau Herbe ~ Oberon Suite w/ Kitchen

Ashland

David

includes taxes & fees

4 Nov - 5 Nov

A deck with a fire pit, outdoor seating, and a view of the countryside.

8. Grandview of Ashland

Ashland

Jose

includes taxes & fees

2 Dec - 3 Dec

A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

9. East Main Downtown Bungalow

Historic Railroad District

Amy R.

includes taxes & fees

4 Nov - 5 Nov

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

10. Hanna's House by WanderLodges

Historic Railroad District

Robert

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

11. Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Siskiyou-Hargadine Historic District

Karen G.

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

12. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

includes taxes & fees

29 Nov - 30 Nov

A modern bedroom with a large bed, wooden slatted ceiling, a flat-screen TV, and a built-in wardrobe.

13. Swank House -Downtown Suite- Pet Friendly

Historic Railroad District

Katie I.

includes taxes & fees

4 Nov - 5 Nov

A living room with a green sofa, a television, a wooden coffee table, and a patterned rug.

14. The Matriarch| Suite 3 | Pet friendly

Historic Railroad District

Daniel

includes taxes & fees

4 Nov - 5 Nov

A porch with wicker furniture, a small table, and a plaid rug.

15. Affordable Luxury- One block to Downtown

Historic Railroad District

Sue K.

16. 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.

Siskiyou-Hargadine Historic District

Adam B.

A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

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

Historic Railroad District

Jim L.

includes taxes & fees

8 Nov - 9 Nov

A covered outdoor area with a stone pathway, a wooden railing, and a green chair.

18. Quaint Downtown Ashland Studio- pet friendly!

Ashland

Lara G.

includes taxes & fees

4 Nov - 5 Nov

A modern bathroom with a glass shower enclosure, a sink with a mirror, and a decorative wall with floral patterns.

19. Moody Ashland Escape: Luxe Suite, Copper Tub

Historic Railroad District

Nancy

includes taxes & fees

4 Nov - 5 Nov

A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

20. The Ashland Social | Guest Studio

Ashland

Tara M.

includes taxes & fees

8 Nov - 9 Nov

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Top Ashland Hotel Reviews

Holiday Inn Express & Suites Ashland by IHG

8/10 Good

"The rooms were really nice and clean with a newer feel in the room. The staff was helpful at the front desk and the breakfast in the morning had good selections."

Stratford Inn

10/10 Excellent

"The Stratford in is a great spot. This is a throw back style hotel where the human element is still alive and well. The staff was engaged and very friendly. The hotel is clean, well maintained, and quiet. There are great touches like actual glasses and coffee mugs for your use and higher quality food and coffee offered for the breakfast. The pool is a salt water heated pool and is a great amenity. The theming and decor is fun. The hotel is very walkable to lots of restaurants and coffee shops - pretty much anything you'd do in Ashland. We look forward to staying there again in the future."

Lithia Springs Resort

10/10 Excellent

"I don’t suggest having the breakfast. The eggs were super salty and had onions mixed in with the scramble. The scones were raw inside. The oatmeal was slimy with a film of wet water over the top. But don’t let that stop you from staying. Just drive 7 minutes down 99 and visit one of Ashlands amazing breakfast coffee restaurants."

Timbers INN and Suites

10/10 Excellent

"Place is super cute. Getting in and out is a bit of a pain, tiny parking area, but it was manageable. The water pressure was really good. Oddly, it varied regularly, alternating between a lowish (but usable) flow to something much more forceful. That was my only half-complaint. Even at its lowest, it was still nice and hot and well within normal standards. Room was spacious, bed was nice. I would definitely stay here again."

Ashland Motel - Oregon

8/10 Good

"Rooms are clean and have window ac units. Bathroom is a decent size and shower is amply large. Free parking available. No housekeeping offered for first four days and rarely is anyone in the office. On our last day, someone knocked on the door and asked us if we needed housekeeping, but we were leaving the next day so that wasn’t helpful. Desk area is useful and there is an extension cord with multiple outlets by the desk."

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$277 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 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.

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Check prices for these dates

Our top choices for Ashland holiday rentals

1. Barclay Klum House by WanderLodges

2. The Ashland Cottage, walk to town

3. The Mountain Ave House by WanderLodges

4. Courtside Cottage - WalkScore 93 - Dog Friendly

5. Savage Upon Siskiyou

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

7. Chateau Herbe ~ Oberon Suite w/ Kitchen

8. Grandview of Ashland

9. East Main Downtown Bungalow

10. Hanna's House by WanderLodges

11. Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

12. Charming carriage house in Ashland near downtown

13. Swank House -Downtown Suite- Pet Friendly

14. The Matriarch| Suite 3 | Pet friendly

15. Affordable Luxury- One block to Downtown

16. 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.

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

18. Quaint Downtown Ashland Studio- pet friendly!

19. Moody Ashland Escape: Luxe Suite, Copper Tub

20. The Ashland Social | Guest Studio

Find holiday rentals that suit your style

Top Ashland Hotel Reviews

Holiday Inn Express & Suites Ashland by IHG

Stratford Inn

Lithia Springs Resort

Timbers INN and Suites

Best Western Windsor Inn

Callahan's Mountain Lodge

The Bard's Inn, BW Signature Collection by Best Western

Ashland Motel - Oregon

Ashland Commons Hostel

Find out more about Ashland

Frequently asked questions

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