Ashland Vacation Rentals from CA $134: Short-Term Rentals for 2026

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Our top choices for Ashland vacation rentals

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

1. Barclay Klum House by WanderLodges

Ashland

Melissa

CA $378 total

includes taxes & fees

Sep 7 - Sep 8

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

2. East Main Downtown Bungalow

Historic Railroad District

Amy R.

CA $308 total

includes taxes & fees

Sep 27 - Sep 28

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

CA $477 total

includes taxes & fees

Sep 7 - Sep 8

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

4. The Ashland Social | Guest Studio

Ashland

Tara M.

CA $282 total

includes taxes & fees

Sep 14 - Sep 15

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

CA $584 total

includes taxes & fees

Sep 2 - Sep 3

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

6. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

Suzanne

CA $404 total

includes taxes & fees

Sep 3 - Sep 4

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

7. Grandview of Ashland

Ashland

Sonja

CA $550 total

includes taxes & fees

Sep 13 - Sep 14

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

8. Hanna's House by WanderLodges

Historic Railroad District

David

CA $369 total

includes taxes & fees

Sep 10 - Sep 11

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Top Ashland Hotel Reviews

Best Western Windsor Inn

10/10 Excellent

"Everything was wonderful."

Stratford Inn

8/10 Good

"The room was spotless, the bathroom sparkled. Wood floors, no icky carpeting. Soft towels, very nice Beekman 1802 products. The only things that weren’t quite right were: one of the washcloths in the bathroom had a stain that looked bad enough that it should have been retired. Even though it was probably recently washed, no one would want to put it on their face. No big deal to us. We couldn’t get comfortable on the bed no matter how we tried. Very unusual for me. I’m a pretty good sleeper but just couldn’t settle into the bed. Breakfast was great! Plenty of serve yourself options, a nice selection of breads, bagels, etc, along with cereals, yogurt toppings etc. Very organized and clean. Over all we’d definitely go back and maybe try a different room in hopes that our problems with the mattress were just a one time issue."

Ashland Hills Hotel & Suites

8/10 Good

"1) Very Disappointed that the property does Not have Secure Internet Access That makes it very dangerous to do any financial transactions while at the Property No Stock market trading No purchases that include providing financial and personal information I DON’T UNDERSTAND HOW THERE IS NO SECURE INTERNET ACCESS WHEN THAT IS SO IMPORTANT IN TODAY’S WORLD 2) Disappointing that they No Longer have a Buffet Style Breakfast included. The Breakfast was a main stay at this property and made it more enjoyable."

Timbers INN and Suites

10/10 Excellent

"Older but clean property. Being on special diets, my friend and I both appreciated booking a room with a kitchen (fridge, stove, plates, etc) A bit of a walk to OSF campus for those not used to walking, but doable for younger folks. Does appear to be on the bus line, but we had a car. A few smaller things weren't deal breakers (bigger coffee cups) but we did have major trouble, late at night, with the room key not working. Strongly suggested to mgmt that they replace all door knobs and locks."

Find out more about Ashland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and entertainment choices 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 vacation rentals that Ashland has to offer?

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly: This highly rated vacation home rental in Ashland offers a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other homes for rent in Ashland include Beautiful bungalow downtown Ashland railroad district, rv parking, adventure! and Gorgeous Lakeside BarnHOUSE + SAUNA!.

How many vacation rentals are there in Ashland?

Choose from 108 Expedia vacation rentals in Ashland for a memorable vacation.

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 vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.

Ashland Vacation Rentals

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Check prices for these dates

Our top choices for Ashland vacation rentals

1. Barclay Klum House by WanderLodges

2. East Main Downtown Bungalow

3. The Mountain Ave House by WanderLodges

4. The Ashland Social | Guest Studio

5. Savage Upon Siskiyou

6. Courtside Cottage - WalkScore 93 - Dog Friendly

7. Grandview of Ashland

8. Hanna's House by WanderLodges

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

10. Charming carriage house in Ashland near downtown

11. Quaint Downtown Ashland Studio- pet friendly!

12. The Ashland Cottage, walk to town

13. 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.

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

15. A Cowslip's Belle Inn

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

17. Swank House -Downtown Suite- Pet Friendly

18. Chateau Herbe ~ Oberon Suite w/ Kitchen

19. Swank Suites | King with Lux Tub

20. Swank Suites + Private Porch Patio

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Best Western Windsor Inn

Find out more about Ashland

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