Ashland Vacation Rentals from $195: Search Short-Term Rentals

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Our top choices for Ashland vacation rentals

1. Grandview of Ashland

Ashland

Paul

$414 nightly

Aug 16 - Aug 17

Total with taxes and fees

2. A Cowslip's Belle Inn

Ashland

Daniel

$261 nightly

Aug 26 - Aug 27

Total with taxes and fees

Grand House | Living area | 65-inch TV with digital channels, streaming services

3. The Mountain Ave House by WanderLodges

Ashland

Joyce

$342 nightly

Aug 10 - Aug 11

Total with taxes and fees

4. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

Randal

$372 nightly

Aug 10 - Aug 11

Total with taxes and fees

Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, WiFi (free)

5. Barclay Klum House by WanderLodges

Ashland

Melissa

$316 nightly

Aug 9 - Aug 10

Total with taxes and fees

6. Chateau Herbe ~ Oberon Suite w/ Kitchen

Ashland

Larry D.

$248 nightly

Aug 9 - Aug 10

Total with taxes and fees

7. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

Suzanne

$282 nightly

Aug 24 - Aug 25

Total with taxes and fees

8. East Main Downtown Bungalow

Historic Railroad District

Hope S.

$196 nightly

Aug 31 - Sep 1

Total with taxes and fees

9. Chateau Herb ~ Miranda Carriage House Apt

Ashland

"Loved loved loved staying here and had a fantastic stay with very reasonable rates! It is a bit difficult to find where the apartment was, but once we figured that part out, everything fell right into place. Huge thank you to the hosts for their excellent and timely communication- I also was a huge fan of the easy check in and check out process. Views are spectacular in this area and make for a really special and beautiful stay."

Cameron A.

$248 nightly

Aug 9 - Aug 10

Total with taxes and fees

10. Hanna's House by WanderLodges

Historic Railroad District

David

$221 nightly

Aug 10 - Aug 11

Total with taxes and fees

11. 1907 Charmer, Perfect Downtown Location, So Clean!

Historic Downtown District

Virginia I.

$574 nightly

Aug 27 - Aug 28

Total with taxes and fees

12. Quaint Downtown Ashland Studio- pet friendly!

Ashland

Ralph

$236 nightly

Aug 18 - Aug 19

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi (free), bed sheets

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

Siskiyou-Hargadine Historic District

Karen G.

$226 nightly

Aug 24 - Aug 25

Total with taxes and fees

14. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

$258 nightly

Aug 17 - Aug 18

Total with taxes and fees

15. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

$217 nightly

Aug 25 - Aug 26

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

16. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Ashland

Matthew

$464 nightly

Aug 10 - Aug 11

Total with taxes and fees

2 bedrooms, desk, iron/ironing board, travel crib

17. 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

Denise

$309 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

Ashland

Casey K.

$387 nightly

Aug 9 - Aug 10

Total with taxes and fees

1 bedroom, iron/ironing board, WiFi, bed sheets

19. The Matriarch| Suite 3 | Pet friendly

Historic Railroad District

Daniel

$221 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

Historic Railroad District

Jim L.

$271 nightly

Aug 10 - Aug 11

Total with taxes and fees

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Top Ashland Hotel Reviews

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

8/10 Good

"Staff was great, and parking was convenient. The room was clean, though the bedding could be improved. Breakfast could also be improved with more fresh, locally made items and less packaging."

Ashland Hills Hotel & Suites

8/10 Good

"We've stayed here many times on our trips up and down between the Bay Area and Portland. There is lots of parking, convenient access to the freeway and very good food in the restaurant. We missed the complimentary breakfast this year. Word was the hotel recently changed owners. They are very pet friendly which is a plus for us and the fridge and microwave in the room is so helpful. The cleanliness is tops and the grounds are very nice. It's still our go to place in Ashland."

Stratford Inn

10/10 Excellent

"Everything was up to snuff except the comfort of the chairs in the guest room. Breakfast was healthy with plenty of room. The halls and rooms were exceptionally clean. We appreciated their efforts toward operating with “green” principles. The staff was friendly to a person and seemed to be interested in us as people."

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"The room was very spacious. The bed very comfortable. The location is excellent - walk to everything. Breakfast was good and plentiful with good food choices. The lobby is large well furnished and clean. Suggested improvements: larger bar of soap; a small bottle of lotion, and small half and half cream cups for the coffee."

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $195 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation 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 vacation.

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.

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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 acclaimed theater 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 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 Gorgeous Lakeside BarnHOUSE + SAUNA! and Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!.

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 Thomas Theatre, whereas Lithia Park and North Mountain Park are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Emigrant Lake 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. Grandview of Ashland

2. A Cowslip's Belle Inn

3. The Mountain Ave House by WanderLodges

4. Savage Upon Siskiyou

5. Barclay Klum House by WanderLodges

6. Chateau Herbe ~ Oberon Suite w/ Kitchen

7. Courtside Cottage - WalkScore 93 - Dog Friendly

8. East Main Downtown Bungalow

9. Chateau Herb ~ Miranda Carriage House Apt

10. Hanna's House by WanderLodges

11. 1907 Charmer, Perfect Downtown Location, So Clean!

12. Quaint Downtown Ashland Studio- pet friendly!

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

14. The Ashland Cottage, walk to town

15. Charming carriage house in Ashland near downtown

16. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

17. 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!

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

19. The Matriarch| Suite 3 | Pet friendly

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

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

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

Find out more about Ashland

Explore a world of travel with Expedia

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