Ashland Vacation Rentals from AED 716: Search Short-Term Rentals

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Our top choices for Ashland vacation rentals

1. Grandview of Ashland

Ashland

Paul

AED 1,536 total

includes taxes & fees

16 Aug - 17 Aug

2. A Cowslip's Belle Inn

Ashland

Daniel

AED 913 total

includes taxes & fees

17 Aug - 18 Aug

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

3. The Mountain Ave House by WanderLodges

Ashland

Joyce

AED 1,492 total

includes taxes & fees

9 Aug - 10 Aug

4. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

AED 1,548 total

includes taxes & fees

10 Aug - 11 Aug

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

5. Barclay Klum House by WanderLodges

Ashland

Melissa

AED 1,334 total

includes taxes & fees

9 Aug - 10 Aug

6. Chateau Herbe ~ Oberon Suite w/ Kitchen

Ashland

Larry D.

AED 925 total

includes taxes & fees

9 Aug - 10 Aug

7. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

Suzanne

AED 1,184 total

includes taxes & fees

25 Aug - 26 Aug

8. East Main Downtown Bungalow

Historic Railroad District

Hope S.

AED 801 total

includes taxes & fees

31 Aug - 1 Sep

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.

AED 925 total

includes taxes & fees

9 Aug - 10 Aug

10. Hanna's House by WanderLodges

Historic Railroad District

David

AED 965 total

includes taxes & fees

10 Aug - 11 Aug

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

Historic Downtown District

Virginia I.

AED 2,271 total

includes taxes & fees

27 Aug - 28 Aug

12. Quaint Downtown Ashland Studio- pet friendly!

Ashland

Ralph

AED 968 total

includes taxes & fees

18 Aug - 19 Aug

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

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

Siskiyou-Hargadine Historic District

Karen G.

AED 925 total

includes taxes & fees

24 Aug - 25 Aug

14. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

AED 1,057 total

includes taxes & fees

17 Aug - 18 Aug

15. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

AED 954 total

includes taxes & fees

25 Aug - 26 Aug

Coffee/tea maker, fridge, microwave, oven

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

Ashland

Matthew

AED 1,901 total

includes taxes & fees

10 Aug - 11 Aug

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

AED 1,297 total

includes taxes & fees

3 Sep - 4 Sep

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

Ashland

Casey K.

AED 1,586 total

includes taxes & fees

9 Aug - 10 Aug

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

19. The Matriarch| Suite 3 | Pet friendly

Historic Railroad District

Daniel

AED 921 total

includes taxes & fees

24 Aug - 25 Aug

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

Historic Railroad District

Jim L.

AED 1,108 total

includes taxes & fees

10 Aug - 11 Aug

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Top Ashland Hotel Reviews

Comfort Inn & Suites Ashland

10/10 Excellent

"I neglected to say no stairs and our room was downstairs which was somewhat difficult with a dog and I’m old."

Callahan's Mountain Lodge

10/10 Excellent

"We stayed here to be within 2 miles of our daughter and they were extremely dog friendly. Our room was nice and we especially enjoyed the small fenced patio that we sat on every day. Staff was nice and helpful. Coupons for breakfast were appreciated. Not sure restaurant staff is up to speed with recent changes. We went there during happy hour, but did not get happy hour prices on our food or drinks. We will definitely stay again when in the area. Thanks"

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

10/10 Excellent

"rooms very clean, nice to have a table and 2 chairs for eating in, loved the parking in front of our room, walkable, perfect location, very safe, nice pool and jacuzzi watching the deer roam the hillside across the street was a nice perk ... the breakfast was wonderful ... lots of healthy options ... the staff was on point and very responsive ... will be our place to stay when visiting Ashland and the Shakespeare festival"

Lithia Springs Resort

8/10 Good

"At our approach to the property, I was fairly underwhelmed. But, once you get past the gates, they do a fairly good job of reducing the fact that you are right off I5. The property was lovely and relaxing, and the rooms were fairly well maintained. Grows for the property would be: remove the jetted tubs in the rooms and replace with soaking tubs since the mineral water has corroded the metal jets to the point that our intake was no longer connected and appeared to be mended with a screw that kept falling out while using the tub, do not advertise a wine garden and wine flight that is only available 4 days a week, improve the ice machine so that it provides ice, and clean up the pool tiles a bit to make them look less dated."

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

How many vacation rentals are there in Ashland?

Choose from 107 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 Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Mount Ashland Ski Area 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.

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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

Comfort Inn & Suites Ashland

Best Western Windsor Inn

Callahan's Mountain Lodge

Ashland Hills Hotel & Suites

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

Ashland Springs Hotel

Lithia Springs Resort

Plaza Inn & Suites at Ashland Creek

Timbers INN and Suites

Frequently asked questions

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