Ashland, OR Vacation Homes from AED 848

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Our top choices for Ashland vacation homes

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

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.

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

AED 1,413 total

includes taxes & fees

7 Oct - 8 Oct

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

4. Hanna's House by WanderLodges

Historic Railroad District

David

AED 979 total

includes taxes & fees

2 Nov - 3 Nov

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

5. Grandview of Ashland

Ashland

Sonja

AED 1,504 total

includes taxes & fees

14 Oct - 15 Oct

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

6. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

AED 2,961 total

includes taxes & fees

31 Oct - 1 Nov

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

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

Historic Railroad District

Jim L.

A two-story house with a porch, a wooden fence, and a paved driveway.

8. Downtown Ashland House - Walk to Plaza and OSF!

Ashland

Jeff C.

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.

A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

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

Ashland

Casey K.

A cozy bedroom with a bed, a chair, a table, and a lamp.

11. Swank Suites | Step Free King - Pet Friendly

Historic Railroad District

Jessie M.

AED 848 total

includes taxes & fees

5 Oct - 6 Oct

A garden with a white fence, green hedges, and purple flowering trees.

12. Whimsy on B | The Studio

Historic Railroad District

Christy G.

A kitchen with white cabinets, a refrigerator, a stove, a microwave, and a sink.

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

Ashland

Matthew

AED 1,759 total

includes taxes & fees

4 Oct - 5 Oct

A kitchen with granite countertops, dark cabinetry, and a refrigerator.

14. Quiet and peaceful cottage close to downtown

Siskiyou-Hargadine Historic District

Sue P.

A bedroom with a large bed, a chandelier, a desk, a chair, and a window with curtains.

15. Moody Ashland Escape: Luxe Suite, Copper Tub

Historic Railroad District

Jon W.

A hallway with a blue wall, a framed welcome sign, a round mirror, and a table.

16. The Ashland Social | Main House

Ashland

Paul B.

AED 2,151 total

includes taxes & fees

27 Oct - 28 Oct

17. Whimsy on B | 2BR Steps to Downtown

Historic Railroad District

A stone bridge over a stream with autumn leaves, surrounded by trees and a stone wall.

18. Charming house two blocks from downtown Ashland

Historic Railroad District

Julia W.

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

19. Hot tub | Sauna |Firepit |Sleeps 6!

Ashland

Heather K.

A two-story house with a blue front door, number 485, surrounded by well-maintained lawns and flowering trees.

20. The Ashland Social | Entire Estate

Ashland

Donna M.

AED 2,649 total

includes taxes & fees

19 Oct - 20 Oct

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Top Ashland Hotel Reviews

Relax Inn At Ashland

10/10 Excellent

"Reasonable prices, total cleanness, responsive staff."

Callahan's Mountain Lodge

10/10 Excellent

"The new smaller portion menu is a plus and minus. Less food, same price. No add one is a big minus. I miss Shawn, the bartender, he gave it a step up..I miss the breakfast included, the new management does not do any bonues to people staying over night. We were on a time crunch and could not do a full service breakfast plus costs. The al a catre or grab and go way one of our reasons for using Callahans as our stop over. Our room was okish. I don't like the soap/shampoo/conditioner dispensers. Since 2 of the 3 were missing. Our room had a broken lock, so I could not get into my room with the key card. The new management needs to upgrade the locks on all doors, take care of guests and make sure all of the amenities are available. We talked to staff, they are happy with the new management, they are taken care of, in return, the guests are suffering. We've stayed her many times. We see good and bad with the new management. Usually I would give a 5 star review, I think with our current experience, it's maybe a 3+ish. We drive to pnw 3-5 times a year. Next time we might power through to a better location with better amenities, for the same price. I'm sad to leave this honest review, because we have always loved Callahans. We've referred Callahans. This last trip was sub par. All of the staff are wonderful, I fully think this is a management issue. Not a staff issue. On a positive side note, Sunshine, the server is a ray of sunshine. Thank you"

Lithia Springs Resort

10/10 Excellent

"Excellent stay at a beautiful property! The room was large and included a soaking tub with their famous mineral water, a sitting room, and a kitchenette. The property offers complimentary bicycles and laundry services, as well as afternoon tea with cookies from 3-5. I would definitely stay here again!"

Ashland Motel - Oregon

8/10 Good

"The room itself was cute and clean. The outside and the AC unit were a little dated but worked well. I did really miss having an ice machine but it was clearly stated that was not an offered amenity so it was not a surprise. The staff was wonderful and the description was informative and accurate. A great overall experience."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland vacation homes

1. Barclay Klum House by WanderLodges

2. East Main Downtown Bungalow

3. The Mountain Ave House by WanderLodges

4. Hanna's House by WanderLodges

5. Grandview of Ashland

6. Savage Upon Siskiyou

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

8. Downtown Ashland House - Walk to Plaza and OSF!

9. Chateau Herb ~ Miranda Carriage House Apt

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

11. Swank Suites | Step Free King - Pet Friendly

12. Whimsy on B | The Studio

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

14. Quiet and peaceful cottage close to downtown

15. Moody Ashland Escape: Luxe Suite, Copper Tub

16. The Ashland Social | Main House

17. Whimsy on B | 2BR Steps to Downtown

18. Charming house two blocks from downtown Ashland

19. Hot tub | Sauna |Firepit |Sleeps 6!

20. The Ashland Social | Entire Estate

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Relax Inn At Ashland

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

Callahan's Mountain Lodge

Cedarwood Inn of Ashland

Comfort Inn & Suites Ashland

Lithia Springs Resort

Ashland Motel - Oregon

Prospero's Flagship Inn

Ashland Hills Hotel & Suites

Search Vacation Homes in Ashland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland vacation homes

1. Barclay Klum House by WanderLodges

2. East Main Downtown Bungalow

3. The Mountain Ave House by WanderLodges

4. Hanna's House by WanderLodges

5. Grandview of Ashland

6. Savage Upon Siskiyou

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

8. Downtown Ashland House - Walk to Plaza and OSF!

9. Chateau Herb ~ Miranda Carriage House Apt

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

11. Swank Suites | Step Free King - Pet Friendly

12. Whimsy on B | The Studio

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

14. Quiet and peaceful cottage close to downtown

15. Moody Ashland Escape: Luxe Suite, Copper Tub

16. The Ashland Social | Main House

17. Whimsy on B | 2BR Steps to Downtown

18. Charming house two blocks from downtown Ashland

19. Hot tub | Sauna |Firepit |Sleeps 6!

20. The Ashland Social | Entire Estate

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Relax Inn At Ashland