Ashland, OR Vacation Homes from AED 785

A deer on a road with vegetation on the sides.

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Our top choices for Ashland vacation homes

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

1. Grandview of Ashland

Ashland

Sonja

AED 1,504 total

includes taxes & fees

14 Oct - 15 Oct

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

2. Barclay Klum House by WanderLodges

Ashland

Melissa

AED 1,042 total

includes taxes & fees

5 Oct - 6 Oct

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

3. Hanna's House by WanderLodges

Historic Railroad District

David

AED 930 total

includes taxes & fees

3 Nov - 4 Nov

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

4. The Mountain Ave House by WanderLodges

Ashland

Joyce

AED 1,384 total

includes taxes & fees

3 Nov - 4 Nov

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

5. East Main Downtown Bungalow

Historic Railroad District

Amy R.

AED 785 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 1,548 total

includes taxes & fees

6 Oct - 7 Oct

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 residential backyard with a wooden deck, outdoor seating, and umbrellas.

8. Swank Suites | King with Lux Tub

Historic Railroad District

Susie P.

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

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

Ashland

Casey K.

AED 1,330 total

includes taxes & fees

3 Nov - 4 Nov

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

10. Whimsy on B | The Studio

Historic Railroad District

Christy G.

11. 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

4 Oct - 5 Oct

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

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

Ashland

Jeff C.

13. Whimsy on B | 2BR Steps to Downtown

Historic Railroad District

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

14. Moody Ashland Escape: Luxe Suite, Copper Tub

Historic Railroad District

Jon W.

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

15. Quiet and peaceful cottage close to downtown

Siskiyou-Hargadine Historic District

Sue P.

AED 1,216 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

Ashland

Heather K.

AED 1,759 total

includes taxes & fees

14 Oct - 15 Oct

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

19. The Ashland Social | Main House

Ashland

Paul B.

AED 2,156 total

includes taxes & fees

27 Oct - 28 Oct

A bedroom with a large bed, a wooden dresser, a desk with a lamp, and a mirror.

20. Artisan 2-bedroom house in tranquil Ashland perfect for your getaway

Ashland

AED 2,214 total

includes taxes & fees

18 Oct - 19 Oct

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Top Ashland Hotel Reviews

Prospero's Flagship Inn

10/10 Excellent

"Clean spacious room. Great location great price. Would stay again."

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"

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. Grandview of Ashland

2. Barclay Klum House by WanderLodges

3. Hanna's House by WanderLodges

4. The Mountain Ave House by WanderLodges

5. East Main Downtown Bungalow

6. Savage Upon Siskiyou

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

8. Swank Suites | King with Lux Tub

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

10. Whimsy on B | The Studio

11. Chateau Herb ~ Miranda Carriage House Apt

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

13. Whimsy on B | 2BR Steps to Downtown

14. Moody Ashland Escape: Luxe Suite, Copper Tub

15. Quiet and peaceful cottage close to downtown

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

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

18. Charming house two blocks from downtown Ashland

19. The Ashland Social | Main House

20. Artisan 2-bedroom house in tranquil Ashland perfect for your getaway

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Prospero's Flagship Inn

Relax Inn At Ashland

Stratford Inn

Lithia Springs Resort

Holiday Inn Express & Suites Ashland by IHG

Callahan's Mountain Lodge

Cedarwood Inn of Ashland

Ashland Motel - Oregon

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. Grandview of Ashland

2. Barclay Klum House by WanderLodges

3. Hanna's House by WanderLodges

4. The Mountain Ave House by WanderLodges

5. East Main Downtown Bungalow

6. Savage Upon Siskiyou

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

8. Swank Suites | King with Lux Tub

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

10. Whimsy on B | The Studio

11. Chateau Herb ~ Miranda Carriage House Apt

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

13. Whimsy on B | 2BR Steps to Downtown

14. Moody Ashland Escape: Luxe Suite, Copper Tub

15. Quiet and peaceful cottage close to downtown

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

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

18. Charming house two blocks from downtown Ashland

19. The Ashland Social | Main House

20. Artisan 2-bedroom house in tranquil Ashland perfect for your getaway

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Prospero's Flagship Inn