Ashland Vacation Homes

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Our top choices for Ashland holiday 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

HK$2,224 total

includes taxes & fees

7 Sept - 8 Sept

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

3. Grandview of Ashland

Ashland

Sonja

HK$3,209 total

includes taxes & fees

13 Sept - 14 Sept

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

4. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

HK$3,304 total

includes taxes & fees

7 Sept - 8 Sept

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

5. The Mountain Ave House by WanderLodges

Ashland

Joyce

HK$2,701 total

includes taxes & fees

7 Sept - 8 Sept

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

6. Hanna's House by WanderLodges

Historic Railroad District

David

HK$2,089 total

includes taxes & fees

20 Sept - 21 Sept

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.

HK$2,374 total

includes taxes & fees

10 Sept - 11 Sept

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.

A bedroom with a four-poster bed, a small kitchenette, and a wooden ceiling.

9. Swank Suites | King with Lux Tub

Historic Railroad District

Susie P.

HK$1,538 total

includes taxes & fees

7 Sept - 8 Sept

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

10. Whimsy on B | The Studio

Historic Railroad District

HK$1,725 total

includes taxes & fees

14 Sept - 15 Sept

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

11. Quiet and peaceful cottage close to downtown

Siskiyou-Hargadine Historic District

Sue P.

HK$2,596 total

includes taxes & fees

6 Sept - 7 Sept

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

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

Ashland

Matthew

HK$4,300 total

includes taxes & fees

29 Sept - 30 Sept

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

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

Ashland

Casey K.

HK$2,614 total

includes taxes & fees

7 Sept - 8 Sept

14. 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.

HK$2,363 total

includes taxes & fees

29 Sept - 30 Sept

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

15. The Ashland Social | Main House

Ashland

Paul B.

HK$4,455 total

includes taxes & fees

7 Sept - 8 Sept

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

16. Charming house two blocks from downtown Ashland

Historic Railroad District

Julia W.

HK$3,112 total

includes taxes & fees

3 Sept - 4 Sept

A residential property with a pathway leading to a house, surrounded by a wooden fence, and featuring a small patio area.

17. Come Stroll-inn in Downtown Ashland

Siskiyou-Hargadine Historic District

HK$3,549 total

includes taxes & fees

4 Sept - 5 Sept

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

18. Moody Ashland Escape: Luxe Suite, Copper Tub

Historic Railroad District

Jon W.

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

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

Ashland

Heather K.

20. Whimsy on B | 2BR Steps to Downtown

Historic Railroad District

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Top Ashland Hotel Reviews

Prospero's Flagship Inn

8/10 Good

":The video check-in is off putting. although the young woman was certainly pleasant, it depersonalizes the greeting. Not sure that's how I'd initiate a first impression. I can't imagine this remote system is more efficient. Is it a security issue? Is a new virus running amok?Are front office folks being assaulted at 4:00PM in Ashland? Also--we could have used a more user-friendly TV remote, or some user friendly instructions."

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."

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