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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is ￥17,740
￥39,876 total
includes taxes & fees
Oct 26 - Oct 27
Barclay Klum House by WanderLodges
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

2. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is ￥25,099
￥54,048 total
includes taxes & fees
Oct 26 - Oct 27
Savage Upon Siskiyou
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

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is ￥18,450
￥32,640 total
includes taxes & fees
Nov 3 - Nov 4
Hanna's House by WanderLodges
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

4. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is ￥25,127
￥50,734 total
includes taxes & fees
Oct 26 - Oct 27
The Mountain Ave House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

5. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
The price is ￥30,327
￥62,439 total
includes taxes & fees
Nov 2 - Nov 3
Grandview of Ashland
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

6. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (55 reviews)
"The bungalow was great. Every room was comfortable and efficient for what we needed. The location is perfect...quiet yet easy walk to anywhere downtown. We would stay here again!!"
United States
Amy R.
East Main Downtown Bungalow
A bedroom with a large bed, a chandelier, a desk, a chair, and a window with curtains.

7. Moody Ashland Escape: Luxe Suite, Copper Tub

Moody Ashland Escape: Luxe Suite, Copper Tub
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Gorgeous decor, unbeatable location, and gracious hosts have thought of every need."
United States
Nancy
Moody Ashland Escape: Luxe Suite, Copper Tub
A classical-style fountain with statues in a landscaped garden area, surrounded by a large white building with a steeply pitched roof and multiple windows.

8. Chateau Herb ~ Juliet Carriage House Studio

Chateau Herb ~ Juliet Carriage House Studio
Ashland
8.8 out of 10, Excellent, (9 reviews)
"Beautiful property, room very clean and well-appointed. "
United States
Anonymous traveler
The price is ￥25,249
￥36,286 total
includes taxes & fees
Oct 30 - Oct 31
Chateau Herb ~ Juliet Carriage House Studio
A shower with a handheld showerhead and a wall-mounted faucet.

9. Swank Boutique Suites | King Suite | DT Ashland

Swank Boutique Suites | King Suite | DT Ashland
Historic Railroad District
10.0 out of 10, Exceptional, (9 reviews)
"Host was very responsive. The bed was like sleeping on a cloud."
United States
Bobby W.
The price is ￥29,935
￥36,873 total
includes taxes & fees
Oct 30 - Oct 31
Swank Boutique Suites | King Suite | DT Ashland
A modern kitchen with a central island, bar stools, and a built-in oven.

10. Ashland Cottage | Walk to Downtown & Coffee

Ashland Cottage | Walk to Downtown & Coffee
Historic Railroad District
The price is ￥13,667
￥35,354 total
includes taxes & fees
Oct 26 - Oct 27
Ashland Cottage | Walk to Downtown & Coffee
A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

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

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
10.0 out of 10, Exceptional, (171 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
The price is ￥19,844
￥39,387 total
includes taxes & fees
Nov 2 - Nov 3
Hanna`s House | Downtown Retreat, Steps to OSF
A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

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

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Ashland
10.0 out of 10, Exceptional, (6 reviews)
"Lovely stay in a nicely restored historic home. We were very comfortable and the location is great in central Ashland."
United States
Casey K.
The price is ￥18,809
￥47,119 total
includes taxes & fees
Oct 25 - Oct 26
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
A garden with a white fence, green hedges, and purple flowering trees.

13. Whimsy on B | The Studio

Whimsy on B | The Studio
Historic Railroad District
10.0 out of 10, Exceptional, (1 review)
"This is a great place to stay. Walkable to the theaters and many restaurants. Thank you!"
United States
Christy G.
The price is ￥17,068
￥31,992 total
includes taxes & fees
Nov 1 - Nov 2
Whimsy on B | The Studio
A garden with a white fence, green hedges, and purple flowering trees.

14. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
The price is ￥22,260
￥44,432 total
includes taxes & fees
Oct 25 - Oct 26
Whimsy on B | 2BR Steps to Downtown
A two-story house with a porch, a wooden fence, and a paved driveway.

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

Downtown Ashland House - Walk to Plaza and OSF!
Ashland
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay and so close to shops and restaurants. "
United States
Jeff C.
The price is ￥23,196
￥60,835 total
includes taxes & fees
Oct 26 - Oct 27
Downtown Ashland House - Walk to Plaza and OSF!
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

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Ashland
9.8 out of 10, Exceptional, (83 reviews)
"We had a great time in a welcoming home"
United States
Deb B.
The price is ￥27,506
￥75,056 total
includes taxes & fees
Oct 25 - Oct 26
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
A kitchen with granite countertops, dark cabinetry, and a refrigerator.

17. Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (72 reviews)
"Beautiful home, small but well stocked kitchen area. Fold-out sofa bed was ok for 1 night. The upstairs suite was very nice, really pretty furnishings, kind of steep stairs. Host was easy to reach abd very helpful."
United States
Patti M.
Quiet and peaceful cottage close to downtown
A single-story house with a covered porch, a small garden area with various plants, and a gravel driveway.

18. Charming house two blocks from downtown Ashland

Charming house two blocks from downtown Ashland
Historic Railroad District
9.6 out of 10, Exceptional, (12 reviews)
"This is our favorite spot to stay in Ashland! The location is perfect for walking downtown to the shops and theaters, shopping at the local co-op, or just enjoying a sunny breakfast on the deck."
United States
Julia W.
The price is ￥35,264
￥62,913 total
includes taxes & fees
Oct 29 - Oct 30
Charming house two blocks from downtown Ashland
A two-story house with a porch, a small garden, and a metal fence.

19. Savage Upon Siskiyou | Prime OSF Location

Savage Upon Siskiyou | Prime OSF Location
Siskiyou-Hargadine Historic District
9.0 out of 10, Wonderful, (4 reviews)
"Great location. Easy to walk everywhere. Thanks for great stay"
United States
Anonymous traveler
The price is ￥23,964
￥60,274 total
includes taxes & fees
Oct 26 - Oct 27
Savage Upon Siskiyou | Prime OSF Location
A deck with a fire pit, seating, and a view of the mountains.

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

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely stunning property in the hills of Ashland!"
United States
Heather K.
Hot tub | Sauna |Firepit |Sleeps 6!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Lithia Springs Resort

Lithia Springs Resort

8/10 Good
"We didn’t use the pool or hot tub but we did soak in the tub inside our room. We enjoyed the breakfast and feeding the koi fish. Our couples massage was wonderful. The carpets looked dated and stained in the dining area. The other thing we noticed was that the employee’s weren’t smiling, which kinda bothered me. We would go back though. The room was comfortable but the clarity on the tv was pretty bad."
Victoria 2-night trip
Posted 14 hours ago
Lithia Springs Resort

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews
420
Accommodation
276 Vacation Homes
Lowest Price
￥31,992
Highest Price
￥75,056