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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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

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 AU$374
includes taxes & fees
18 Oct - 19 Oct
Barclay Klum House by WanderLodges
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

2. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (5 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 AU$301
includes taxes & fees
19 Oct - 20 Oct
Hanna's House by WanderLodges
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

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

4. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is AU$607
includes taxes & fees
20 Oct - 21 Oct
Grandview of Ashland
A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

5. 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.
Hanna`s House | Downtown Retreat, Steps to OSF
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

6. 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 AU$535
includes taxes & fees
25 Oct - 26 Oct
The Mountain Ave 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.

7. 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 AU$609
includes taxes & fees
25 Oct - 26 Oct
Savage Upon Siskiyou
A garden with a white fence, green hedges, and purple flowering trees.

8. 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 AU$338
includes taxes & fees
8 Nov - 9 Nov
Whimsy on B | The Studio
An outdoor patio with wicker furniture, including two chairs and a table.

9. Ashland Cottage | Walk to Downtown & Coffee

Ashland Cottage | Walk to Downtown & Coffee
Historic Railroad District
Ashland Cottage | Walk to Downtown & Coffee
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

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.
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
A kitchen with a stainless steel sink, white cabinets, and a flat-screen TV mounted above the cabinets.

11. Swank Suites | King with Lux Tub

Swank Suites | King with Lux Tub
Historic Railroad District
9.4 out of 10, Exceptional, (3 reviews)
"This is definitely the place we will hope to stay next time! Great location, sweet cottage, and easy everything."
United States
Bridget A.
The price is AU$280
includes taxes & fees
16 Nov - 17 Nov
Swank Suites | King with Lux Tub
A garden with a white fence, green hedges, and purple flowering trees.

12. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
Whimsy on B | 2BR Steps to Downtown
Exterior

13. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"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."
United States
Cameron A.
Chateau Herb ~ Miranda Carriage House Apt
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

Moody Ashland Escape: Luxe Suite, Copper Tub
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"We really enjoyed our overnight stay. The place is centrally located, easy walking distance to downtown, and cozy. We loved the heated bathroom floors and the decor. Nice off street parking. Highly recommend. "
United States
Jon W.
Moody Ashland Escape: Luxe Suite, Copper Tub
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.
Downtown Ashland House - Walk to Plaza and OSF!
A kitchen with granite countertops, dark cabinetry, and a refrigerator.

16. 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)
"The property was very pleasant and clean... great directions to get to it, friendly host, sweet outdoor space, clean and welcoming. "
United States
Sue P.
Quiet and peaceful cottage close to downtown
A deck with a fire pit, seating, and a view of the mountains.

17. 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.
The price is AU$696
includes taxes & fees
20 Oct - 21 Oct
Hot tub | Sauna |Firepit |Sleeps 6!
A stone bridge over a stream with autumn leaves, surrounded by trees and a stone wall.

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.
Charming house two blocks from downtown Ashland
A kitchen with white cabinets, a refrigerator, a stove, a microwave, and a sink.

19. 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)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is AU$708
includes taxes & fees
19 Oct - 20 Oct
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
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

Artisan 2-bedroom house in tranquil Ashland perfect for your getaway
Ashland
The price is AU$872
includes taxes & fees
18 Oct - 19 Oct
Artisan 2-bedroom house in tranquil Ashland perfect for your getaway
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

Best Western Windsor Inn

Best Western Windsor Inn

8/10 Good
"Breakfast was nearly empty and not great- staff did not care. Older property, it was reasonably clean but out of date."
Ernest 2-night trip
Posted 1 hour ago
Best Western Windsor Inn

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
416
Accommodation
277 Holiday Homes
Lowest Price
AU$280
Highest Price
AU$872