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Our top choices for Ashland holiday homes

1. Whimsy on B

Whimsy on B
3.0 star property
Historic Railroad District
The price is £120
includes taxes & fees
14 Nov - 15 Nov
Whimsy on B

2. 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 £194
includes taxes & fees
17 Nov - 18 Nov
Barclay Klum House by WanderLodges

3. Whimsy On B 2br & Studio

Whimsy On B 2br & Studio
2.5 star property
Historic Railroad District
The price is £240
includes taxes & fees
16 Nov - 17 Nov
Whimsy On B 2br & Studio

4. 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 £275
includes taxes & fees
8 Dec - 9 Dec
Grandview of Ashland

5. 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 £255
includes taxes & fees
17 Nov - 18 Nov
Savage Upon Siskiyou

6. 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 £143
includes taxes & fees
16 Nov - 17 Nov
Hanna's House by WanderLodges

7. 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 £226
includes taxes & fees
15 Nov - 16 Nov
The Mountain Ave House by WanderLodges

8. 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 £151
includes taxes & fees
16 Nov - 17 Nov
Hanna`s House | Downtown Retreat, Steps to OSF

9. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (56 reviews)
"Fantastic spot, walkable to anything in downtown. Well-appointed, clean, easy. Definitely recommend."
United States
Melissa D.
The price is £157
includes taxes & fees
10 Dec - 11 Dec
East Main Downtown Bungalow

10. Ashland Cottage | Walk to Downtown & Coffee

Ashland Cottage | Walk to Downtown & Coffee
Historic Railroad District
The price is £157
includes taxes & fees
16 Nov - 17 Nov
Ashland Cottage | Walk to Downtown & Coffee

11. Park & Pillow - Bright 2BR Escape, Stroll to OSF Theaters & Town

Park & Pillow - Bright 2BR Escape, Stroll to OSF Theaters & Town
Ashland
The price is £167
includes taxes & fees
19 Nov - 20 Nov
Park & Pillow - Bright 2BR Escape, Stroll to OSF Theaters & Town

12. 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 £124
includes taxes & fees
10 Dec - 11 Dec
Swank Suites | King with Lux Tub

13. 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
The price is £177
includes taxes & fees
10 Dec - 11 Dec
Moody Ashland Escape: Luxe Suite, Copper Tub

14. 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 £265
includes taxes & fees
10 Dec - 11 Dec
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

15. 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 £305
includes taxes & fees
2 Dec - 3 Dec
Hot tub | Sauna |Firepit |Sleeps 6!

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

Downtown Ashland House - Walk to Plaza and OSF!
Ashland
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay and so close to shops and restaurants. "
United States
Jeff C.
Downtown Ashland House - Walk to Plaza and OSF!

17. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"The apartment was very cute, clean and comfortable. It was close to anything I needed to get to and also very secluded and peaceful."
United States
Dawn Y.
The price is £189
includes taxes & fees
14 Nov - 15 Nov
Chateau Herb ~ Miranda Carriage House Apt

18. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
8.0 out of 10, Very good, (1 review)
"Everything was very clean in this house. It is within a 7 minute walk of the theaters so made it VERY convenient for us - no hassle about where to park. The beds were great with plenty of pillows. I highly recommend this place."
United States
Mary Beth
The price is £222
includes taxes & fees
10 Dec - 11 Dec
Whimsy on B | 2BR Steps to Downtown

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, (87 reviews)
"We had a great time in a welcoming home"
United States
Deb B.
The price is £327
includes taxes & fees
15 Nov - 16 Nov
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

20. 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 £285
includes taxes & fees
10 Dec - 11 Dec
Charming house two blocks from downtown Ashland
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

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Ashland Holiday Homes information

Number of reviews
428
Accommodation
273 Holiday Homes
Lowest Price
£124
Highest Price
£327