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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Ashland vacation homes

Luxury House, 2 Bedrooms, Bathtub, Garden Area

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is ￥23,344
￥45,794 total
includes taxes & fees
Sep 14 - Sep 15
Barclay Klum House by WanderLodges
Living area

2. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (53 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.
The price is ￥15,976
￥34,888 total
includes taxes & fees
Sep 9 - Sep 10
East Main Downtown Bungalow
Grand House | Living area

3. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is ￥33,592
￥59,799 total
includes taxes & fees
Sep 12 - Sep 13
The Mountain Ave House by WanderLodges
Sundeck

4. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 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 ￥31,178
￥62,781 total
includes taxes & fees
Sep 13 - Sep 14
Grandview of Ashland
Interior

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 ￥35,300
￥64,969 total
includes taxes & fees
Sep 11 - Sep 12
Savage Upon Siskiyou
Interior detail

6. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (4 reviews)
"Next visit to the OSF no question we’ll stay here if available. Short walking distance to everything in downtown Ashland, yet quiet and private."
United States
David
The price is ￥35,479
￥51,581 total
includes taxes & fees
Sep 27 - Sep 28
Hanna's House by WanderLodges
Private kitchen

7. 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, (77 reviews)
"Nice spot close to downtown and OSF."
United States
Matthew
The price is ￥27,053
￥73,821 total
includes taxes & fees
Sep 10 - Sep 11
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Exterior

8. Chateau Herb ~ Juliet Carriage House Studio

Chateau Herb ~ Juliet Carriage House Studio
Ashland
8.8 out of 10, Excellent, (8 reviews)
"Beautiful property, room very clean and well-appointed. "
United States
Anonymous traveler
Chateau Herb ~ Juliet Carriage House Studio
Exterior

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

Downtown Ashland House - Walk to Plaza and OSF!
Ashland
9.8 out of 10, Exceptional, (46 reviews)
"Great place to stay and so close to shops and restaurants. "
United States
Jeff C.
The price is ￥24,818
￥62,506 total
includes taxes & fees
Sep 13 - Sep 14
Downtown Ashland House - Walk to Plaza and OSF!
Exterior

10. Whimsy on B | The Studio

Whimsy on B | The Studio
Historic Railroad District
Whimsy on B | The Studio
Outdoor dining

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.
Swank Suites | King with Lux Tub
Private kitchen

12. Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (69 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
Living area

13. 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, (5 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 ￥25,265
￥55,802 total
includes taxes & fees
Sep 14 - Sep 15
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Living area

14. 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 ￥33,743
￥57,795 total
includes taxes & fees
Sep 27 - Sep 28
Hanna`s House | Downtown Retreat, Steps to OSF
Property grounds

15. 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
Interior

16. The Ashland Social | Main House

The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (36 reviews)
"Home is beautiful and well-located in Ashland. Amenities were great, and having three en-suite bedrooms was perfect. Host communicated well and often to ensure trouble-free experience. Fully equipped kitchen ideal for anyone to enjoy.We highly recommend this property!"
United States
Paul B.
The Ashland Social | Main House
Exterior detail

17. Come Stroll-inn in Downtown Ashland

Come Stroll-inn in Downtown Ashland
Historic Railroad District
The price is ￥34,684
￥69,784 total
includes taxes & fees
Sep 20 - Sep 21
Come Stroll-inn in Downtown Ashland
Outdoor dining

18. 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!
Room

19. 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
Exterior

20. Whimsy on B | 2BR Steps to Downtown

Whimsy on B | 2BR Steps to Downtown
Historic Railroad District
The price is ￥26,961
￥50,873 total
includes taxes & fees
Sep 20 - Sep 21
Whimsy on B | 2BR Steps to Downtown
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

Ashland Springs Hotel

Ashland Springs Hotel

8/10 Good
"Ashland Springs Hotel is the best-located hotel in Ashland for purposes of attending the Oregon Shakespeare Festival. Staff is uniformly helpful and the amenities (including modest breakfast for $5,) are great. Any issues are merely quibbles (e.g. breakfast offerings could be more diverse, coffee pot should be reliably restocked on mezzanine). Overall, great stay! Expensive, but worth it!"
David 5-night trip
Posted less than an hour ago
Ashland Springs Hotel

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews
463
Accommodation
273 Vacation Homes
Lowest Price
￥32,486
Highest Price
￥107,029