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Our top choices for Ashland vacation homes

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 AED 473
AED 998 total
includes taxes & fees
7 Dec - 8 Dec
Barclay Klum House by WanderLodges

2. 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 AED 592
AED 1,192 total
includes taxes & fees
29 Nov - 30 Nov
The Mountain Ave House by WanderLodges

3. 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 AED 592
AED 1,342 total
includes taxes & fees
2 Dec - 3 Dec
Grandview of Ashland

4. 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 AED 374
AED 699 total
includes taxes & fees
10 Nov - 11 Nov
Hanna's House by WanderLodges

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 AED 657
AED 1,343 total
includes taxes & fees
30 Nov - 1 Dec
Savage Upon Siskiyou

6. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (56 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

7. 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 AED 448
AED 859 total
includes taxes & fees
10 Nov - 11 Nov
Hanna`s House | Downtown Retreat, Steps to OSF

8. Ashland Cottage | Walk to Downtown & Coffee

Ashland Cottage | Walk to Downtown & Coffee
Historic Railroad District
The price is AED 359
AED 830 total
includes taxes & fees
11 Nov - 12 Nov
Ashland Cottage | Walk to Downtown & Coffee

9. 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 AED 448
AED 772 total
includes taxes & fees
6 Dec - 7 Dec
Whimsy on B | The Studio

10. Swank Suites | King with Lux Tub

Swank Suites | King with Lux Tub
Historic Railroad District
Swank Suites | King with Lux Tub

11. 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

12. 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 AED 720
AED 864 total
includes taxes & fees
6 Dec - 7 Dec
Moody Ashland Escape: Luxe Suite, Copper Tub

13. Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Lovely location, close to downtown Ashland, but felt remote and quiet. Easy access to gorgeous bike\running path. Spacious apartment, cozy beds and nice bedding. Lots of parking, Host was easy to contact and addressed a minor maintenance issue quickly. Access to the Chateau with coffee bar and seating was a great extra. This is a great find!"
United States
Denise J.
Chateau Herb ~ Miranda Carriage House Apt

14. 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!

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!

16. 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 AED 572
AED 1,057 total
includes taxes & fees
6 Dec - 7 Dec
Whimsy on B | 2BR Steps to Downtown

17. 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, (85 reviews)
"We had a great time in a welcoming home"
United States
Deb B.
The price is AED 645
AED 1,669 total
includes taxes & fees
8 Nov - 9 Nov
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

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

19. Savage Upon Siskiyou | Prime OSF Location

Savage Upon Siskiyou | Prime OSF Location
Siskiyou-Hargadine Historic District
9.6 out of 10, Exceptional, (7 reviews)
"We loved the charm and character of this historic home! Very beautifully updated inside, my mother and daughter and I enjoyed a fun weekend in Ashland. The home was within a nice walking distance of downtown, perfect for shopping, eating out and theater going. We will definitely look to stay here again!"
United States
Jill A.
The price is AED 613
AED 1,343 total
includes taxes & fees
30 Nov - 1 Dec
Savage Upon Siskiyou | Prime OSF Location

20. Artisan 2-bedroom house in tranquil Ashland perfect for your getaway

Artisan 2-bedroom house in tranquil Ashland perfect for your getaway
Ashland
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