A resident black-tail deer walks the streets of Ashland, Oregon

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Our top choices for Ashland vacation homes

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Grandview of Ashland was a beautiful home!! It was super clean and the views of the valley were amazing. Our entire party had a wonderful time and would 100% stay there again. Highly recommend!"
United States
Paul
The price is AED 735
AED 1,488 total
includes taxes & fees
25 Jun - 26 Jun
Grandview of Ashland

Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Ashland
8.6 out of 10, Excellent, (4 reviews)
"Beautiful spot. Kind host."
United States
Lisa F.
The price is AED 714
AED 789 total
includes taxes & fees
18 Jun - 19 Jun
Owl Creek Cabin Mountain Getaway near Ashland, Oregon

The Red Dragon House

The Red Dragon House
Ashland
10.0 out of 10, Exceptional, (112 reviews)
"Fun place, great theme, easy place to stay!"
United States
Garrett P.
The price is AED 657
AED 753 total
includes taxes & fees
13 Jul - 14 Jul
The Red Dragon House

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
9.4 out of 10, Exceptional, (8 reviews)
"Super nice place and great host what a gem"
United States
Robert
Gorgeous Lakeside BarnHOUSE + SAUNA!

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is AED 435
AED 956 total
includes taxes & fees
21 Jun - 22 Jun
Barclay Klum House by WanderLodges

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (8 reviews)
"Perfect huge Chateau territory! Clean rooms) quiet territory. The hosts are always available. "
United States
Irina
The price is AED 812
AED 1,107 total
includes taxes & fees
28 Jun - 29 Jun
Chateau Herb ~ Miranda Carriage House Apt

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 AED 804
AED 1,809 total
includes taxes & fees
25 Jun - 26 Jun
Hot tub | Sauna |Firepit |Sleeps 6!

Cabin #4 at Hyatt Lake Resort

Cabin #4 at Hyatt Lake Resort
Jackson County
10.0 out of 10, Exceptional, (1 review)
"Everybody here has been so nice. This has been an amazing experience we will be back. "
United States
izak p.
The price is AED 672
AED 1,091 total
includes taxes & fees
29 Jun - 30 Jun
Cabin #4 at Hyatt Lake Resort

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is AED 797
AED 1,499 total
includes taxes & fees
22 Jun - 23 Jun
Savage Upon Siskiyou

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 AED 746
AED 1,364 total
includes taxes & fees
28 Jun - 29 Jun
The Mountain Ave House by WanderLodges

Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
Hanna's House by WanderLodges

Cabin #5 at Hyatt Lake Resort

Cabin #5 at Hyatt Lake Resort
Jackson County
The price is AED 731
AED 1,163 total
includes taxes & fees
13 Jul - 14 Jul
Cabin #5 at Hyatt Lake Resort

Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (66 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

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (49 reviews)
"Len provided me with an outdoor table and extra chairs so I could have dinner outside with my family because one had the flu. So wonderful to be able to socialize with everyone without risking getting the flu! House was very comfortable and well supplied. Close to downtown and hiking. Off street parking for one car. Thank you so much!!!"
United States
Judy
The price is AED 415
AED 868 total
includes taxes & fees
29 Jun - 30 Jun
East Main Downtown Bungalow

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 AED 481
AED 1,154 total
includes taxes & fees
21 Jun - 22 Jun
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

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
10.0 out of 10, Exceptional, (66 reviews)
"Great location and wonderful hot tub!"
United States
Ruth R.
The price is AED 948
AED 2,146 total
includes taxes & fees
8 Jul - 9 Jul
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Swank Boutique Suites | Double Shower

Swank Boutique Suites | Double Shower
Historic Railroad District
10.0 out of 10, Exceptional, (5 reviews)
"Great stay. Very little traffic noise from E Main St. Comfortable room and unique double shower. A "
United States
Brent S.
The price is AED 595
AED 745 total
includes taxes & fees
22 Jun - 23 Jun
Swank Boutique Suites | Double Shower

Charming house two blocks from downtown Ashland

Charming house two blocks from downtown Ashland
Historic Railroad District
9.6 out of 10, Exceptional, (11 reviews)
"Charming as can be and at the perfect location for all that Ashland has to offer. The neighborhood is quiet and friendly with lots to offer."
United States
Bill B.
Charming house two blocks from downtown Ashland

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, (170 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

The Ashland Social | Main House

The Ashland Social | Main House
Ashland
10.0 out of 10, Exceptional, (31 reviews)
"Gorgeous place! Especially enjoyed the pool and hot tub! Very comfy, quiet, and we loved the location. "
United States
Pretty W.
The Ashland Social | Main House
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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