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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Ashland holiday homes

Sun deck

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 £306
includes taxes & fees
29 Jun - 30 Jun
Grandview of Ashland
Property grounds

The Red Dragon House

The Red Dragon House
Ashland
10.0 out of 10, Exceptional, (113 reviews)
"Fun place, great theme, easy place to stay!"
United States
Garrett P.
The price is £158
includes taxes & fees
13 Jul - 14 Jul
The Red Dragon House
Outdoor dining

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 £382
includes taxes & fees
29 Jun - 30 Jun
Hot tub | Sauna |Firepit |Sleeps 6!
Exterior

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 £192
includes taxes & fees
29 Jun - 30 Jun
Chateau Herb ~ Miranda Carriage House Apt
Exterior

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 £171
includes taxes & fees
5 Jul - 6 Jul
Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Dining

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
9.4 out of 10, Exceptional, (9 reviews)
"Super nice place and great host what a gem"
United States
Robert
The price is £258
includes taxes & fees
15 Jul - 16 Jul
Gorgeous Lakeside BarnHOUSE + SAUNA!
Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is £339
includes taxes & fees
6 Jul - 7 Jul
Savage Upon Siskiyou
Interior detail

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
The price is £235
includes taxes & fees
28 Jul - 29 Jul
Hanna's House by WanderLodges
Smart TV

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.
The price is £283
includes taxes & fees
28 Jul - 29 Jul
Hanna`s House | Downtown Retreat, Steps to OSF
Smart TV

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 £163
includes taxes & fees
29 Jun - 30 Jun
East Main Downtown Bungalow
Exterior

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 £206
includes taxes & fees
27 Jul - 28 Jul
Cabin #4 at Hyatt Lake Resort
Fridge, microwave, oven, stovetop

Quiet and peaceful cottage close to downtown

Quiet and peaceful cottage close to downtown
Siskiyou-Hargadine Historic District
9.8 out of 10, Exceptional, (67 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.
The price is £251
includes taxes & fees
6 Jul - 7 Jul
Quiet and peaceful cottage close to downtown
Fridge, microwave, oven, stovetop

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, (68 reviews)
"Great location and wonderful hot tub!"
United States
Ruth R.
The price is £403
includes taxes & fees
13 Jul - 14 Jul
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Smart TV

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 £382
includes taxes & fees
3 Jul - 4 Jul
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Luxury House, 2 Bedrooms, Bathtub, Garden Area | 2 bedrooms, laptop workspace, iron/ironing board, free WiFi

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 £324
includes taxes & fees
3 Jul - 4 Jul
Barclay Klum House by WanderLodges
1 bedroom, iron/ironing board, WiFi, bed sheets

Swank Suites- Top Floor + Private Patio

Swank Suites- Top Floor + Private Patio
Historic Railroad District
10.0 out of 10, Exceptional, (2 reviews)
"What a great property! We loved the walkable location, we loved the suite and room amenities, we loved the shared outdoor areas, and we loved the staff hospitality. no notes! We'll definitely stay here again when in Ashland."
United States
Timothy C.
The price is £156
includes taxes & fees
28 Jul - 29 Jul
Swank Suites- Top Floor + Private Patio
Exterior

Cabin #5 at Hyatt Lake Resort

Cabin #5 at Hyatt Lake Resort
Jackson County
The price is £219
includes taxes & fees
27 Jul - 28 Jul
Cabin #5 at Hyatt Lake Resort
Property grounds

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.
The price is £317
includes taxes & fees
29 Jun - 30 Jun
Charming house two blocks from downtown Ashland
Exterior

Whimsy on B | The Studio

Whimsy on B | The Studio
Historic Railroad District
The price is £195
includes taxes & fees
2 Jul - 3 Jul
Whimsy on B | The Studio
Grand House | Living area | 65-inch TV with digital channels, streaming services

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 £333
includes taxes & fees
26 Jul - 27 Jul
The Mountain Ave House by WanderLodges
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

10/10 Excellent
"Wonder hotel! Very clean and charming-perfect accommodations for our visit to the Oregon Shakespeare Festival. Only a 7 minutes drive to the theaters. We loved the hot breakfast, pool, and hot tub. We will absolutely stay here again."
Angela 1-night trip
Posted 1 hour ago
Best Western Windsor Inn

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
367
Accommodation
291 Holiday Homes
Lowest Price
£156
Highest Price
£403