Ashland Private Home Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Ashland holiday homes

1. Whimsy On B 2br & Studio

Whimsy On B 2br & Studio
2.5 star property
Historic Railroad District
The price is S$409
includes taxes & fees
15 Nov - 16 Nov
Whimsy On B 2br & Studio

2. Whimsy on B

Whimsy on B
3.0 star property
Historic Railroad District
The price is S$213
includes taxes & fees
15 Nov - 16 Nov
Whimsy on B

3. 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 S$328
includes taxes & fees
6 Dec - 7 Dec
Barclay Klum House by WanderLodges

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 S$467
includes taxes & fees
10 Dec - 11 Dec
Grandview of Ashland

5. 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 S$244
includes taxes & fees
22 Nov - 23 Nov
Hanna's House by WanderLodges

6. 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 Mountain Ave House by WanderLodges

7. 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
Savage Upon Siskiyou
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.

Learn more about Ashland

World-class Shakespeare performances unfold in outdoor theatres surrounded by mountain views from June through October. Lithia Park's trails wind along Ashland Creek, perfect for morning walks before browsing the city centre galleries and craft breweries.

A stone bridge over a calm stream with autumn leaves.