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Find holiday rentals that suit your style

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Ashland holiday homes

A wooden door with a small window above it, a porch with a wooden railing, and a green hose on the right side.

1. Whimsy On B 2br & Studio

Whimsy On B 2br & Studio
2.5 star property
Historic Railroad District
The price is RM654
RM1,295 total
includes taxes & fees
15 Nov - 16 Nov
Whimsy On B 2br & Studio
A bedroom with a bed, a sofa, a desk, and a window with blinds.

2. Whimsy on B

Whimsy on B
3.0 star property
Historic Railroad District
The price is RM373
RM673 total
includes taxes & fees
15 Nov - 16 Nov
Whimsy on B
A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

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 RM479
RM1,054 total
includes taxes & fees
6 Dec - 7 Dec
Barclay Klum House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

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 RM654
RM1,484 total
includes taxes & fees
2 Dec - 3 Dec
Grandview of Ashland
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

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 RM371
RM726 total
includes taxes & fees
10 Nov - 11 Nov
Hanna's House by WanderLodges
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

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 price is RM566
RM1,220 total
includes taxes & fees
10 Nov - 11 Nov
The Mountain Ave House by WanderLodges
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

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
The price is RM678
RM1,430 total
includes taxes & fees
10 Nov - 11 Nov
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.
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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.

See all hotels in Ashland
A stone bridge over a calm stream with autumn leaves.