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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Ashland holiday rentals

A bedroom with a bed, a sofa, a desk, and a window with blinds.

1. Whimsy on B

Whimsy on B
3.0 star property
Historic Railroad District
The price is 2.343.562 ₫
4.234.750 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Whimsy on B
A wooden door with a small window above it, a porch with a wooden railing, and a green hose on the right side.

2. Whimsy On B 2br & Studio

Whimsy On B 2br & Studio
2.5 star property
Historic Railroad District
The price is 4.112.722 ₫
8.146.559 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Whimsy On B 2br & Studio
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 3.018.240 ₫
6.647.897 ₫ total
includes taxes & fees
9 Dec - 10 Dec
Barclay Klum House by WanderLodges
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

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 2.597.448 ₫
4.860.229 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Hanna's House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

5. 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 4.112.722 ₫
9.330.887 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Grandview of Ashland
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 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 4.263.343 ₫
8.994.887 ₫ total
includes taxes & fees
15 Nov - 16 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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Top Ashland Hotel Reviews

Green Springs Inn

Green Springs Inn

10/10 Excellent
"I stayed here 10 years ago and have always wanted to come back! Very comfortable room in a beautiful setting."
Lesley 1-night trip
Posted 13 hours ago
Green Springs Inn

Frequently asked questions

Can I find holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to ScienceWorks Hands-On Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theatre scene this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

How many holiday rentals are there in Ashland?

Choose from 106 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Oregon Cabaret Theatre are other places to visit while you're in town.

What are holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family getaway.