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Vacation rentals in Ashland

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Travel insights for holiday rentals in Ashland

Use these up-to-date, data-driven insights about booking a holiday rental in Ashland including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Ashland?

The cheapest month to book a vacation rental in Ashland is September ($81). Conversely, the most expensive month to stay in Ashland is October ($764).

What is the cheapest day to stay in a vacation rental in Ashland?

The cheapest day to stay in Ashland is Wednesday ($121). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $314.
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Cheapest holiday rentals in Ashland, Oregon

Discover affordable stays in Ashland that provide a quality experience without breaking the bank. Hotels in Ashland can be found for as low as $121 per night. There is currently one property in Ashland that can be booked for this price. Callahan's Lodge and Restaurant is one of the hotels that can be booked for the lowest price in Ashland. Price data was last updated on 15 June 2025
Out of the vacation rentals in Ashland we've come across, these properties are priced the lowest. As prices can vary by date, change the dates if you're flexible to compare rates.
Show all 269 holiday rentals
Callahan's Lodge and Restaurant
Callahan's Lodge and Restaurant

Callahan's Lodge and Restaurant

Ashland, OR, United States
16.1 km from city centre
$121
Avg. per night
View Deal

Other accommodations in Ashland

Find the perfect holiday rental for your stay in Ashland. There are 269 hotels in Ashland and price data was last updated on 15 June 2025. The average price for a hotel in Ashland is $225/night.
Show all 269 stays
Country Willows Inn
Country Willows Inn

Country Willows Inn

1313 Clay St, Ashland, OR, United States
3.7 km from city centre
Air conditioning
$263
Avg. per night
View Deal
Arden Forest Inn
Arden Forest Inn

Arden Forest Inn

261 West Hersey Street, Ashland, OR, United States
1.2 km from city centre
Free Wi-Fi
Air conditioning
$161
Avg. per night
View Deal
Stratford Inn
Stratford Inn

Stratford Inn

555 Siskiyou Boulevard, Ashland, OR, United States
0.3 km from city centre
Pool
Free Wi-Fi
Parking
$123
Avg. per night
View Deal
Cedarwood Inn of Ashland
Cedarwood Inn of Ashland

Cedarwood Inn of Ashland

1801 Siskiyou Boulevard, Ashland, OR, United States
2.7 km from city centre
Pool
Free Wi-Fi
Parking
$100
Avg. per night
View Deal
Ashland Motel - Oregon
Ashland Motel - Oregon

Ashland Motel - Oregon

1145 Siskiyou Boulevard, Ashland, OR, United States
1.4 km from city centre
Free Wi-Fi
Parking
$93
Avg. per night
View Deal
Timbers Inn And Suites
Timbers Inn And Suites

Timbers Inn And Suites

1450 Ashland Street, Ashland, OR, United States
1.9 km from city centre
Free Wi-Fi
Parking
$75
Avg. per night
View Deal
Winchester Inn
Winchester Inn

Winchester Inn

35 South 2nd Street, Ashland, OR, United States
0.2 km from city centre
Free Wi-Fi
Air conditioning
$296
Avg. per night
View Deal

Where to stay in Ashland

Explore different neighbourhoods and areas within Ashland to find the perfect location for your stay. Map data was last updated on 15 June 2025.
Navigate to the areas in Ashland you plan to visit to find vacation rentals that are close by. You can find more information on a particular vacation rental within the map by clicking on its name.

Facts about staying in Ashland

Find useful tips and insights about staying in Ashland to help you make the most of your experience. FAQs were last updated on 15 June 2025.

  • How much does a holiday rental in Ashland cost?

    The average cost for a holiday rental in Ashland is $225/night. A good holiday rental deal in Ashland would be for $215/night or less. The cheapest rental deal found recently by our users was $23/night. If you’re flexible with your travel dates, then try to avoid booking October, the most expensive month of the year. Booking January is the cheapest month to book a holiday rental in Ashland.

  • Are there any Resort holiday rentals in Ashland?

    Yes, there are 3 Resort holiday rentals in Ashland. According to our data, Lithia Springs Resort is currently the most popular Resort rental in the city.

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