Ashland vacation rentals

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Best Ashland vacation rentals

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$88 - $506$506 - $924$924 - $1,342$1,342 - $1,760$1,760+ per night

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Free cancellationFree breakfastFree parkingFree internet

Most recommended vacation rentals in Ashland

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Callahan's Mountain Lodge - Ashland - Living room
Callahan's Mountain Lodge
Ashland, OR
8.1Very good(93)
Free Wi-Fi
Pet friendly
$156+
Check availability
Grandview of Ashland - Ashland - Balcony
Grandview of Ashland
Ashland, OR
10Wonderful(3)
Parking
Free Wi-Fi
$450+
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Redtail Inn - 3 Suites Sleeps Up To 12 - Ashland - Balcony
Redtail Inn - 3 Suites Sleeps Up To 12
Ashland, OR
9.9Wonderful(6)
Free Wi-Fi
Pet friendly
$240+
Check availability
Hanna's House by WanderLodges - Ashland - Bedroom
Hanna's House by WanderLodges
Ashland, OR
9.9Wonderful(17)
Parking
Free Wi-Fi
$271+
Check availability
Ashland Cabin on 170 Acres with Mtn Views and Sauna! - Ashland - Living room
Ashland Cabin on 170 Acres with Mtn Views and Sauna!
Ashland, OR
8.8Very good(15)
Free Wi-Fi
$222+
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East Main Downtown Bungalow - Ashland - Bedroom
East Main Downtown Bungalow
Ashland, OR
9.1Wonderful(27)
$259+
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Swank House on Main St in Ashland - Ashland - Bedroom
Swank House on Main St in Ashland
Ashland, OR
10Wonderful(6)
Parking
Free Wi-Fi
$581+
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The Mountain House by WanderLodges - Ashland - Kitchen
The Mountain House by WanderLodges
Ashland, OR
9.4Wonderful(29)
Parking
Free Wi-Fi
$474+
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Downtown Ashland House - Walk to Plaza and OSF! - Ashland - Living room
Downtown Ashland House - Walk to Plaza and OSF!
Ashland, OR
9.6Wonderful(11)
Free Wi-Fi
$393+
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Florence Room at Chateau Herbe - Ashland - Living room
Florence Room at Chateau Herbe
Ashland, OR
10Wonderful(6)
$152+
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Chateau Herbe ~ Vienna Room - Ashland - Living room
Chateau Herbe ~ Vienna Room
Ashland, OR
10Wonderful(4)
$144+
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The Dogwood Suite at Tudor House Vacation Rentals - Ashland - Bedroom
The Dogwood Suite at Tudor House Vacation Rentals
Ashland, OR
9.6Wonderful(20)
Free Wi-Fi
$194+
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1907 Charmer, Perfect Downtown Location, So Clean! - Ashland - Living room
1907 Charmer, Perfect Downtown Location, So Clean!
Ashland, OR
9.4Wonderful(20)
$473+
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Charming well appointed Cottage in Ashland ( 800 + sq. ft. ) - Ashland - Living room
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Ashland, OR
10Wonderful(11)
Free Wi-Fi
$179+
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Second Street Cottages - Ashland
Second Street Cottages
Ashland, OR
9.6Wonderful(170)
Parking
Free Wi-Fi
$193+
Check availability
Mahar Homes - Plaza North on First - Ashland
Mahar Homes - Plaza North on First
Ashland, OR
9.8Wonderful(4)
Parking
Free Wi-Fi
$532+
Check availability
Booking Insights

KAYAK’s insights for vacation rentals in Ashland

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Ashland with confidence.

What is the cheapest day of the week to book a vacation rental in Ashland?

Sunday offers the lowest rates in Ashland, with an average nightly price of $134. The highest prices are found on Saturday, with average rates at $365.
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
December
$190
$339
Cheapest month to stay with an average 79% drop in price.
Most expensive month to stay with an average 85% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Ashland vacation rental deals

  • Pet friendly is the most popular vacation rental property amenity in Ashland
  • Vacation rentals in Ashland are around 31% more expensive than hotels on average. Search here to compare prices for all accommodation types in Ashland.
  • The best vacation rental properties in Ashland are Mt Ashland Homestead, Ashland 10m., 40 acres ridgetop old forest, right by PCT (10.0, 47 reviews), Hot Tub & Seasonal Pool -Sleeps 10- 4 min to OSF (9.9, 28), and The Dogwood Suite at Tudor House Vacation Rentals (9.6, 20), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Ashland with the most affordable vacation rental properties (3 properties with an average price of $160 per night). High Street Cottage Artists' Garden Cottage Clean & Beautiful, Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3, and Charming 2-bedroom Victorian Gem - Across Beautiful Lithia Park & Ashland Plaza are the most popular rental properties in Downtown.
  • If you’re looking for a cheap vacation rental in Ashland, you should consider visiting during the low season. The cheapest vacation homes in Ashland can be found in January and March.
  • The cheapest night for renting a vacation home in Ashland is Sunday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Ashland for 5 days.

FAQs when booking a vacation home in Ashland

  • How much is a vacation rental for a week in Ashland?

    The average price for a weekly Ashland vacation rental found by KAYAK users in the last 2 weeks is $940.

  • How much is a vacation rental for a month in Ashland?

    The average price for a monthly Ashland vacation rental found by KAYAK users in the last 2 weeks is $4,028.

  • What types of vacation rentals are available in Ashland?

    There are loads of different property types that you can make your vacation home in Ashland. You’ll find agritourism, apartments, bungalows, cabins, caravans, castles, chalets, cottages, houses, homestays, lodges, ranches and safari/tentalows.

  • What are some of the most-loved vacation rentals available in Ashland?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Callahan's Mountain Lodge.

  • Are there any pet-friendly vacation rentals in Ashland?

    There are a number of dog and pet-friendly Ashland vacation rentals, with around 2% allowing you to bring your pet along with you.

  • How much is a vacation rental in Ashland for tonight?

    In the last 72 hours, users have found Ashland vacation rentals for tonight for as low as $253. Search here for similar prices

  • How can I find vacation rentals near me in Ashland?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Ashland?

Our map will help you find the perfect place to stay in Ashland by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Ashland

Not what you’re looking for? Find thousands of other hotels, flight deals, car rentals and package deals with KAYAK.