Ashland vacation rentals

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Booking Insights
Recommended by KAYAK

Best Ashland vacation rentals

These are the best prices for May 12 - 13.
Game Room Fun! Medford Family Retreat - Medford - Patio
Game Room Fun! Medford Family Retreat
Medford, OR
10Wonderful(11)
House
$292+
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The Mountain House by WanderLodges - Ashland - Kitchen
The Mountain House by WanderLodges
Ashland, OR
9.3Wonderful(32)
House
$478+
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Barclay Klum House by WanderLodges - Ashland - Living room
Barclay Klum House by WanderLodges
Ashland, OR
9.4Wonderful(8)
Apartment
$310+
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Hanna's House by WanderLodges - Ashland - Bedroom
Hanna's House by WanderLodges
Ashland, OR
9.9Wonderful(19)
House
$397+
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European Style Straw Bale Retreat - Ashland - Bedroom
European Style Straw Bale Retreat
Ashland, OR
9.8Wonderful(12)
House
$312+
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Charming 2br Cottage Near Freeway-Cul-De - Medford - Kitchen
Charming 2br Cottage Near Freeway-Cul-De
Medford, OR
8.8Very good(20)
House
$212+
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Sunshine Studio - Private apt and yard (eco, solar) - Medford - Patio
Sunshine Studio - Private apt and yard (eco, solar)
Medford, OR
9.9Wonderful(61)
Apartment
$141+
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Grandview of Ashland - Ashland - Balcony
Grandview of Ashland
Ashland, OR
10Wonderful(3)
House
$720+
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Newly renovated studio with farm and mountain view’s! 5 minutes to Jacksonville. - Medford - Bedroom
Newly renovated studio with farm and mountain view’s! 5 minutes to Jacksonville.
Medford, OR
9.6Wonderful(17)
Apartment
$167+
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Downtown Mint - Medford - Living room
Downtown Mint
Medford, OR
9.8Wonderful(39)
Cottage
$238+
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Chic & cozy 1 bedroom guest-house - Medford - Living room
Chic & cozy 1 bedroom guest-house
Medford, OR
9.7Wonderful(15)
Apartment
$181+
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Your Southern Oregon Getaway - Medford - Living room
Your Southern Oregon Getaway
Medford, OR
9.7Wonderful(16)
House
$114+
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Enchanting 3 BR, minutes from Winerys, Snow Sking, exhilarating Rafting Tours. - Medford - Living room
Enchanting 3 BR, minutes from Winerys, Snow Sking, exhilarating Rafting Tours.
Medford, OR
10Wonderful(80)
House
$258+
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Game Room Fun! Medford Family Retreat - Medford
Game Room Fun! Medford Family Retreat
Medford, OR
9.9Wonderful(25)
House
$276+
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Pioneer Vacation Rentals - Pioneer Craftsman House - Ashland
Pioneer Vacation Rentals - Pioneer Craftsman House
Ashland, OR
8.5Very good(2)
House
$616+
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Classic & Cozy Apartments - Parking & Close To Dw - Medford
Classic & Cozy Apartments - Parking & Close To Dw
Medford, OR
8.8Very good(17)
Apartment
$150+
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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?

Tuesday offers the lowest rates in Ashland, with an average nightly price of $110. The highest prices are found on Sunday, with average rates at $322.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
June
$180
$184
Cheapest month to stay with an average 42% drop in price.
Most expensive month to stay with an average 142% 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 6% cheaper than hotels on average. Search here to compare prices for all accommodation types in Ashland.
  • The best vacation rental properties in Ashland are Enchanting 3 BR, minutes from Winerys, Snow Sking, exhilarating Rafting Tours. (10.0, 80 reviews), Brookdale Meadows sleeps 6 (10.0, 30), and Game Room Fun! Medford Family Retreat (9.9, 25), based on ratings and reviews from real travelers.
  • Downtown is the neighborhood in Ashland with the most affordable vacation rental properties (4 properties with an average price of $523 per night). 1907 Charmer, Perfect Downtown Location, So Clean!, High Street Cottage Artists' Garden Cottage Clean & Beautiful, and Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3 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 December.
  • The cheapest night for renting a vacation home in Ashland is Tuesday. In contrast, the most expensive is Sunday.
  • 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 $1,419.

  • 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 $6,082.

  • 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, 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 24% 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 $363. Search here for similar prices

  • How much is a vacation rental in Ashland for this weekend?

    In the last 72 hours, users have found Ashland vacation rentals for this weekend for as low as $267 per night. 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