Vacation Rentals in Ashland, OR

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Ashland, OR

Book a vacation rental in Ashland that has the highest visitor rating. Here are 6 of the best vacation rentals in Ashland.
Price drop
Family Getaway: Enjoy a Pool, Hot Tub, and Peloton
10

Excellent

·
Ashland
·
3 br
·
Sleeps 10
·
Hot Tub · Kitchen · Balcony ·
From
$354/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Hot Tub
Private Pool
Residents Lounge
Garage Parking
Furnished
In Unit Laundry
Mountains
Fitness Center
Other spaces
Kitchen, Balcony, Workspace
Price drop
Luxury Stay - 4BR w/ Pool, HotTub, Peloton & Sauna
10

Excellent

·
Ashland
·
4 br
·
Sleeps 12
·
Fitness Center · Kitchen · Outdoor Space ·
From
$400/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Fitness Center
Wifi
In Unit Laundry
Residents Lounge
Swimming Pool
Dishwasher
Pool
Garage Parking
Other spaces
Kitchen, Workspace, Balcony
Price drop
Titania - Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
10

Excellent

·
Ashland
·
1 br
·
Sleeps 3
·
Fitness Center · Wifi · Walk In Closets ·
From
$209/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Wifi
Walk In Closets
Dishwasher
Air Conditioning
Oven
In Unit Laundry
Furnished
Other spaces
Kitchen, Balcony
In the historic railroad district, walking distance to all the best of Ashland!
10

Excellent

·
Ashland
·
4 br
·
Sleeps 8
·
Oven · Kitchen · Furnished ·
From
$450/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Oven
Furnished
Dishwasher
Wifi
Fitness Center
Hardwood Floor
In Unit Laundry
Air Conditioning
Other spaces
Kitchen
Price drop
In the Heart of Town, Charming Historic Home, Quintessential Ashland!
10

Excellent

·
Ashland
·
3 br
·
Sleeps 8
·
Oven · Wifi · In Unit Laundry ·
From
$375/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Oven
Wifi
In Unit Laundry
Fitness Center
Ski In Ski Out
Furnished
Air Conditioning
Mountains
Other spaces
Kitchen
Price drop
Courtside Cottage - WalkScore 93 - Dog Friendly
10

Excellent

·
Ashland
·
1 br
·
Sleeps 4
·
Wifi · Outdoor Space · Kitchen ·
From
$168/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Kitchen

Our Recommended Vacation Rentals in Ashland, OR

We analyzed vacation rentals in Ashland from many property providers including but not limited to VRBO, Booking.com, Evolve, Blueground and more. We're providing our top recommended offers on the best vacation rentals in Ashland to help you find a deal for your next trip.
Price drop
Redtail Inn - 3 Suites Sleeps 12

No rating

·
Ashland
·
4 br
·
Sleeps 12
·
Smoking Allowed · Wifi · Free Parking ·
From
$336/night
Check availability
Property
Hotel · 4 Beds · 2 baths
Amenities
Smoking Allowed
Wifi
Free Parking
Air Conditioning
Dishwasher
Oven
Furnished
Hot Tub
Other spaces
Kitchen, Workspace
Warm and Inviting Ashland Cottage Less Than Half-Mile to SOU

No rating

·
Ashland
·
1 br
·
Sleeps 2
·
Wifi · Kitchen · Outdoor Space ·
From
$269/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Fireplace
Furnished
Oven
In Unit Laundry
Free Parking
Air Conditioning
Other spaces
Kitchen
Second Street Cottages
9.6

Excellent

·
Ashland
·
1 br
·
Sleeps 4
·
Outdoor Space · Air Conditioning · Free Parking ·
From
$117/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Air Conditioning
Free Parking
Ski In Ski Out
Assigned Parking
Furnished
Carpet
On Site Laundry
Wifi
Price drop
The Matriarch Heritage House- Downtown Ashland

No rating

·
Ashland
·
2 br
·
Sleeps 4
·
Dishwasher · Wifi · Furnished ·
From
$323/night
Check availability
Property
House · 2 Beds · 3 baths
Amenities
Dishwasher
Wifi
Furnished
Air Conditioning
In Unit Laundry
Other spaces
Balcony, Kitchen

Budget-Friendly Vacation Rentals in Ashland, OR

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Ashland starting at $40. Use the price filter at the top of the page to search for more specific prices.
Charming, Comfortable Garden Studio Above The University.
10

Excellent

·
Ashland
·
Studio
·
Sleeps 3
·
Storage · Workspace · Kitchen ·
From
$40/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Storage
Air Conditioning
Furnished
Oven
Wifi
Fitness Center
In Unit Laundry
Other spaces
Workspace, Kitchen
One Block To Theater, Park And Town -- Walk Everywhere!
10

Excellent

·
Ashland
·
1 br
·
Sleeps 4
·
Furnished · In Unit Laundry · Fitness Center ·
From
$48/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
In Unit Laundry
Fitness Center
Dishwasher
Hot Tub
Air Conditioning
Garage Parking
Other spaces
Kitchen
Top floor of modern duplex - walk to plays, SOU, Lithia Park
10

Excellent

·
Ashland
·
1 br
·
Sleeps 2
·
Oven · Dishwasher · Air Conditioning ·
From
$50/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Oven
Dishwasher
Air Conditioning
Wifi
Mountains
Fitness Center
Furnished
In Unit Laundry
Other spaces
Kitchen, Balcony
October! COZY cottage near Lithia Park and Town! Ashland, OR
10

Excellent

·
Ashland
·
1 br
·
Sleeps 2
·
Hot Tub · Fitness Center · Outdoor Space ·
From
$56/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Hot Tub
Fitness Center
Oven
Wifi
In Unit Laundry
Furnished
Air Conditioning
Other spaces
Balcony, Kitchen
Available October 12-January 30th. Spacious Historic House one block to Town!

No rating

·
Ashland
·
1 br
·
Sleeps 2
·
Balcony · On Site Laundry · Workspace ·
From
$60/night
Check availability
Property
House · 1 Bed · 1 bath
Amenities
On Site Laundry
Ski In Ski Out
In Unit Laundry
Furnished
Hardwood Floor
Wifi
Air Conditioning
Fitness Center
Other spaces
Balcony, Workspace, Kitchen
Adjacent to Downtown Ashland and Lithia Park, Lithia Park Suite 3

No rating

·
Ashland
·
1 br
·
Sleeps 2
·
Wifi · Air Conditioning · Workspace ·
From
$70/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
In Unit Laundry
Furnished
Oven
Mountains
Other spaces
Workspace, Kitchen
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Updated: October 3, 2023