Vacation Rentals in Ashland, OR

136 rentals

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.
Swank House on Main St in Ashland
10

Excellent

·
Ashland
·
2 br
·
Sleeps 4
·
Free Parking · Kitchen · Furnished ·
From
$380/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Free Parking
Furnished
Wifi
Air Conditioning
Other spaces
Kitchen
Railroad District, steps to downtown, everything you need to enjoy Ashland!
10

Excellent

·
Ashland
·
2 br
·
Sleeps 5
·
Lake · Oven · Mountains ·
From
$365/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Lake
Oven
Mountains
Hardwood Floor
Dishwasher
Fitness Center
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Luxury Family Retreat-fully loaded house with pool
10

Excellent

·
Ashland
·
4 br
·
Sleeps 12
·
Workspace · Pool · Kitchen ·
From
$590/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Pool
In Unit Laundry
On Site Laundry
Wifi
Dishwasher
Residents Lounge
Oven
Swimming Pool
Other spaces
Workspace, Kitchen, Balcony
Courtside Cottage - WalkScore 93 - Dog Friendly
10

Excellent

·
Ashland
·
1 br
·
Sleeps 4
·
Wifi · Outdoor Space · Kitchen ·
From
$186/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Air Conditioning
In Unit Laundry
Furnished
Other spaces
Outdoor Space, Kitchen
Walkable Escape Perfect for Groups
10

Excellent

·
Ashland
·
4 br
·
Sleeps 16
·
Assigned Parking · Outdoor Space · On Site Laundry ·
From
$207/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Assigned Parking
On Site Laundry
Air Conditioning
In Unit Laundry
Furnished
Oven
Central Heat
Wifi
Other spaces
Outdoor Space, Kitchen
Expansive views at The Crest House
10

Excellent

·
Ashland
·
3 br
·
Sleeps 5
·
Oven · Dishwasher · Air Conditioning ·
From
$346/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Oven
Dishwasher
Air Conditioning
Assigned Parking
In Unit Laundry
Furnished
Wifi
Other spaces
Balcony, 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.
The Matriarch Heritage House- Downtown Ashland

No rating

·
Ashland
·
2 br
·
Sleeps 4
·
Air Conditioning · Outdoor Space · Free Parking ·
From
$429/night
Check availability
Property
Apartment · 2 Beds · 3 baths
Amenities
Air Conditioning
Free Parking
Dishwasher
Furnished
Wifi
Other spaces
Outdoor Space, Kitchen
The Matriarch- Downtown Ashland, OR
9.5

Excellent

·
Ashland
·
1 br
·
Sleeps 2
·
Free Parking · Air Conditioning · Wifi ·
From
$165/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Free Parking
Air Conditioning
Wifi
Assigned Parking
Furnished
Other spaces
Kitchen
Redtail Inn - 3 Suites Sleeps Up To 12

No rating

·
Ashland
·
4 br
·
Sleeps 12
·
Balcony · In Unit Laundry · Free Parking ·
From
$662/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
In Unit Laundry
Free Parking
Air Conditioning
Dishwasher
Smoking Allowed
Hot Tub
Furnished
Wifi
Other spaces
Balcony, Kitchen
Modern Luxe Crash Pad- Pet Friendly

No rating

·
Ashland
·
1 br
·
Sleeps 2
·
Free Parking · Kitchen · Air Conditioning ·
From
$140/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Free Parking
Air Conditioning
Wifi
Furnished
Other spaces
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 $42. 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
$42/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Storage
Air Conditioning
Furnished
Oven
Wifi
Fitness Center
In Unit Laundry
Other spaces
Workspace, Kitchen, Outdoor Space
395 E Main St #3

No rating

·
Ashland
·
1 br
·
Onsite Management · Central Heat · In Unit Laundry ·
From
$43/night
Min stay: 30 nights
Property
Condo · 1 Bed · 1 bath
Amenities
Onsite Management
Central Heat
In Unit Laundry
Dishwasher
395 E Main St #6

No rating

·
Ashland
·
1 br
·
Hardwood Floor · Central Heat · Dishwasher ·
From
$45/night
Min stay: 30 nights
Property
Condo · 1 Bed · 1 bath
Amenities
Hardwood Floor
Central Heat
Dishwasher
In Unit Laundry
Onsite Management
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
COZY cottage near Park and Town!!
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
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Updated: February 24, 2024