Vacation Rentals in Ashland, OR
PRICE PER NIGHT
ACCOMMODATION TYPES
Light, Bright Gorgeous New Cottage! 15-min Walk to Plaza, OSF. Sparkling Clean!
9.7
Excellent
·
Ashland
·
1 br
·
Sleeps 3
·
Outdoor Space · Workspace · Fitness Center ·
From
$190/nightProperty
House · 1 Bed · 1 bath
Amenities
Fitness Center
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Residents Lounge
Other spaces
Workspace, Kitchen
BookStayHop - Blue Moon House ~ Just Five Blocks from OSF!~ Gourmet Kitchen
9
Excellent
·
Ashland
·
5 br
·
Sleeps 11
·
Deck · Assigned Parking · Fireplace ·
From
$744/nightProperty
House · 5 Beds · 5 baths
Amenities
Assigned Parking
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Deck, Balcony, Kitchen
BookStayHop - The Pioneer House - South Suite (Downstairs) - Closest to OSF!
9.6
Excellent
·
Ashland
·
3 br
·
Sleeps 8
·
Dishwasher · Balcony · Kitchen ·
From
$156/nightProperty
House · 3 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
BookStayHop - Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF ~ Kitchen
8.9
Very good
·
Ashland
·
1 br
·
Sleeps 4
·
Fireplace · Dishwasher · Balcony ·
From
$243/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
BookStayHop - The Pioneer House -North Suite (Upstairs) - Closest to OSF!
9.7
Excellent
·
Ashland
·
2 br
·
Sleeps 6
·
Dishwasher · Balcony · Kitchen ·
From
$220/nightProperty
House · 2 Beds · 1 bath
Amenities
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
BookStayHop - Anne Hathaway's House ~ Just 4 blocks from OSF!~ Kitchen
9.2
Excellent
·
Ashland
·
7 br
·
Sleeps 14
·
Dishwasher · Balcony · Oven ·
From
$991/nightProperty
House · 7 Beds · 9 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
BookStayHop - Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ 5 Blocks to Downtown Ash
9.1
Excellent
·
Ashland
·
2 br
·
Sleeps 4
·
Wifi · Balcony · Oven ·
From
$267/nightProperty
House · 2 Beds · 1 bath
Amenities
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Studio with King-Size Bed
No reviews
·
Ashland
·
1 br
·
Sleeps 2
·
On Site Laundry · Free Parking · Assigned Parking ·
From
$180/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Free Parking
Assigned Parking
Wifi
Furnished
The best of Zumper, delivered
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Stone's Throw Bungalow ~ Walk to Plays, Licensed/Legal, Private Entrance, Garden
10
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Ceiling Fan · Outdoor Space · Mountains ·
From
$160/nightProperty
House · 1 Bed · 1 bath
Amenities
Ceiling Fan
Mountains
Fitness Center
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
BookStayHop - Lori Lane Compound ~ 5 blocks from Downtown Ashland ~Kitchen ~Main
10
Excellent
·
Ashland
·
7 br
·
Sleeps 14
·
Fireplace · Wifi · Dishwasher ·
From
$935/nightProperty
House · 7 Beds · 5 baths
Amenities
Fireplace
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Adorable downtown cottage, one block from OSF and Lithia Park
9.9
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Ski In Ski Out · Mountains · Wifi ·
From
$179/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Ski In Ski Out
Mountains
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
BookStayHop - The Pioneer ~ Closest to OSF!
No reviews
·
Ashland
·
8 br
·
Sleeps 22
·
Fireplace · Dishwasher · Balcony ·
From
$806/nightProperty
House · 8 Beds · 5 baths
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
230-Downstairs-Duplex-Private Bathroom-Mountain View
9.7
Excellent
·
Ashland
·
3 br
·
Sleeps 6
·
Hardwood Floor · Wifi · Dishwasher ·
From
$308/nightProperty
House · 3 Beds · 2 baths
Amenities
Hardwood Floor
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
232-Duplex-Private Bathroom-Mountain View
10
Excellent
·
Ashland
·
3 br
·
Sleeps 6
·
Hardwood Floor · Ski In Ski Out · Wifi ·
From
$314/nightProperty
House · 3 Beds · 2 baths
Amenities
Hardwood Floor
Ski In Ski Out
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
BookStayHop - Blue Moon House & Cottage ~ Just 5 Blocks from OSF~ Gourmet Kitche
10
Excellent
·
Ashland
·
6 br
·
Sleeps 15
·
Deck · Assigned Parking · Fireplace ·
From
$838/nightProperty
House · 6 Beds · 6 baths
Amenities
Assigned Parking
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Deck, Balcony, Kitchen
Expansive views at The Crest House
10
Excellent
·
Ashland
·
3 br
·
Sleeps 6
·
Assigned Parking · Wifi · Dishwasher ·
From
$373/nightProperty
House · 3 Beds · 1 bath
Amenities
Assigned Parking
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
BookStayHop - The Pioneer North & South - Closest to OSF!
10
Excellent
·
Ashland
·
5 br
·
Sleeps 14
·
Dishwasher · Balcony · Kitchen ·
From
$313/nightProperty
House · 5 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
9.8
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Ski In Ski Out · Outdoor Space · Workspace ·
From
$148/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Ski In Ski Out
Mountains
Fitness Center
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Balcony, Kitchen
BookStayHop - The Pioneer - Craftsman House - Closest to OSF!
9.6
Excellent
·
Ashland
·
3 br
·
Sleeps 8
·
Fireplace · Dishwasher · Balcony ·
From
$156/nightProperty
House · 3 Beds · 2 baths
Amenities
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Stacy's 2nd St Cottage. Steps to downtown.
10
Excellent
·
Ashland
·
2 br
·
Sleeps 4
·
Ev Charging · Outdoor Space · Hot Tub ·
From
$275/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Ev Charging
Hot Tub
Fitness Center
Fireplace
Wifi
Dishwasher
Oven
In Unit Laundry
Other spaces
Kitchen
Ashland's new vacation rental.
9.8
Excellent
·
Ashland
·
2 br
·
Sleeps 6
·
Lake · Waterfront · Mountains ·
From
$195/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Lake
Waterfront
Mountains
Fitness Center
Wifi
Dishwasher
Oven
In Unit Laundry
Other spaces
Kitchen
Romantic and Unique “Industrial Tuscan” home walking distance to town
No reviews
·
Ashland
·
2 br
·
Sleeps 4
·
Outdoor Space · Workspace · Mountains ·
From
$165/nightProperty
House · 2 Beds · 3 baths
Amenities
Mountains
Fitness Center
Fireplace
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Other spaces
Workspace, Balcony, Kitchen
High Street Cottage Artists' Garden Cottage Clean & Beautiful
10
Excellent
·
Ashland
·
2 br
·
Sleeps 4
·
Fireplace · Wifi · Dishwasher ·
From
$195/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Fireplace
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
The Terra Cottage Inn - Ashland, Oregon
9.9
Excellent
·
Ashland
·
2 br
·
Sleeps 4
·
Coffee Tea Maker · Hardwood Floor · Mountains ·
From
$185/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Coffee Tea Maker
Hardwood Floor
Mountains
Fitness Center
Wifi
Dishwasher
Oven
In Unit Laundry
Other spaces
Kitchen
Bayberry Inn B&B
9.4
Excellent
·
Ashland
·
1 br
·
Sleeps 3
·
Carpet · On Site Laundry · Smoking Allowed ·
From
$236/nightProperty
Hotel · 1 Bed
Amenities
Carpet
On Site Laundry
Smoking Allowed
Free Parking
Assigned Parking
Fireplace
Wifi
Air Conditioning
Other spaces
Workspace, Balcony, Kitchen
BookStayHop - Peerless Entire Hotel ~ Downtown Ashland
No reviews
·
Ashland
·
6 br
·
Sleeps 12
·
Dishwasher · Balcony · Oven ·
From
$1,127/nightProperty
House · 6 Beds · 6 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Storage
Other spaces
Balcony, Kitchen
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
9.8
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Smoking Allowed · Lake · Waterfront ·
From
$99/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Smoking Allowed
Lake
Waterfront
Ski In Ski Out
Mountains
Wifi
Dishwasher
Oven
Other spaces
Workspace, Kitchen
BookStayHop - Peerless Hotel~ Suite 3 ~ Downtown Ashland
10
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Fireplace · Balcony · In Unit Laundry ·
From
$197/nightProperty
House · 1 Bed · 1 bath
Amenities
Fireplace
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony
BookStayHop - Peerless Hotel~ Guest Room 2 ~Downtown Ashland
10
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Hot Tub · Balcony · In Unit Laundry ·
From
$185/nightProperty
House · 1 Bed · 1 bath
Amenities
Hot Tub
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony
BookStayHop - Peerless Hotel ~ Guest Room 1 ~ Downtown Ashland
No reviews
·
Ashland
·
1 br
·
Sleeps 2
·
Balcony · In Unit Laundry · Air Conditioning ·
From
$185/nightProperty
House · 1 Bed · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Storage
Other spaces
Balcony
BookStayHop - Peerless Hotel~ Suite 7 ~Downtown Ashland
No reviews
·
Ashland
·
1 br
·
Sleeps 2
·
Hot Tub · Fireplace · Balcony ·
From
$237/nightProperty
House · 1 Bed · 1 bath
Amenities
Hot Tub
Fireplace
In Unit Laundry
Air Conditioning
Furnished
Elevator
Other spaces
Balcony
BookStayHop - Peerless Hotel~ Guest Room 5 ~Downtown Ashland
10
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Hot Tub · Balcony · In Unit Laundry ·
From
$187/nightProperty
House · 1 Bed · 1 bath
Amenities
Hot Tub
In Unit Laundry
Air Conditioning
Furnished
Elevator
Storage
Other spaces
Balcony
BookStayHop - Peerless Hotel~ Guest Room 6~ Downtown Ashland
10
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Balcony · In Unit Laundry · Air Conditioning ·
From
$185/nightProperty
House · 1 Bed · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Elevator
Other spaces
Balcony
Courtside Cottage - WalkScore 93 - Dog Friendly
10
Excellent
·
Ashland
·
1 br
·
Sleeps 4
·
Wifi · In Unit Laundry · Furnished ·
From
$117/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Wifi
In Unit Laundry
Furnished
BookStayHop - Peerless Suites 1, 2 and 5
No reviews
·
Ashland
·
3 br
·
Sleeps 6
·
Hot Tub · Balcony · In Unit Laundry ·
From
$548/nightProperty
House · 3 Beds · 3 baths
Amenities
Hot Tub
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony
BookStayHop - Peerless Suites 1 and 2
No reviews
·
Ashland
·
2 br
·
Sleeps 4
·
Hot Tub · Balcony · In Unit Laundry ·
From
$365/nightProperty
House · 2 Beds · 2 baths
Amenities
Hot Tub
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony
BookStayHop - Plaza North (201-203) Suites Trinity
No reviews
·
Ashland
·
4 br
·
Sleeps 12
·
High Ceilings · Mountains · Fireplace ·
From
$1,042/nightProperty
Condo · 4 Beds · 6 baths
Amenities
High Ceilings
Mountains
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Downtown Ashland private cottage with garden patio
9.8
Excellent
·
Ashland
·
1 br
·
Sleeps 3
·
Ev Charging · Fitness Center · Wifi ·
From
$160/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Ev Charging
Fitness Center
Wifi
In Unit Laundry
Air Conditioning
Furnished
Elevator
Other spaces
Kitchen
BookStayHop - RedTail ~Louisa Suite~Tesla Station~ 4 Blocks to OSF!
10
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Workspace · Hot Tub · Dishwasher ·
From
$187/nightProperty
House · 1 Bed · 1 bath
Amenities
Hot Tub
Dishwasher
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Workspace, Balcony, Kitchen
BookStayHop - RedTail ~ McCall Suite~Tesla Station~ 4 Blocks to OSF!
10
Excellent
·
Ashland
·
2 br
·
Sleeps 6
·
Hot Tub · Mountains · Dishwasher ·
From
$276/nightProperty
House · 2 Beds · 1 bath
Amenities
Hot Tub
Mountains
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Residents Lounge
Other spaces
Balcony, Kitchen
BookStayHop - The Barclay-Klum House ~ South (Downstairs) Suite~3 Minutes to Pla
9.6
Excellent
·
Ashland
·
2 br
·
Sleeps 4
·
High Ceilings · Dishwasher · Balcony ·
From
$196/nightProperty
House · 2 Beds · 1 bath
Amenities
High Ceilings
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
BookStayHop - RedTail Suites ~ Entire Home ~ Sleeps 12 ~ Tesla Station~ 4 Blocks
10
Excellent
·
Ashland
·
4 br
·
Sleeps 12
·
Workspace · Hot Tub · Mountains ·
From
$569/nightProperty
House · 4 Beds · 3 baths
Amenities
Hot Tub
Mountains
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Residents Lounge
Other spaces
Workspace, Balcony, Kitchen
BookStayHop - RedTail Suites~Orliena Suite~Tesla Station ~ 4 Blocks to OSF!
10
Excellent
·
Ashland
·
1 br
·
Sleeps 4
·
Hot Tub · Dishwasher · Balcony ·
From
$234/nightProperty
House · 1 Bed · 1 bath
Amenities
Hot Tub
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Residents Lounge
Other spaces
Balcony, Kitchen
Studio with King-Sized Bed
No reviews
·
Ashland
·
1 br
·
Sleeps 2
·
Wifi · Oven · Furnished ·
From
$132/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Wifi
Oven
Furnished
Top floor of modern duplex - walk to plays, SOU, Lithia Park
10
Excellent
·
Ashland
·
1 br
·
Outdoor Space · Mountains · Fitness Center ·
From
$50/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Mountains
Fitness Center
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
COZY cottage near Lithia Park and Town! Ashland, OR
10
Excellent
·
Ashland
·
1 br
·
Sleeps 2
·
Fitness Center · Wifi · Balcony ·
From
$56/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Wifi
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Home Sweet Home - Relax w/ Beautiful Big Yard and Steam Shower
8
Very good
·
Ashland
·
3 br
·
Sleeps 8
·
Pool · Ski In Ski Out · Fitness Center ·
From
$280/nightProperty
House · 3 Beds · 2 baths
Amenities
Pool
Ski In Ski Out
Fitness Center
Fireplace
Wifi
Dishwasher
Oven
In Unit Laundry
Other spaces
Kitchen
The Ashland Cottage, walk to town
9.9
Excellent
·
Ashland
·
1 br
·
Sleeps 4
·
High Ceilings · Fireplace · Wifi ·
From
$170/nightProperty
Apartment · 1 Bed · 2 baths
Amenities
High Ceilings
Fireplace
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
9.7
Excellent
·
Ashland
·
2 br
·
Sleeps 6
·
Ski In Ski Out · Fitness Center · Wifi ·
From
$187/nightProperty
House · 2 Beds · 2 baths
Amenities
Ski In Ski Out
Fitness Center
Wifi
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Kitchen
The Maple Apartment at Tudor House Vacation Rentals
9.4
Excellent
·
Ashland
·
2 br
·
Sleeps 6
·
Fitness Center · Wifi · Kitchen ·
From
$169/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Fitness Center
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Showing 1 - 50 of 109 results
Updated: March 25, 2023
Learn about vacation rentals in
Ashland
Explore 110 vacation rentals near Ashland, Oregon. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Ashland, you can see photos of Ashland vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Ashland vacation rentals in specific areas. Whether you’re looking for a Ashland staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Ashland is $50 per night and the highest price is $1,127 per night.
21 of the vacation rentals near Ashland are
apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation
units is $174 per night. There are
currently 14 vacation units under this
price. 64 of the vacation rentals near Ashland are houses.
The average bathroom count for a vacation house near Ashland is
2. The average price for vacation houses near Ashland is $378 per night. There are 49 vacation homes under this price. The most common
amenities for vacation rentals near Ashland are: furnished, air conditioning, and in-unit laundry. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
47 available
2 bed rentals
27 available
3 bed rentals
18 available
4+ bed rentals
15 available
Getting around Ashland
Walking
4/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Points of interest in Ashland
Groceries
5/10
At least one grocery store within a 30-minute walk
Shopping
2/10
Few or no shops within walking distance
Cafes
3/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Nightlife
2/10
Few or no bars within walking distance
Vacation Rentals in Ashland, OR FAQ
How many vacation rentals in Ashland are available?
There are currently 110 vacation rentals in Ashland available. Our vacation rentals in Ashland include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Ashland?
Yes, right now there are 24 pet friendly vacation rentals in Ashland. A pet friendly vacation rental in Ashland means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Ashland with a pool?
Yes there are vacation rentals with a pool available in Ashland, OR. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Ashland with internet access?
As of March 25, 2023, there are vacation rentals with internet access available in Ashland, Oregon. Check out more enjoyable destinations on Vacations by Zumper.
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