Ashland Holiday Rentals
Check In Check Out
Any Bedrooms
Any Guests
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Max per night
£100
100
100
400
£200
200
200
800
£300
300
300
1200
£400
400
400
1600
£500
500
500
2000
£600
600
600
2400
£700
700
700
2800
£800
800
800
3200
£900
900
900
3600
£1,000+
+1000
+1000
+4000
Studio +
0,30
1 Bedroom +
1,30
2 Bedrooms +
2,30
3 Bedrooms +
3,30
4 Bedrooms +
4,30
5 Bedrooms +
5,30
6 Bedrooms +
6,30
7 Bedrooms +
7,30
8 Bedrooms +
8,30
Filters
clear all Bedrooms
Price
Neighbourhoods
Amenities
Filters
clear all Check In Check Out
There are no pins in your viewport. Try moving the map or changing your filters.
- {providername} {price}
{sold_out_text}
We can't find prices for this accommodation
From {rate_price} {rate_periodicity}
View Map
Location
Any Distance
from
Suitability
Bathrooms
Any
More filters
Amenities
More
Property type
More
Distinctive Features
All 99 Rentals in Ashland
Sort by:
Default
2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
Check in Check out
Payment Protection
7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
Check in Check out
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
Check in Check out
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Grill
- Cable/satellite TV
- Wi-Fi
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabin with...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Hot Tub
- Wi-Fi
- Parking
- Cable/satellite TV
- Grill
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabin with...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Air Conditioning
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
(NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Water Suite Cottage is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a kitchenette, living room with sofa-bed, flat panel 4K TV, one...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Balcony
- Washer
- Air Conditioning
- Private Garden
- Parking
- Wi-Fi
- Cable/satellite TV
- Terrace
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- DVD Player
- Parking
- Hot Tub
- Grill
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabin with...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Cable/satellite TV
- Private Garden
- Parking
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 8 July 2018
The location was terrific and close to downtown but very quiet and peaceful. The home was lovely, well done and plenty of space for our group. We loved the porch!!! All the...
About this property
Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from theaters, Plaza and Downtown.
Let this charming, historic home fill you with a sense of well-being and luxury. There are two bedrooms, each with a queen bed, and a...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Patio
- Parking
- Air Conditioning
- Mountain Views
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Parking
- Terrace
- Washer
- Wi-Fi
- Balcony
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Cable/satellite TV
- Parking
- Hot Tub
- Washer
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
The Anne Hathaway House was built in 1908 as a boarding house for travelers. David and Deedie Runkel purchased the home in 2002 and continue to operate it today. Located just four short blocks from the Oregon Shakespeare Festival, the Anne Hathaway House is ideal for large groups of theater goers,...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 13
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Air Conditioning
- Balcony
- Washer
- Parking
- Wi-Fi
- Terrace
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Washer
- Balcony
- Cable/satellite TV
- Wi-Fi
- Terrace
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Fully renovated - available May 1st, 2018
It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Wi-Fi
- Parking
- Washer
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
November 5th through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Balcony
- Cable/satellite TV
- Parking
- Air Conditioning
- Wi-Fi
- Washer
- Private Garden
- Terrace
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Hot Tub
- Washer
- Wi-Fi
- Cable/satellite TV
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Built in 2008, this home is adjacent to a historic home and one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine tasting, and shopping. Private,...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Wi-Fi
- Cable/satellite TV
- Washer
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Fully renovated - available May 2018
It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Wi-Fi
- Air Conditioning
- Washer
- Parking
- Balcony
- Private Garden
- Terrace
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Air Conditioning
- Cable/satellite TV
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Just five blocks from the Oregon Shakespeare Festival in a historic Ashland neighborhood...
Built in the early 1900's and fully renovated the Blue Moon House has it all! Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Parking
- Hot Tub
- Grill
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Welcome to your Hyatt Lake Cabin with Hot Tub! The master bedrooms both have a queen size bed, and the sleeping lofts both have two full beds. Full kitchen, dining room, and bathroom. The cabins both have bbqs, decks,...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Cable/satellite TV
- Air Conditioning
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
The Blue Moon Cottage is attached to the main home but has two private entrances. It offers a full kitchen, a gas fireplace, air conditioning, a separate bedroom with a comfy queen bed, a full bath with shower/tub combination and a private patio. There is also a flat screen television in the living...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Hot Tub
- Cable/satellite TV
- Grill
- Parking
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabin...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Cable/satellite TV
- Air Conditioning
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat panel...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Washer
- Air Conditioning
- Private Garden
- Balcony
- Cable/satellite TV
- Parking
- Wi-Fi
- Terrace
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Washer
- Cable/satellite TV
- Parking
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
November 5th through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
2 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Grill
- Wi-Fi
- Cable/satellite TV
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
(NOTE: Listed through the City of Ashland as Oak Street Cottages)
Built in the late 1800's, the Sherwin House is in the heart of Ashland and is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, a front yard with seating, two private...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 11
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Cable/satellite TV
- Balcony
- Washer
- Mountain Views
- Terrace
- Wi-Fi
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Sleeps 6 - Tesla Charging Station
Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Washer
- Cable/satellite TV
- Wi-Fi
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located just 20 miles from downtown Ashland, Whispering Pines Cabin is situated on private acreage adjacent to Hyatt Lake. This cabin is very private and sleeps up to 12 people, making it the perfect getaway for a large family or group. Swim, fish, or paddle on the lake in the summer or play in the...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Washer
- Private Garden
- Air Conditioning
- Parking
- Balcony
- Wi-Fi
- Cable/satellite TV
- Terrace
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Cable/satellite TV
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Located in the east Ashland countryside, and exactly three miles from the downtown Ashland Plaza and infamous Oregon Shakespeare Festival, this cottage has it all! The mountain views are stunning and the gardens alive with color in the spring and summer. Enjoy the whimsy and art found in the...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Grill
- Wi-Fi
- Parking
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
(NOTE: Listed through the City of Ashland as Oak Street Cottages)
Located in the heart of Downtown Ashland, Oak Lawn Cottage is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, living room with fireplace, flat panel TV, a patio, two...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Grill
- Hot Tub
- Cable/satellite TV
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your *PET FRIENDLY* Hyatt...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Wi-Fi
- Grill
- Hot Tub
- Cable/satellite TV
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your PREMIUM Hyatt Lake...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
Studio, 1 Bathroom, Sleeps 2 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Grill
- Cable/satellite TV
- Parking
- Wi-Fi
- Air Conditioning
- Washer
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
November 5th through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Light, bright and simply gorgeous, this charming studio is just a ten-minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon at any time of...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 1 Bathroom, Sleeps 2
2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Air Conditioning
- Grill
- Parking
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
(NOTE: Listed through the City of Ashland as Oak Street Cottages)
Located in the heart of Downtown Ashland, Oak Tower Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, and just one and half blocks to the Theaters. The home features a full kitchen, a patio, two...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Terrace
- Air Conditioning
- Patio
- Mountain Views
- Cable/satellite TV
- Wi-Fi
- Balcony
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Grill
- Wi-Fi
- Hot Tub
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabin with...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Wi-Fi
- Cable/satellite TV
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat panel...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Grill
- Parking
- Wi-Fi
- Hot Tub
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabin with a Hot...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Grill
- Cable/satellite TV
- Parking
- Hot Tub
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabins with a Hot Tub and lake views! The master bedrooms have queen beds. The sleeping loft in #51 has a queen and full bed. #52 has a...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- DVD Player
- Parking
- Cable/satellite TV
- Wi-Fi
- Grill
- Hot Tub
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Book your reservation for 2 nights and let us know you’d like the 3rd night free, we’ll enter that for you!!
Just eighteen miles east of downtown Ashland are The Cabins at...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Wi-Fi
- Air Conditioning
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
A working family farm just 5 minutes from downtown Ashland. Views of mountains can be enjoyed from YOUR private deck, with (seasonal) hops, grapes and blackberries growing right outside. This suite is bright and comfortable, with private entrance. It includes a Master Bedroom (queen bed), a...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Parking
- Grill
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Book your reservation for 2 nights and let us know you’d like the 3rd night free, we’ll enter that for you!!
Just eighteen miles east of downtown Ashland are The Cabins at...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Air Conditioning
- Wi-Fi
- Cable/satellite TV
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
November 5th through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
This home is brand new to the vacation rental market and is everything a family or small group is looking for. Close to restaurants and retailers... and less than five blocks...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Air Conditioning
- Cable/satellite TV
- Grill
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
(NOTE: Listed through the City of Ashland as Oak Street Cottages)
Located in the heart of Downtown Ashland, these cottages are one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, large living room with fireplace, flat panel TV, patio,...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Air Conditioning
- Wi-Fi
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
High above the hamlet of Ashland sits Bel Canto, a quiet home nestled in the hillside with stunning views of the charming town below. This immaculate space is situated on the lower level of the owner's home with private entry. Although you’ll feel a million miles away in this peaceful sanctuary,...
View all property information Location Information
Ashland, Oregon 97520
Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Parking
- Hot Tub
- Cable/satellite TV
- Grill
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Welcome to your Hyatt Lake Cabin with...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
3rd Night Free!!!
October 1st through April 30th
Black-Out Dates Apply on Holiday Weeks
Other restrictions may apply
Each Hyatt Lake cabin comes with wireless internet access, flat panel satellite TV, private deck, and lakefront or forest views. If you choose to dine out, The GreenSprings Inn...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Hot Tub
- Wi-Fi
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Just eighteen miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
Hyatt Lake Cabin Compound! Two cabins connected by a common deck. Two full kitchen, dining rooms, and two bathrooms. Two master bedrooms (queen beds) and two...
View all property information Location Information
Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
Ashland Holiday Rentals
Are you looking for the perfect holiday rental in Ashland, Ore.? Then come on in and take a look. Ashland, noted for its postcard picture perfect seasons, beautiful topography and friendly people, is the perfect holiday spot. Now that you’ve found it, you need someplace to stay. Rental cabins are a wonderful option and may be ideal for you and your family. Many are only a hop, skip and a jump from Ashland amenities, while affording you the privacy you desire. Make it a holiday to remember with a rental cottage, condo or cabin. With multiple price points and rental options, you’re sure to find something that fits your budget – and we can help.
Ashland Activities
If you’re looking for something to do while you’re in Ashland, head on over to the Oregon Shakespeare Festival. Each season brings something different for Shakespeare lovers ranging from tours to your favorite play. Other cultural events include the Oregon Cabaret Theater and the Ashland Independent Film Festival. Ashland is also home to more than 80 art galleries and multiple museums, such as the ScienceWorks Hands On Museum for children and the Ashland Art Center. From your home away from home holiday rental, plan your day around the activities that suit you best!
Romancing Ashland
Of course, with its beautiful location at the base of the Cascade Mountain Range, Ashland is perfect for lovers. Let us help you find a quaint rental cottage for two, while you focus on romance! Wine and dine with the best of them at several area restaurants including Chateaulin French restaurant. Here, you’ll find the perfect ambiance in the intimate and romantic dining room as well as an extensive wine list and gourmet French food. Or try the nationally acclaimed Winchester Restaurant at the Winchester Inn. Take your chocolate loving sweetie to the Oregon Chocolate Festival or go for a bike ride on the Mt. Ashland Mountain Bike Trail.
Ashland is for Skiing and Golf
With several mountain ranges in the Southern Oregon area, Ashland is perfect for the ski enthusiast! Hit the slopes at any one of the area resorts with trails ranging from beginner to professional, cross country to downhill. Find a rental cabin with access just outside your door and you’ll be in ski heaven. Located at 7,500 feet, Mt. Ashland offers skiing during the season from November to April on a variety of trails for any skill level as well as snowboarding. Golf resorts include Oak Knoll in Ashland and Centennial Golf Club in nearby Medford.
© 2018 TripAdvisor LLC All rights reserved.
* TripAdvisor LLC is not a booking agent and does not charge any service fees to users of our site... (more)
TripAdvisor LLC is not responsible for content on external web sites. Taxes, fees not included for deals content.