Ashland Holiday Rentals
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All 100 Rentals in Ashland
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2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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- Parking
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- Balcony
- Cable/satellite TV
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- Terrace
- Air Conditioning
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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
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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- 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
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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...
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Ashland, Oregon 97520
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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...
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Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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- Air Conditioning
- Wi-Fi
- Parking
- Washer
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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...
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Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
7 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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- 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,...
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Ashland, Oregon 97520
Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 12
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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...
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Ashland, Oregon 97520
Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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- Parking
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- Cable/satellite TV
- Washer
- Air Conditioning
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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 4 Quick View
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Amenities & Details
- Washer
- Porch
- Cable/satellite TV
- Patio
- DVD Player
- Internet Access
- Air Conditioning
- Grill
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 24 March 2018
The columnist Herb Caen wrote of the San Franciscan native who died and went to Heaven. Saint Peter met him at the Pearly Gates and gave him a tour of his new eternal home. When...
Reviewed 4 March 2016
My boyfriend and I did "experience" gifts for each other at Christmas and this was mine to him. We loved it! Fantastic craftsman cottage with all the amenities you need...
About this property
Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully equipped kitchen. A truly...
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Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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- 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,...
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Ashland, Oregon 97520
Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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Amenities & Details
- Cable/satellite TV
- Wi-Fi
- Mountain Views
- Secure Parking
- Outdoor Dining Area
- Air Conditioning
- Shared Garden
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 24 September 2015
Beautiful spot, wonderful cottage, perfect for the four of us. Less than a 5 minute drive to down town Ashland with it's fabulous plays, restaurants and shopping. Lovely new...
Reviewed 6 May 2015
Abigail's has new owners, who we found to be friendly and helpful. Super clean cottage, walked to plays two times a day. Great time
About this property
Abigail's Cottage within walking distance to the city center, is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes.
Comfortable two bedroom 1 1/2 bath cottage, completely renovated...
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Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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
3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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
4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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Amenities & Details
- Cable/satellite TV
- Balcony
- Private Garden
- Air Conditioning
- DVD Player
- Terrace
- Parking
- Wi-Fi
Suitability
Pet friendly
Kid friendly
Smoking allowed
Reviewed 31 October 2018
I have stayed at 2nd Street Cottages before and it continues to be our favorite vacation rental in Ashland. Such a well kept and beautiful Cottage. The owner pays such great...
Reviewed 15 April 2017
I would go back to Ashland just to stay here. Seriously. We were passing through on our way to California and needed somewhere tho spend the night. What a lucky accident! The...
About this property
THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY.
Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail...
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Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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...
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Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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
1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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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...
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Ashland, Oregon 97520
Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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Amenities & Details
- Air Conditioning
- Wi-Fi
- Patio
- Parking
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...
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Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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
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 6 Quick View
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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
- 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...
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Ashland, Oregon 97520
Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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
4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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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 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
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
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
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, 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 4 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Wi-Fi
- Air Conditioning
- 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, 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 4 Quick View
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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...
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Ashland, Oregon 97520
Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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
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, 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
- 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 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
Reviewed 2 weeks ago
The boyfriend and I wanted to get away from life for a long weekend for my birthday. The cabin was exactly as described, with a cute little sleeping loft, with a video game...
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 6 Quick View
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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
4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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- 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...
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Ashland, Oregon 97520
Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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- Washer
- Cable/satellite TV
- Wi-Fi
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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...
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Ashland, Oregon 97520
Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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- Wi-Fi
- Air Conditioning
- Parking
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Pet friendly
Kid friendly
Smoking allowed
About this property
Park-like setting, high above Ashland, yet very close to town
Tucked away in a canyon filled with Aspen and Pine trees, this quiet retreat is conveniently located just a five-minute drive from downtown Ashland. Guests have access to the grounds which are located in a well-maintained, park-like...
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Ashland, Oregon 97520
Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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
2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
Check in Check out
Payment Protection
Amenities & Details
- Cable/satellite TV
- Washer
- Internet Access
- Parking
Suitability
Pet friendly
Kid friendly
Smoking allowed
About this property
Just twenty miles east of downtown Ashland are The Cabins at Hyatt Lake
Over 200 Recent Reviews - Averaging 4.85 out of 5.0 STARS!!!
ALL NEW!
Welcome to your Hyatt Lake Cabin with lake views! Two bedrooms, each with a queen size bed. There is also a queen air mattress. Full kitchen, dining...
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
- Grill
- Hot Tub
- 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
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
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
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
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
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.
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