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Ashland Pet Friendly Rentals

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    Travelers to Ashland are booking November dates now. Secure your vacation rental today, and have the perfect trip.
    25 Matching Rentals in AshlandView all 98 rentals
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    ArtYcottage  UNBELIEVEABLE...1 / 16
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Singing Birds Cabin1 / 15
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stay Ashland like never before.  Explore days, campfire stars at night!1 / 13
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Pelton Villa1 / 12
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Patio
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2018
    Our family of 4 stayed 2 nights in the Earth Suite because everything else was booked. We would've stayed 3 if it had been available. We walked to OSF, downtown for meals, and...
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    About this property
    Experience Ashland like a local. Pelton Vacation Rental in downtown Ashland is the place to be. We have 3 private units: The Villa main house, Earth suite carriage house, and Water suite carriage house. As a vacation rental, other than having the best location in Ashland, we offer our guests...
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    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Private Yard
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Washer
    • Patio
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is located on our ranch. It is 5 miles from downtown Ashland. It is 3 miles to local airport & 3.5 miles to local golf course. The views of the mountains, pastures, wildlife, cows & horses are very beautiful. It is relaxing and enjoyable. This home has hardwood floors. It is a...
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    Ashland, Oregon 97520
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
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    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
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 13
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    2 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
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    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...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 11
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    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...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    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 is close by and offers dining and entertainment throughout much of the year. Looking for watercraft rentals? Let us know...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Private Yard
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Yard
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
    View all property information
    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Private Yard
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience Ashland like a local. Pelton Vacation Rental in downtown Ashland is the place to be. As a vacation rental, other than having the best location in Ashland, we offer our guests many in-room complimentary amenities. With the intention of making Pelton environmentally friendly, we use...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    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!!! Welcome to your *PET FRIENDLY* Hyatt Lake Cabin with Hot Tub! The master bedroom has a queen size bed, and the sleeping loft has two full beds. Full kitchen,...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Carlisle Garden Suites - Viola Suite1 / 14
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 2, 2018
    We just spent one night here, but wish we could have stayed longer. It was a lovely spot, 4 blocks from down town Ashland. We stayed in the Camomile Suite, which had a king bed...
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    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
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    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,...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
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    Location Information
    Ashland, Oregon 97520
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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