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Pet Friendly Holiday Rentals in Ashland

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    Travellers to Ashland are booking November dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in AshlandView all 95 rentals
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    ArtYcottage  UNBELIEVEABLE...1 / 16
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF1 / 10
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is not just pet-friendly, but pet-welcoming. This beautifully restored Farm House is divided into a two suite home a short walk from the Oregon Shakespeare Festival and the joys of downtown Ashland. With a king sized bed in the bedroom and a twin and queen upstairs. (and a bed for your...
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    97520, Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just blocks away from the Oregon Shakespeare Festival theaters downtown, Courtside Cottage is the perfect place to land on your next visit to Ashland. Park your car and live like a local in the heart of town. This convenient location is around the corner from the Growler Guys taphouse....
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    97520, Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Wi-Fi
    • Grill
    • Washer
    • Private Garden
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on 5 rural acres just outside of Ashland, Earth Cottage the perfect landing place for a contemplative retreat from the busy-ness of city life. Mature trees and native landscaping provide lots of shade and natural beauty. There’s even a treehouse just right for smaller travelers and a...
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    97520, Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Private Garden
    • Cable/satellite TV
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Suite with private garden access just one block from downtown. Located at the rear of a historic Craftsman bungalow, this private suite has a separate entrance and opens out onto a lovely shaded patio with a view of the koi pond and garden shared by other guests. There is plenty of off-street...
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    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Central Heating
    • Parking
    • Washer
    • Patio
    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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    97520, Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    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...
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    Location Information
    97520, Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Carlisle Garden Suites - Calla Suite1 / 16
    (2)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2018
    Carlisle Inn and Suites is a wonderful place to stay in Ashland. It’s centrally located to downtown and the theatres. The units are all adorable and newly remodeled. The staff...
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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
    97520, Ashland, Oregon
    Holiday Rental House - 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
    • Washer
    • Parking
    • Private Garden
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 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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    Location Information
    97520, Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • 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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    Location Information
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    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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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    Anyone in this area needing to rent a trailer should go with this company. They are wonderful. Their trailers are emmaculate and come with everything you need. They went out of...
    Reviewed 15 May 2018
    I loved driving into the campground and finding the trailer and campsite all set up and waiting for us. The trailer was super clean and well stocked with bathroom and kitchen...
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    About this property
    Vacation rental. RV Adventure. You choose favorite RV site in So. Oregon! Trailer camping is where tiny house intersects with camping; the perfect relaxing balance of re-energizing in the great outdoors and snuggling up in cozy cottage comfort! Rent a sweet recreational trailer delivered to the...
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    Location Information
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    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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    Location Information
    97520, Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Garden
    • 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
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Private Garden
    • 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...
    View all property information
    Location Information
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • 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
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
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    Payment Protection
    Amenities & Details
    • Private Garden
    • 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...
    View all property information
    Location Information
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Carlisle Garden Suites - Viola Suite1 / 14
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 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...
    View all property information
    Location Information
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
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    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • 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
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • 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
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
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    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Private Garden
    • 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
    97520, Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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