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Ashland Vacation Rentals

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    Travellers to Ashland are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 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 3 Quick View
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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
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    • Private Garden
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    • Mountain Views
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    Pet friendly
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    Smoking allowed
    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Perfect vacation cottage1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Just a stone's throw to the plaza, a licensed one-bedroom vacation rental suite is tucked behind one of Ashland's charming craftsman-style bungalows. Your private gated entrance, located behind the house, opens onto a peaceful garden and quaint patio - a wonderful place to enjoy morning coffee and...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • Washer
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in the West Bedroom, a queen bed...
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    Ashland, Oregon 97520
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Air Conditioning
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Outdoor Dining Area
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    • Grill
    • Shared Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very beautiful modern unique property. Two bedrooms, sitting room/kitchenette all custom designed, Italian fixtures, exquisite cherry wood floors, marble bathroom, wireless internet, cable TV, HBO/ Showtime, central air/heater, and a stunning view of the private back garden. All you...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Mountain Views
    • Porch
    • Outdoor Dining Area
    • Shared Garden
    • Parking
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    STAY Overlooking beautiful meadows, the light filled studio sleeps up to six with two queen beds in the loft rooms and a double sofa-bed downstairs. The Farrmhouse Studio also features a wood stove and a full kitchen stocked with dry goods. On-Farm Store has all our meats, sausages, eggs and milk...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, historic, fully renovated home with four bedrooms, three full baths and a fabulous welcoming front porch. Can be rented with Garden Suite, a 2 bedroom, 2 full bath house that sleeps five. Perfect location for your visit to Ashland. Historic Railroad District is situated between two...
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    Ashland, Oregon 97520
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
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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
    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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    Smoking allowed
    About this property
    A corner room filled with filtered light from shuttered windows, this room is guarded by two ancient holly trees with red berries. The door opens onto an outside dining area on the deck, enjoyed by all who come. This room also has a kitchenette and a spacious bath with a jetted tub. The Carlisle...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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 Garden
    • Air Conditioning
    • Wi-Fi
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Smoking allowed
    About this property
    A sunny cheerful room on the south side, this suite's soft green wainscoting, and modern furnishings create a relaxing environment. A king/twin bed, an eating nook in the corner, and the spacious private deck area just outside the door make it the choice of many. A kitchenette and sunny private...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    A high queen bed dominates the space, which gets diffused light from a skylight and windows on three sides. A spacious bathroom features a clawfoot tub, a separate tiled shower, stained glass window and another wonderful skylight. The Carlisle Garden Suites has 9 unique rooms in three buildings...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    You'll think you've arrived at your Grandmother's when you walk on to the Calla Suite's front porch, replete with a swing and wicker furniture. Pleasingly decorated in relaxing hues, the room is furnished with an 1850's Eastlake piece built in Portland – a queen bed.. A kitchenette and eating area...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Smoking allowed
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    Visitors to Rose haven't wanted to leave this second-story hideaway with its magical deck overlooking Mt. Grizzly. Curl up on the daybed in the sitting room with a fire in the gas fireplace to watch a movie or be tempted by the giant Jacuzzi in the luxurious bathroom. The bedroom, which can be a...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
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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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    A high ceiling with fan and marvelous light throughout the day give this room a sense of comfort and elegance. Decorated with lavender and turquoise, it has king/twin beds, kitchenette, two-person Jacuzzi tub and opens on to the back deck that overlooks our quiet gardens. The Carlisle Garden...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Wi-Fi
    • Mountain Views
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    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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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    This is the largest room of the suites and has a single bed with trundle as well as a king/twin. Surrounded by mature trees and fragrant jasmine vine, this room offers a palette of Ashland summer sky blues. A kitchenette, walk-in multi-headed luxury shower for two and the deck overlooking a...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    One of our new luxury suites in the middle of the garden, Iris features a cozy day bed in the sitting room with fireplace and television, as well as a full kitchen and eating area. Dappled light from glass brick windows cascades over the king bed (which can also be twins). Mexican ceramics...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Best Location, Impeccable Style and Ultimate Comfort1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Our cottage is where you want to stay in Ashland! From its fantastic location to its custom craftsman design to the overall comfort, you'll be delighted with your choice! Just 3 level blocks from the downtown Ashland Plaza and Shakespeare festival. Along with clean, quality and location,...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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    • Washer
    • Skiing: Property Is In A Ski Resort
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    • Shared Garden
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our property is located in the quaint Shakespearean town of Ashland, Oregon. The town has exceptional and award winning contemporary plays and the largest Shakespearean theater in the United States. We offer boating, hiking trails throughout the area. We have wineries that offer award winning...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Sauna
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Emigrant Creek Guest Lodge above Emigrant Lake. Gorgeous views and water sourced from volcanic healing mineral springs where mountains adjoin volcanism. Nearby are mineral hot/cold springs used by Native people to treat and for ceremonies. Very restorative. The Lodge water has been...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Beautiful new private apartment at the historic Hargadine House, one block from Ashland's best theaters and restaurants. Features a plush king bed, soaking tub, radiant tile heat in bathroom, walk in shower, balcony, view, high ceilings, modern appliances, quality linens, kitchen. You will be...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Washer
    • Terrace
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    • Skiing: Property Is In A Ski Resort
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    • Sauna
    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book an unforgettable natural getaway to 'Enchanted Rabbit Mountain,' a 2-bedroom, 1.5-bath vacation rental on a wildlife sanctuary in Ashland. This 1,692-square-foot cabin is a special, sacred place inside the Cascade Siskiyou National Monument, where the historic Highway 66 and Pacific Crest...
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    Ashland, Oregon 97520
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    A high ceiling with skylight, a spacious bedroom with king/twin beds done in soft greens, an art deco flavor and a wonderful sense of privacy give guests a taste of being removed from the fray. This room is a favorite of dog lovers with its glassed-in porch. A kitchenette and private bath with...
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    Ashland, Oregon 97520
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Patio
    • Internet Access
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    • Cable/satellite TV
    • Shared Garden
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    • Mountain Views
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located in the heart of Ashland. Only 2 blocks from Downtown. Enjoy the open Garden and Great location to all Restaurants, Shops, Theaters and Local Sporting Events. We are 3 blocks from University of Southern Oregon. Full Kitchen, Bedroom/Queen, Wall mounted reading lamps and TV. The...
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    Ashland, Oregon 97520
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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