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Ashland Vacation Rentals

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    Travelers to Ashland are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 15
    5 of 5 bubbles (21) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (2) Excellent
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    5 of 5 bubbles (10) Excellent
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    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Mountain Views
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    About this property
    A “lake cabin” vacation can become a reality at Hyatt Lake Resort, approximately 22 miles east of Ashland on Rt. 66. The forest surrounds the cabin, which is located at “Campers’ Cove.” From the front deck you can BBQ while viewing the lake, enjoy the Jacuzzi or just sit and watch the eternity of... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 bubbles Reviewed October 12, 2016
    Being campers, typically, we felt like we were royalty in the woods. There was every kind of dish necessary to prepare our meals, as well as a wonderful BBQ, and wonderfully cozy...
    5 of 5 bubbles Reviewed September 7, 2016
    The resort at campers cove was such a wonderful place to stay, the cabins are so comfortable and nice just like being at home. We had a wonderful visit with the owner and his...
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    1 / 10
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 bubbles Reviewed March 4, 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 without...
    5 of 5 bubbles Reviewed July 10, 2014
    The High Street Cottage is our new favorite place to stay in Ashland. The cottage and grounds were beautifully maintained and thoughtfully stocked with coffee, tea, cooking...
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    1 / 20
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 bubbles Reviewed September 24, 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...
    5 of 5 bubbles Reviewed May 6, 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
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    1 / 23
    4.5 of 5 bubbles (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Private cottage apartment with full kitchen and living area adjacent to family home. Covered porch and garden area to enjoy. Less than 15 minutes to Shakespeare Festival and downtown Ashland. Fresh eggs, local bread, jam, 1/2 and 1/2, milk and butter are stocked in fridge. There is also Nespresso,... View all property information
    Location Information
    Ashland, Oregon 97520
    4 of 5 bubbles Reviewed May 8, 2016
    This cozy cottage in a ranch setting was also a nice getaway from town. Organic eggs, local bread, butter and jam supplied by our host made us feel welcome and provided breakfast...
    5 of 5 bubbles Reviewed March 31, 2015
    An ideal cottage in a country setting, 15 minutes from Oregon Shakespeare Festival. It's the little things that make a big difference to me: friendly, flexible host; comfy bed...
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    1 / 12
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
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    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 bubbles Reviewed August 8, 2015
    We have been staying at this property once a year for over 10 years, and we can hardly wait to return the next year. This rental and it's adjacent cottage are beautifully...
    5 of 5 bubbles Reviewed July 23, 2015
    We stayed three days at Lori Lane. There were four of us and it suited us very well. It is walking distance to downtown and the OSF. We ate our breakfasts and a couple of other...
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    1 / 15
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Yard
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    About this property
    Newly remodeled for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic local restaurants. Guests have access to private off-street parking and fully stocked... View all property information
    Location Information
    Ashland, Oregon 97520
    4 of 5 bubbles Reviewed July 23, 2014
    I took my 86 year old mother with me to visit Ashland. The cottage was very clean and cozy and my mom was delighted. There is no real living or dining space inside but the outdoor...
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    1 / 25
    5 of 5 bubbles (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... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 bubbles Reviewed July 2, 2016
    Perfectly furnished for our party of four adults; perfectly stocked kitchen; perfect front yard for dining al fresco and watching deer go by; perfect neighborhood for daily...
    5 of 5 bubbles Reviewed August 24, 2015
    Great location for walking to theatres as well as restaurants and shopping in Ashland. Great space for two couples to be separate or to be together. Front porch is a...
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    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Enjoy a free bottle of wine... let us know, red or white... and free admission to one of our summertime concerts (if it coincides with your stay). Nestled on the slopes of Grizzly Peak, less than ten minutes from Downtown Ashland sits our second floor studio cottage! A 600sqft+ studio cottage... View all property information
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    Ashland, Oregon 97520
    1 / 23
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 17
    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,... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Waterfront
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    • Mountain Views
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Just eighteen miles east of Ashland and POCKET VIEWS OF HYATT LAKE! Welcome to your Hyatt Lake Cabin, with a BBQ, and a large deck overlooking the forest, and pocket views of Hyatt Lake. It's just a few minute walk down to the water! The master bedroom has a queen size bed, and the loft has two... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Ashland, Oregon 97520
    1 / 8
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from theaters, Plaza and Downtown. Let this charming, historic home fill you with a sense of well-being and luxury. There are two bedrooms, each with a queen bed, and a... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 7
    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... View all property information
    Location Information
    Ashland, Oregon 97520
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Ashland, Oregon 97520
    1 / 20
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
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    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... View all property information
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    Ashland, Oregon 97520
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Second Spring Property<BR>We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014.<BR>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... View all property information
    Location Information
    Ashland, Oregon 97520
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    1 / 13
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Ashland, Oregon 97520
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Ashland, Oregon 97520
    1 / 16
    5 of 5 bubbles (17) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    APRIL SPECIAL 3 NIGHTS 15% OFF 4 NIGHTS 25% OFF Welcome to the Artycottage nestled in the Cascade foothills, minutes from downtown Ashland, Oregon, home of the Oregon Shakespeare Festival and Saydah Design. All of the work in the Artycottage is made by Saydah Design and can be... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 bubbles Reviewed August 13, 2016
    We had a remarkable time here as we celebrated grandma's 80th birthday with 3 generations of daughters. The pictures did not prepare us for the utter beauty of the cottage and...
    5 of 5 bubbles Reviewed September 14, 2015
    What really sets this cottage apart from many you may have rented is that the owners have hand crafted and built every inch of the inside and outside. It is artistry and...
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    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Welcome to the Blue Hyacinth in Blossom View Cottages. Walk to downtown and OSF or sit back and relax at the Blue Hyacinth, part of Blossom View Cottages. This is a luxurious and comfortable home in Ashland's historic railroad district. Downtown Ashland, the theaters, and galleries on A-Street are... View all property information
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    Ashland, Oregon 97520
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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... View all property information
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    Ashland, Oregon 97520
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    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. <BR><BR>We offer boating, hiking trails throughout the area. We have wineries that offer award... View all property information
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    Ashland, Oregon 97520
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Ashland, Oregon 97520
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    STAY <BR>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... View all property information
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    Ashland, Oregon 97520
    1 / 10
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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... View all property information
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    Ashland, Oregon 97520
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Ashland, Oregon 97520
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Ashland, Oregon 97520
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Ashland, Oregon 97520
    1 / 31
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Have a truly memorable trip to Oregon when you stay at this gorgeous 4-bedroom, 3-bathroom Ashland home, which sleeps 13. Enjoy the best of outdoor living with a private fishing pond and plenty of patio space with spectacular views! This Ashland vacation rental home is an ideal accommodation... View all property information
    Location Information
    Ashland, Oregon 97520
    5 of 5 bubbles Reviewed April 19, 2017
    Our family thoroughly enjoyed our stay at this stunning vacation cabin located in an area that provided plenty of privacy. The Guest Contact person, Eliasar, who greeted us upon...
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    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Ashland, Oregon 97520
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    1 Bedroom, 2 Bathrooms, Sleeps 5 | Quick View
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    Ashland, Oregon 97520
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Just a quick five minutes from Downtown Ashland! Views of mountains, sheep, and chickens can be enjoyed from YOUR private deck, with (seasonal) hops, grapes and blackberries growing right outside your bedroom window This spacious modern suite is bright and comfortable, has a private entrance,... View all property information
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520 2650
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    THE GARDEN SUITE IS A CHARMING TWO BEDROOM, 2 FULL BATH COTTAGE THAT COMFORTABLY WELCOMES 5 GUESTS. 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 and has... View all property information
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    Ashland, Oregon 97520
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    About this property
    Located in the East Ashland countryside, and exactly three miles from the famous Downtown Ashland Plaza and Oregon Shakespeare Festival, our cottage has it all! Enjoy the gardens, the mountain views, and the artwork of local Artist, Michael Gibson. Enjoy the Art and Gardens of one of Ashland's... View all property information
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    Ashland, Oregon 97520
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    Location Information
    Ashland, Oregon 97520
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    Ashland Vacation Rentals

    Are you looking for the perfect vacation 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 vacation 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 vacation 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 vacation 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.