Perhaps known best for their world-renowned Oregon Shakespeare Festival, Ashland Oregon offers visitors a perfect vacation getaway filled with the arts, fine dining, spas, boutique shopping and more. This ever-increasing cosmopolitan area manages to retain its small town charm and draws visitors from around the world and nearby locales including Portland, San Francisco, and Medford Oregon. Nestled between the Cascade and Siskiyou mountains, guests of the bountiful Ashland Oregon lodging options and Medford Oregon hotels continue to be entranced by the beautiful town. Whether taking in a world-class performances, sitting in a cafe, meandering through the famed Lithia Park, or enjoying the many shops and restaurants, visitors will be inspired to return to this Hamlet town.
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Ashland Vacation Rentals
Ashland Vacation Rentals - Search Over 250,000 Listings
| Featured Rentals | Type | Beds | Baths | Sleeps | Rate | |
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Ashland - AshlandAmenities:Ski, Golf Course, Air Conditioning, TV Description:Beautiful 2 bedroom plus sitting room. Stunning walnut wood floors, brand new beds, linens, towels. Located minutes away from the center of Ashland's downtown. Enjoy the wood deck with picnic table that over looks a garden full of colors. Marble bathroom, shower with pull out seat. |
House |
2 Beds |
1 Baths |
6 People |
$65 - $150 |
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Catawba Island Cottage close to Miller Ferry - Catawba IslandAmenities:Golf Course, Kitchen, Dishwasher, Washer/Dryer, TV Description:Just like Home! A quaint Three Bedroom, Two plus Bath Ranch-style Cottage near the point of Catawba Island (off Route 53 and Porter) and within a short walking distance of the Miller Ferry to South Bass Island (Put-in-Bay) and Middle Bass Island. Perfect Island getaway nestled on a private cul-de-sac street amongst other residential cottages. |
House |
3 Beds |
2.5 Baths |
8 People |
$143 - $225 |
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Acme Suites Housing in Southern Oregon - MedfordAmenities:Golf Course, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Pets OK, TV Description:Stylish, furnished lofts ? welcome to the Acme Suites, the finest in corporate housing in Medford Oregon. Set in the increasingly trendy downtown Medford, Acme Suites corporate housing offers cutting edge style, and plush comfort for extended stay lodging. |
Condo |
2 Beds |
2 Baths |
6 People |
$77 - $77 |
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House on 1 acre of Park Like Setting!! - AshlandAmenities:Beach, Ski, Golf Course, Pool, Hot Tub, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Pets OK, TV Description:It is 10 minute drive from Ashland which has shakespeare theater and lithia park. Lots of shopping. 20 minutes from Historical downtown Jacksonville. 45 minutes to well known Applegate Valley Vineyards. Minutes from the nationally known rogue river, which has water sports and fishing and boating. 2 hours to beautiful Crater Lake and also the oregon caves. 2.5 hours to the oregon coast. Also within hours of lots of local lakes. |
House |
3 Beds |
2 Baths |
4 People |
$73 - $125 |
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Ocean View Luxury Executive Home - Coos BayAmenities:Beach, Ski, Golf Course, Pool, Hot Tub, Kitchen, Dishwasher, Washer/Dryer, TV Description:This custom home boast over 3,600 square feet of Luxury living space and will accomodate large groups, while maintaing a cozy family atmosphere. We know you will also enjoy our large recreation room, complete with pool table, game table with games & big screen TV. There is also a beautiful cozy natural gas fireplace to relax infront of while reading a great book. |
House |
4 Beds |
3.5 Baths |
11 People |
$210 - $310 |
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Southern Oregon VaCaTiOn Cottage RentaL, BeaUtifuL - AshlandAmenities:Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Smoking OK, Pets OK, TV Description:Welcome to the Blue Feather Cottage! This idyllic and peaceful setting is located just 4 short miles from the stage of the World Famous Outdoor Elizabethan Theatre and 25 minutes to the big mountain's ski base. Providing an ambiance only a renovated 112-year-old general store can offer, our family-friendly cottage boasts comfortable, upgraded, rich interiors. |
House |
2 Beds |
1 Baths |
5 People |
$68 - $139 |
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Summer Beach House - Rockaway BeachAmenities:Beach, Golf Course, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning Description:This newly-built, two-story, three bedroom, two-bath home is located in a quiet neighborhood one mile from Rockaway Beach, east of the 101. Our home features a peaceful and serene environment with new appliances, a cozy, efficient kitchen and living room, as well as very comfortable bedrooms all with individualized heating controls. The house is newly furnished with three new queen beds and a futon for additional sleep space ( or a nice relaxing couch). |
House |
3 Beds |
2 Baths |
7 People |
$90 - $130 |
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Hood River,OR-4 bedrm2ba.Nature Retreat-sleeps 9 - Hood RiverAmenities:Beach, Ski, Pool, Kitchen, Dishwasher, Air Conditioning, TV Description:July and August ONLY-Darling Dollhouse in spacious country setting-close to town (by the Hood River-8 miles to town) 1/2 drive to Mt. Hood-year round skiinng/snowboarding at Timberline Lodge. still available for Labor day weekend! Relax into this peaceful 4 Bedroom/ 2 Bath retreat in the country and only 10 minutes to Hood River with gorgeous view over the Hood River valley. completely charming newly renovated adorable farmhouse. |
House |
4 Beds |
2 Baths |
9 People |
$97 - $186 |
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New Vacation Home, OLD MILL DISTRICT - BendAmenities:Ski, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, TV Description:Brand New Home in Southwest Bend. Close to Old Mill District Dining, Shops, Theaters and Mt. Bachelor. Spacious bedrooms, gas fireplace, granite counters in kitchen, large 2 car garage and more. Holiday Prices Subject to Change |
House |
3 Beds |
2.5 Baths |
8 People |
$71 - $175 |
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Ashland's Best Executive Vacation Home - AshlandAmenities:Beach, Ski, Golf Course, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, TV Description:Come to Ashland in September and stay 3 mid- week nights (WED, TUES, THURS) for only $600! You Save $150. Weather is great and the theaters are still in full swing. |
House |
3 Beds |
2.5 Baths |
6 People |
$94 - $250 |
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