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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The Frontier Cabin at Lakewoods Village - Klamath FallsAmenities:Ski, Kitchen, Dishwasher, Washer/Dryer, TV Description:Lakewoods Village is a less than 45 minute drive to Medford, Ashland, and/or Klamath Falls, OR. The Frontier is a cozy 673 sq. ft. cabin centered in Lakewoods Village between the trees of the Winema National Forest in the Southern Oregon Cascade Mountains. The bedroom is an upstairs loft which overlooks the living room and dining room. |
House |
1 Beds |
1 Baths |
5 People |
$102 - $175 |
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Beautiful Newly Remodeled Spacious Home - GearhartAmenities:Beach, Kitchen, Dishwasher, Washer/Dryer, TV Description:This sophisticated Gearhart beach house sits on a large private lot with a big back yard. The house is conveniently located on the beach side of Marion St. three blocks south of the Gearhart golf course and clubhouse ... and is just a short two block walk to the beach! We have recently remodeled the entire home with all modern conveniences but traditional beach charm exists throughout. |
House |
4 Beds |
3 Baths |
12 People |
$300 - $350 |
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The Rockhaven Cabin at Lakewoods Village - Klamath FallsAmenities:Ski, Golf Course, Hot Tub, Kitchen, Dishwasher, Washer/Dryer, TV Description:Lakewoods Village is a less than 45 minute drive to Medford, Ashland, and/or Klamath Falls, OR. The Rockhaven is a serene 2,520 sq. ft. Northwest style cabin encompassed by the trees of the Winema National Forest in the Southern Oregon Cascade Mountains. This home boasts 3 Master Suites. The downstairs Master Suite includes a fireplace, sliding glass doors to a covered deck, walk-in closet, and master bathroom with soaker tub, full shower, and double sinks. |
House |
3 Beds |
3.5 Baths |
10 People |
$257 - $375 |
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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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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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HOCKING HILLS - Hickory Grove Lake View Cabin - Hocking HillsAmenities:Beach, Ski, Pool, Kitchen, Dishwasher, Air Conditioning, TV Description:This cabin is set on 8 acres with its own private pond right in the heart or Hocking Hills with 3 Bedrooms, 2 Bathrooms, Kitchen with all stainless steel appliances, six person Hot Tub on a Large covered deck overlooking the stocked pond, Fire Pit, Central Air, state of art Water Treatment System, to many more amenities to mention... |
House |
3 Beds |
2 Baths |
6 People |
$135 - $200 |
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WALK to Downtown Ashland's from this New Home! - AshlandAmenities:Ski, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning Description:Walk just 2-3 blocks to all that beautiful downtown Ashland has to offer! World class galleries, restaurants, pubs, museums, cafes, groceries, endless shops, and of course the world renowned Shakespeare Festival! Park your car in your garage - and just LEAVE it there |
House |
3 Beds |
2 Baths |
8 People |
$77 - $190 |
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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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The Prospector Cabin at Lakewoods Village - Klamath FallsAmenities:Ski, Golf Course, Hot Tub, Kitchen, Dishwasher, Washer/Dryer, TV Description:Lakewoods Village is a less than 45 minute drive to Medford, Ashland, and/or Klamath Falls, OR. The Prospector is a beautiful 2,481 sq. ft. Northwest style cabin nestled between the trees of the Winema National Forest in the Southern Oregon Cascade mountains. Master Suite includes a corner propane fireplace, sliding glass doors to the private covered deck, walk-in closet, and master bathroom with jetted tub, full shower, and double sinks. |
House |
3 Beds |
2 Baths |
14 People |
$257 - $375 |
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