Ashland vacation rentals

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Top-rated vacation rentals in Ashland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Home in Ashland
Available! Spacious Historic Downtown Home!
Available October 17-January 29th and March through spring, 2023! This is a monthly rental. VERY LARGE (1,190 sq ft) historic home in downtown location in fun neighborhood, two blocks from Festival! Open floor plan, ONE level! Furnished. Wood floors. LARGE bedroom with bay window, QUEEN antique bed. Dining room with lovely lighting. Claw-foot bathtub with overhead shower. Office, game table, utility porch, laundry room. Includes all utilities, Wi-Fi, OFF STREET PARKING! No pets or smoking.
$60 per night
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Guesthouse in Ashland
Charming Guest House - One block from Downtown!
This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.
$109 per night
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Guesthouse in Ashland
Cozy Cottage near Town!
This is a 30 day minimum listing. Stay on the BEST STREET in Ashland, a 4 minute STROLL to Lithia Park, and 6 minutes to TOWN and the SHAKESPEARE Festival. The bedroom has a double bed with luscious sheets There is a shower and tub, hand-made soaps and lots of fresh towels. The kitchen is fully STOCKED with everything you might need. The living room is filled with light, comfortable seating, and a bay window with table and chairs for RELAXING after a busy day. No smoking or pets.
$56 per night
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Stay near Ashland's top sights

Photo of North Mountain Park
North Mountain Park4 locals recommend
Photo of Louie's of Ashland
Louie's of Ashland18 locals recommend
Photo of Oregon Cabaret Theatre
Oregon Cabaret Theatre50 locals recommend
Photo of Weisinger Family Winery
Weisinger Family Winery15 locals recommend
Photo of Southern Oregon University
Southern Oregon University29 locals recommend
Photo of Oregon Shakespeare Festival
Oregon Shakespeare Festival267 locals recommend

Other great vacation rentals in Ashland

Rental unit in Ashland
Clean, Stylish Apt w/kitchen. block from Downtown
$109 per night
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Guesthouse in Ashland
Charming cottage, walk to town.
$120 per night
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Rental unit in Ashland
The West Wing
$121 per night
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Bungalow in Ashland
Crow's Cottage- Unwind in the calm. EV charger.
$141 per night
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Farm stay in Ashland
Kelly’s Farm 4 miles to Ashland
$95 per night
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Cabin in Ashland
The Ashland Farm Cabin
$83 per night
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Guesthouse in Ashland
ABBOTT'S COTTAGES- Egret
$110 per night
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Cottage in Ashland
Downtown Cottage - Great Views - 1 Block to OSF!
$139 per night
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Cottage in Ashland
Charming very well appointed cottage !
$116 per night
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Cabin in Ashland
Private Cottage Cabin Getway near Ashland Plaza!
$82 per night
Private room in Ashland
Wood Hamlet - E. Gorey Room, Private by Downtown
$60 per night
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Private room in Ashland
Peaceful & Private Bedroom and kitchenette!
$67 per night
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