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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.

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Autumn on Pine Street! 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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Spacious Historic Downtown Home, spend the spring!

Available March 2, 2022! 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. Very 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. Quiet! Includes all utilities, Wi-Fi, OFF STREET PARKING! No pets or smoking.

$60 per night
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Ashland Backyard Garden Studio

Charming garden view studio one block above the University. Kitchenette with small fridge, microwave, hotplate, toaster oven, and coffee maker, all pots and pans. Queen bed, cable TV and WiFi. Bathroom with shower. Sleeps 2, with futon for 3rd guest.

$38 per night

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Other great vacation rentals in Ashland

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Peaceful & Private Bedroom and kitchenette!
$68 per night
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  2. Ashland
The Ashland Farm Cabin
$83 per night
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  1. Private room
  2. Ashland
Lovely light filled room with porch
$90 per night
  1. Entire guest suite
  2. Ashland
Perk's home away from home
$50 per night
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  2. Ashland
Charming cottage, walk to town.
$164 per night
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  1. Private room
  2. Ashland
Wood Hamlet - Noble Forest Room Private by DownTn
$66 per night
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  1. Entire cottage
  2. Ashland
Downtown Cottage - Great Views - 1 Block to OSF!
$146 per night
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  1. Entire guest suite
  2. Ashland
The West Wing-Stay Rogue
$130 per night
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  2. Ashland
B Street Cottage
$109 per night
  1. Entire guesthouse
  2. Ashland
Historic carriage house close to downtown Ashland
$115 per night
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JJ's Loft | Downtown | Large Deck | Kitchenette
$139 per night
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  2. Ashland
Coyote Moon
$200 per night