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Holiday rentals in Ashland

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Top-rated holiday rentals in Ashland

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

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  1. Entire guest house
  2. Ashland
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.

SUPERHOST
  1. Entire home
  2. Ashland
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.

SUPERHOST
  1. Entire guest suite
  2. Ashland
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.

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Other great holiday rentals in Ashland

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  1. Entire cabin
  2. Ashland
The Ashland Farm Cabin
  1. Entire guest suite
  2. Ashland
Perk's home away from home
SUPERHOST
  1. Entire guest suite
  2. Ashland
The West Wing-Stay Rogue
SUPERHOST
  1. Private room
  2. Ashland
Peaceful & Private Bedroom and kitchenette!
SUPERHOST
  1. Private room
  2. Ashland
Lovely light filled room with porch
SUPERHOST
  1. Entire cottage
  2. Ashland
Downtown Cottage - Great Views - 1 Block to OSF!
  1. Entire guest house
  2. Ashland
Historic carriage house close to downtown Ashland
SUPERHOST
  1. Entire guest house
  2. Ashland
The Cedar Cottage - creekside studio
SUPERHOST
  1. Private room
  2. Ashland
Wood Hamlet - Noble Forest Room Private by DownTn
SUPERHOST
  1. Entire guest house
  2. Ashland
B Street Cottage
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  1. Entire guest house
  2. Ashland
Charming cottage, walk to town.
SUPERHOST
  1. Entire guest house
  2. Ashland
East Main Downtown Bungalow