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Vacation 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.

Charming Guest House - One block from Downtown!
SUPERHOST
Entire guesthouse · 4 guests · 2 beds · 1 bath
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.
Clean, Stylish Apt w/kitchen. block from Downtown
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Clean, Stylish Apt w/kitchen. block from Downtown92½ Church Street. A private apartment with a large bedroom, full kitchen, bath with shower. Vintage styling with loads of special touches, ONE BLOCK from downtown. All the comfort of home and so close to the action. Large yard. Permitted. (Ashland City Permit: 15-237). 2020 Update: We have adopted the recommended Covid-19 Cleaning Guidelines.
Downtown Cottage - Great Views - 1 Block to OSF!
SUPERHOST
Entire cottage · 2 guests · 2 beds · 1 bath
Downtown Cottage - Great Views - 1 Block to OSF!Step out your front door and you are already downtown with a grand view! Your own private cottage 1 block from OSF, Lithia Park and downtown. COVID SANITIZED--Your health is our priority. We are taking extra precautionary measures to sanitize between each guest. Wineries, restaurants and shops are open for business and following strict safety guidelines. Enjoy the wrap around deck, amazing view, and less than 2 blocks to restaurants, shops, theaters, hiking and biking trails and Lithia Park.

Holiday rentals for every style

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Popular amenities for Ashland holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Ashland

SUPERHOST
  1. Entire guesthouse
  2. Ashland
Wood Hamlet - Picasso Suite by Downtown, w/kitchen
$155 AUD per night
SUPERHOST
  1. Entire residential home
  2. Ashland
Porscha's Hideaway Italian Upscale
$233 AUD per night
  1. Entire cottage
  2. Ashland
NEW! Sunny Cottage w/ Views, 1 Mi to Dtwn Ashland!
$210 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Ashland
Helman House Studio B
$157 AUD per night
SUPERHOST
  1. Private room
  2. Ashland
Rural Oasis, close to downtown Ashland
$105 AUD per night
SUPERHOST
  1. Entire bungalow
  2. Ashland
Penthouse Suite, easy walk to downtown.
$337 AUD per night
  1. Entire residential home
  2. Ashland
Entire residential home - Ashland Harmony Cottage
$139 AUD per night
SUPERHOST
  1. Entire guest suite
  2. Ashland
The West Wing-Stay Rogue
$172 AUD per night
SUPERHOST
  1. Private room
  2. Ashland
Lovely light filled room with porch
$121 AUD per night
SUPERHOST
  1. Entire guesthouse
  2. Ashland
Charming cottage, walk to town.
$216 AUD per night
SUPERHOST
  1. Entire guest suite
  2. Ashland
Sophisticated Downtown Suite
$183 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Ashland
Ashland Carter House, Carriage House!
$140 AUD per night