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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.

Charming Guest House - One block from Downtown!
SUPERHOST
Entire guest house · 4 guests · 2 beds · 1 bathroom

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.

The Ashland Farm Cabin
SUPERHOST
Entire cabin · 2 guests · 1 bed · 1 bathroom

The Ashland Farm CabinCome stay on our beautiful farm just minutes from downtown Ashland. Enjoy gorgeous views of the East foothills and Mt. Ashland to the West.

Charming & private cottage w/ patio near downtown
SUPERHOST
Entire guest house · 2 guests · 1 bed · 1 bathroom

Charming & private cottage w/ patio near downtownCozy and charming detached guest cottage near downtown Medford. Private parking for one car, independent access, and your own little garden patio with BBQ. Located off the main road in a nice quiet neighborhood. Non-smoking only. The ambiance is relaxing and peaceful with a comfy full-sized bed with down comforter. There is a small kitchenette with mini fridge, toaster, hot water kettle, and microwave. Easy access to downtown and I-5. ***The window A/C has been removed for the season***

Holiday rentals for every style

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Popular amenities for Ashland holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Ashland

SUPERHOST
  1. Farm stay
  2. Ashland
Cozy Private Apartment on Farm
SUPERHOST
  1. Entire guest house
  2. Ashland
Ashland Guest House; private, retreat-like
SUPERHOST
  1. Entire cottage
  2. Ashland
MAY SPECIAL! Stunning New Home. Walk Everywhere!
SUPERHOST
  1. Entire cottage
  2. Phoenix
Modern Getaway on Sunflower Farm
SUPERHOST
  1. Entire flat
  2. Ashland
Victorian Garden Carriage House
SUPERHOST
  1. Entire flat
  2. Ashland
Clean, Stylish Apt w/kitchen. block from Downtown
SUPERHOST
  1. Entire guest house
  2. Ashland
Charming cottage, walk to town.
SUPERHOST
  1. Entire cottage
  2. Ashland
Downtown Cottage - Great Views and Location!
SUPERHOST
  1. Entire guest suite
  2. Ashland
Summer's Night Cottage (1 BR Downtown Suite)
SUPERHOST
  1. Entire guest suite
  2. Ashland
Sophisticated Downtown Suite
SUPERHOST
  1. Entire house
  2. Ashland
Coyote Moon
SUPERHOST
  1. Entire guest house
  2. Medford
Eco-Tiny House in SE Medford

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