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Cottage vacation rentals in Ashland

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Top-rated cottage rentals in Ashland

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

Guest favorite
Cottage in Ashland
Charming very well appointed cottage !
The Farm Cottage is a renovated former horse hotel. It retains the charm of its former use yet is well appointed and updated for comfort & convenience. The cottage overlooks a pasture with 2 barns with the Siskiyous beyond to the south & the Ashland, Grizzly Peak Hills to the east. We are only 2 easy miles from downtown Ashland with multiple wineries close by. There is hiking, swimming at Emigrant Lake nearby as well. If quiet is what you are looking for, the cottage will meet all your needs.
$106 per night
Guest favorite
Cottage in Phoenix
The Pear Cottage Where city and country life meet
This is on a 42 acre family farm that dates back to 1910. Beautiful, quiet and very relaxing. We think you will love this completely renovated living space. With a private deck off each bedroom with lots of outdoor seating. Our home is just minutes away from Ashland Shakespeare and Jacksonville Britt Festivals. We are surrounded by the most breathtaking wineries, Skiing, Hiking the Pacific Crest Trail, Crater Lake and lots more. Enjoy looking out of the beautiful hay field and having coffee.
$100 per night
Guest favorite
Cottage in Ashland
Victorian Garden Carriage House
You will wake in the trees, to the soft prospects of the forested Siskiyou mountains to the west. You'll discover enchanting views at every window, from city streets to a quiet English garden and pond. You are only a few steps from Ashland Plaza, yet the retreat-like environment we offer to all our guests requires that no incense, smoking, vaping or pets are allowed in the Carriage House. The City of Ashland has authorized the Carriage House. Our City Planning Action Number is PA-2013-01701.
$150 per night

Popular amenities for Ashland cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Gold Hill
Hot Tub w/ River Views / Private Patio / Spacious
$145 per night
Guest favorite
Cottage in Jacksonville
🥂The Applegate Spa🥂
$187 per night
Guest favorite
Place to stay in Jacksonville
Britt Cottage Perfect Location
$157 per night
Guest favorite
Cottage in Ashland
Weisinger Winery Vineyard Cottage
$225 per night

Pet-friendly cottage rentals

Guest favorite
Cottage in Medford
Stunning Private Orchard Property
$139 per night
Guest favorite
Cottage in Medford
Efficient, clean, pet-friendly 2 bed/bath cottage
$98 per night
Guest favorite
Cottage in Central Point
Farm Cottage 1/2 Mile Outside Jacksonville
$75 per night
Guest favorite
Cottage in Ashland
The Red Dragon House
$169 per night
Guest favorite
Cottage in Jacksonville
Cozy Cottage on Riverfront Farm near Vineyards
$99 per night
Superhost
Cottage in Phoenix
Remodeled 600 square foot apartment
$77 per night
Guest favorite
Cottage in Medford
Pet Friendly by SuperHost
$78 per night
Guest favorite
Cottage in Central Point
Charming Cottage, Near Rellik & Jville. Pets ok!
$109 per night
Superhost
Cottage in Ashland
ArtyCottage built by a custom furniture maker.
$195 per night
Guest favorite
Cottage in Grants Pass
The Cherry Cottage with built in pool
$185 per night
Guest favorite
Cottage in Jacksonville
Rider House
$199 per night
Guest favorite
Cottage in Gold Hill
Rogue Rivers Edge | 1 BR Fishing Inspired Cottage
$82 per night

Private cottage rentals

Guest favorite
Cottage in Grants Pass
Applegate Wine Country cottage!
$71 per night
Guest favorite
Cottage in Jacksonville
Wisteria Cottage
$174 per night
Guest favorite
Cottage in Ashland
Lovely cottage near park and town!
$56 per night
Guest favorite
Cottage in Ashland
Ashland's new vacation rental
$207 per night
Guest favorite
Cottage in Jacksonville
Lily Pad/#1 Best Location/Full Kitchen/Luxurious
$169 per night
Guest favorite
Cottage in Jacksonville
Cottage B with Private Patio
$179 per night
Superhost
Cottage in Central Point
Beautiful cottage w/pool in bamboo forest
$182 per night
Superhost
Cottage in Grants Pass
‘Quigley's River Pass’ Cottage w/ Private Deck!
$106 per night
Guest favorite
Cottage in Shady Cove
Rogue River Retreat
$150 per night
Guest favorite
Cottage in Phoenix
FARMHOUSE COTTAGE
$135 per night
Guest favorite
Cottage in Medford
Capital House *Pool* Great Location* Quiet Getaway
$350 per night
Guest favorite
Cottage in Jacksonville
Historic Bradshaw House!
$165 per night

Quick stats about cottage rentals in Ashland

Total rentals

10 properties

Local attractions

Lithia Park, Oregon Shakespeare Festival, and Ashland Springs Hotel

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Total number of reviews

1.9K reviews

Nightly prices starting at

$60 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland
  6. Cottage rentals