Vacation rentals in Ashland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Ashland

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

Guest favourite
Guesthouse in Ashland
Charming cottage, walk to town.
Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown
Nov. 20 – 27
$265 CAD per night
4.97 out of 5 average rating, 422 reviews
Guest favourite
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.
Nov. 9 – 16
$331 CAD per night
4.97 out of 5 average rating, 418 reviews
Guest favourite
Guesthouse in Ashland
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.
May 27 – Jun. 3
$216 CAD per night
4.98 out of 5 average rating, 502 reviews

Popular amenities for Ashland vacation rentals

Stay near Ashland's top sights

Lithia Park198 locals recommend
Oregon Shakespeare Festival267 locals recommend
Ashland Springs Hotel3 locals recommend
Ashland's Own Shop'n Kart38 locals recommend
Brickroom76 locals recommend
Ashland Food Co-op91 locals recommend

Other great vacation rentals in Ashland

Guest favourite
Home in Ashland
Coyote Moon
Jan. 16 – 23
$338 CAD per night
4.95 out of 5 average rating, 173 reviews
Guest favourite
Cabin in Ashland
Studio Cottage near downtown Ashland - Queen Bed!
Aug. 21 – 28
$152 CAD per night
4.94 out of 5 average rating, 207 reviews
Guest favourite
Guesthouse in Ashland
Wood Hamlet - Picasso Cottage by Downtown, kitchen
Apr. 1 – 8
$219 CAD per night
4.97 out of 5 average rating, 182 reviews
Guest favourite
Farm stay in Ashland
Kelly’s Carriage House 4 miles from Ashland
Jun. 26 – Jul. 3
$184 CAD per night
5.0 out of 5 average rating, 106 reviews
Guest favourite
Cabin in Ashland
Beautiful Barndominium by Howard Prairie Lake
Dec. 10 – 17
$247 CAD per night
4.96 out of 5 average rating, 154 reviews
Guest favourite
Home in Ashland
Swank House on Main St in Ashland
Jul. 15 – 22
$756 CAD per night
5.0 out of 5 average rating, 111 reviews
Guest favourite
Guesthouse in Ashland
The Cedar Cottage - creekside studio
Dec. 24 – 31
$166 CAD per night
4.94 out of 5 average rating, 100 reviews
Guest favourite
Camper/RV in Ashland
Cozy camping close to town
Apr. 14 – 21
$75 CAD per night
4.88 out of 5 average rating, 903 reviews
Superhost
Guesthouse in Ashland
ABBOTT'S COTTAGES- Egret
Dec. 29 – Jan. 5
$183 CAD per night
4.87 out of 5 average rating, 123 reviews
Guest favourite
Cottage in Ashland
Weisinger Winery Vineyard Cottage
Feb. 14 – 21
$362 CAD per night
4.92 out of 5 average rating, 210 reviews
Guest favourite
Guesthouse in Ashland
Modern Airy Retreat - Views, Walk to Everything
Jan. 7 – 14
$316 CAD per night
4.95 out of 5 average rating, 116 reviews
Guest favourite
Farm stay in Ashland
Kelly’s Farm 4 miles to Ashland
Aug. 20 – 27
$240 CAD per night
4.93 out of 5 average rating, 580 reviews

Quick stats about vacation rentals in Ashland

Total rentals

280 properties

Rentals with dedicated workspaces

140 properties have a dedicated workspace

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

100 properties allow pets

Family-friendly rentals

100 properties are a good fit for families

Total number of reviews

19K reviews

Destinations to explore

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