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.

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
19–26 Nov
$322 NZD per night
4.97 out of 5 average rating, 427 reviews
Guest favourite
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.
1–8 Aug
$213 NZD per night
4.91 out of 5 average rating, 311 reviews
Guest favourite
Guesthouse in Ashland
The Cedar Cottage - creekside studio
This vintage guest house is nestled along Neil Creek in the beautiful Rogue Valley. Only 4 miles (10 min drive) from the downtown plaza of Ashland you can enjoy restaurants, boutiques and the world famous Oregon Shakespeare Festival. Mt. Ashland is 30 minutes away and we are mere minutes from hiking and biking locations. We are conveniently located directly across the street from the public golf course, Oak Knoll, with easy access to I-5. Cedar Cottage is your perfect home away from home!
16–23 Dec
$201 NZD per night
4.94 out of 5 average rating, 101 reviews

Popular amenities for Ashland holiday 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 holiday rentals in Ashland

Guest favourite
Tiny home in Shady Cove
Modern Tiny House w/ Hot Tub
1–8 Sep
$237 NZD per night
4.95 out of 5 average rating, 191 reviews
Guest favourite
Home in Ashland
Coyote Moon
28 Oct – 4 Nov
$410 NZD per night
4.95 out of 5 average rating, 175 reviews
Guest favourite
Campervan/RV in Ashland
Cozy camping close to town
4–11 Apr
$89 NZD per night
4.88 out of 5 average rating, 909 reviews
Guest favourite
Cabin in Ashland
Beautiful Barndominium by Howard Prairie Lake
26 Jul – 2 Aug
$299 NZD per night
4.96 out of 5 average rating, 155 reviews
Guest favourite
Guesthouse in Ashland
JJ's Loft | Downtown | Large Deck | Kitchenette
4–11 Oct
$274 NZD per night
4.94 out of 5 average rating, 109 reviews
Superhost
Cottage in Ashland
Oak Street Studio
9–16 Dec
$278 NZD per night
4.78 out of 5 average rating, 289 reviews
Guest favourite
Guesthouse in Ashland
Modern Airy Retreat - Views, Walk to Everything
23–30 Jan
$382 NZD per night
4.94 out of 5 average rating, 117 reviews
Guest favourite
Home in Ashland
Cowslip's Rosebud Garden Suite, peaceful, central
17–24 Nov
$155 NZD per night
4.96 out of 5 average rating, 28 reviews
Guest favourite
Guesthouse in Ashland
Countryman-Fox Carriage House
25 Nov – 2 Dec
$267 NZD per night
5.0 out of 5 average rating, 49 reviews
Guest favourite
Guesthouse in Ashland
The Poets' Inspiration Cottage
5–12 May
$281 NZD per night
4.95 out of 5 average rating, 38 reviews
Superhost
Tiny home in Ashland
Ashland tiny home with view and barrel sauna
29 Jul – 5 Aug
$197 NZD per night
4.83 out of 5 average rating, 69 reviews
Guest favourite
Guest suite in Ashland
Summer’s Night Cottage 8 minute walk to Downtown
26 Jul – 2 Aug
$212 NZD per night
4.93 out of 5 average rating, 72 reviews

Quick stats about holiday 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