Vacation rentals in Ashland

Find and book unique accommodation on Airbnb

Top-rated accommodation in Ashland

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

Guest favourite

Apartment in Ashland

4.94 out of 5 average rating, 255 reviews

Mexico Apartment at Wood Hamlet, by Downtown

The Wood Hamlet Mexico Apartment is a delightful space filled with color and culture. A short walk to town, 72-acre park & the theaters. Feel the welcoming warmth of the hand-crafted Mexican decor. Basement unit but with lots of windows and light. (low ceiling) Kitchen, with top of the line induction burner, fridge, microwave..., full bath, W/Dryer, work area... Wi-fi. Beautiful, garden with sitting areas & swimming pond. Private parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES

14–21 May

$244 NZD per night
Guest favourite

Guesthouse in Ashland

4.97 out of 5 average rating, 427 reviews

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

$328 NZD per night
Guest favourite

Cottage in Phoenix

4.91 out of 5 average rating, 310 reviews

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.

8–15 Apr

$191 NZD per night

Popular amenities for Ashland accommodation

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 accommodation in Ashland

Guest favourite

Campervan/RV in Ashland

4.88 out of 5 average rating, 913 reviews

Cozy camping close to town

28 Apr – 5 May

$92 NZD per night
Guest favourite

Farm stay in Ashland

5.0 out of 5 average rating, 116 reviews

Kelly’s Carriage House 4 miles from Ashland

7–14 Jun

$265 NZD per night
Guest favourite

Home in Ashland

4.95 out of 5 average rating, 178 reviews

Coyote Moon

14–21 Jan

$417 NZD per night
Guest favourite

Cabin in Ashland

4.96 out of 5 average rating, 155 reviews

Beautiful Barndominium by Howard Prairie Lake

8–15 Dec

$305 NZD per night
Guest favourite

Home in Ashland

4.96 out of 5 average rating, 238 reviews

Secluded Forest Log House 15 minutes to Ashland

29 Nov – 6 Dec

$320 NZD per night
Guest favourite

Farm stay in Ashland

4.94 out of 5 average rating, 589 reviews

Kelly’s Farm 4 miles to Ashland

13–20 Aug

$294 NZD per night
Guest favourite

Guesthouse in Ashland

4.94 out of 5 average rating, 109 reviews

JJ's Loft | Downtown | Large Deck | Kitchenette

13–20 Feb

$279 NZD per night
Guest favourite

Guest suite in Ashland

4.93 out of 5 average rating, 73 reviews

Summer’s Night Cottage 8 minute walk to Downtown

27 Oct – 3 Nov

$204 NZD per night
Guest favourite

Home in Ashland

4.92 out of 5 average rating, 25 reviews

Cowslip's Love-In-Idleness Garden En Suite

13–20 Dec

$143 NZD per night
Guest favourite

Guesthouse in Ashland

5.0 out of 5 average rating, 51 reviews

Countryman-Fox Carriage House

30 Jan – 6 Feb

$251 NZD per night
Superhost

Tiny home in Ashland

4.83 out of 5 average rating, 70 reviews

Ashland tiny home with view and barrel sauna

11–18 Aug

$201 NZD per night
Guest favourite

Home in Ashland

5.0 out of 5 average rating, 19 reviews

The Aloha House - Hot Tub - Pool

23–30 Nov

$727 NZD per night

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