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.

Guest favourite

Flat 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

5–12 Jul

$169 SGD per night
Guest favourite

Guest house 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

15–22 Feb

$230 SGD 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.

26 Aug – 2 Sep

$144 SGD per night

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

Campervan/Motorhome in Ashland

4.88 out of 5 average rating, 912 reviews

Cozy camping close to town

28 Apr – 5 May

$73 SGD per night
Guest favourite

Home in Ashland

4.95 out of 5 average rating, 178 reviews

Coyote Moon

14–21 Jan

$311 SGD per night
Guest favourite

Farm stay in Ashland

5.0 out of 5 average rating, 115 reviews

Kelly’s Carriage House 4 miles from Ashland

7–14 Jun

$201 SGD per night
Guest favourite

Home in Ashland

4.96 out of 5 average rating, 238 reviews

Secluded Forest Log House 15 minutes to Ashland

22–29 Dec

$240 SGD 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

$242 SGD per night
Guest favourite

Farm stay in Ashland

4.94 out of 5 average rating, 589 reviews

Kelly’s Farm 4 miles to Ashland

6–13 Sep

$226 SGD per night
Superhost

Cottage in Ashland

4.78 out of 5 average rating, 289 reviews

Oak Street Studio

25 Dec – 1 Jan

$197 SGD per night
Guest favourite

Guest house in Ashland

4.94 out of 5 average rating, 109 reviews

JJ's Loft | Downtown | Large Deck | Kitchenette

19–26 Dec

$194 SGD 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

1–8 Oct

$139 SGD per night
Guest favourite

Guest house in Ashland

5.0 out of 5 average rating, 51 reviews

Countryman-Fox Carriage House

10–17 Nov

$184 SGD per night
Superhost

Tiny home in Ashland

4.83 out of 5 average rating, 70 reviews

Ashland tiny home with view and barrel sauna

5–12 Aug

$143 SGD per night
Guest favourite

Home in Ashland

5.0 out of 5 average rating, 19 reviews

The Aloha House - Hot Tub - Pool

12–19 Nov

$496 SGD 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