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Ashland vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Ashland

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

Superhost
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
$176 per night
Superhost
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.
$145 per night
Superhost
Private room in Ashland
Mexico Airbnb at Wood Hamlet, by Downtown
The Wood Hamlet Mexico unit has its own bathroom and entrance. It is a short walk to town for the restaurants, shopping, galleries and the lovely 72-acre Lithia Park. Mexico unit has a warm Latin flavor. It is in carriage house and up about 7 steps. Queen bed with full bath. Sitting area. Mini frig, coffee, tea & microwave. Wi-fi. Beautiful, garden with sitting areas & swimming pond. Private parking. (Ashland City Permit# 17-080) NO SMOKING ON PREMISES
$71 per night

Stay near Ashland's top sights

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

Ashland house rentals

Superhost
Private room in Ashland
Peaceful & Private Bedroom with Kitchenette!
$72 per night
Superhost
Private room in Ashland
Ashland Dawn Room, Walk to town!
$75 per night
Home in Ashland
Cowslip's quiet, central, Cuckoo-Bud Suite
$119 per night
Superhost
Home in Ashland
Casa Bella Bungalow
$95 per night
Superhost
Home in Ashland
Harmony Cottage - 2bd/1ba, 10 min from downtown!
$108 per night
Home in Ashland
Cowslip's Rosebud Garden Suite, peaceful, central
$155 per night
Superhost
Home in Ashland
The Barn at Emigrant Creek
$151 per night
Superhost
Home in Ashland
Helman Street Penthouse with a View
$200 per night
Superhost
Private room in Ashland
The Carter House in Historic Downtown Ashland
$129 per night
Superhost
Private room in Ashland
$125 a night! LARGE flat one block to town!
$125 per night
Superhost
Home in Ashland
Helman House
$168 per night
Superhost
Home in Ashland
Coyote Moon
$200 per night
  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland