
Oregon Shakespeare Festival
09/08 – 09/13
$367/nighttotal: $1835 (5 )
The Matriarch| Suite 3 | Pet Friendly
1 2apartment , Ashland
This Ashland, Oregon apartment rental is a private suite in a historic 1894 house in the Railroad District, a 6-minute walk from the Oregon Shakespeare Festival and a 5-minute walk from numerous restaurants.
This 320-square-foot studio features a king-sized bed, a separate living area with streaming services, a kitchenette, and accommodates two guests, with access to a shared patio and communal BBQ (seasonal).
This 320-square-foot studio features a king-sized bed, a separate living area with streaming services, a kitchenette, and accommodates two guests, with access to a shared patio and communal BBQ (seasonal).

Oregon Shakespeare Festival
09/08 – 09/13
$213/nighttotal: $1065 (5 )
The Ashland Social | Guest Studio
1 2studio , Ashland
This studio apartment is conveniently located just a short walk from Ashland Plaza, putting you close to the city's center and its many attractions. The studio consistently receives excellent reviews from guests, highlighting its comfortable and convenient features.
The apartment offers a spacious king-size bed, perfect for couples or solo travelers. Guests can enjoy a kitchenette with a hot plate, fridge, microwave, and other appliances, allowing them to prepare light meals and snacks. The studio also provides fast Wi-Fi, ample street parking, and a private and quiet space for relaxation.
The apartment offers a spacious king-size bed, perfect for couples or solo travelers. Guests can enjoy a kitchenette with a hot plate, fridge, microwave, and other appliances, allowing them to prepare light meals and snacks. The studio also provides fast Wi-Fi, ample street parking, and a private and quiet space for relaxation.

Oregon Shakespeare Festival
10/13 – 10/20
$374/nighttotal: $2618 (7 )
2br Ashland Retreat: Steps To Shakespeare
2 3apartment , Ashland
This Ashland vacation rental is ideally located in the Historic Railroad District, a 5-minute walk from the Oregon Cabaret Theatre, Allen Elizabethan Theatre, and Angus Bowmer Theatre, as well as the Thomas Theatre and Oregon Shakespeare Festival.
This 1600-square-foot house features two bedrooms, three bathrooms, accommodates four guests, and includes a fully equipped kitchen, a relaxing balcony, and a private garden with barbecue grills.
This 1600-square-foot house features two bedrooms, three bathrooms, accommodates four guests, and includes a fully equipped kitchen, a relaxing balcony, and a private garden with barbecue grills.

Oregon Shakespeare Festival
09/13 – 09/25
$194/nighttotal: $2328 (12 )
Chateau Herbe ~ Rosalind Carriage House 1bdr Apt
1 2apartment , Ashland
This Ashland carriage house apartment is located in a gated castle community near I-5 and downtown Ashland, offering easy access to both.
The one-bedroom, one-bathroom unit sleeps four guests and features a kitchen, air conditioning, a jacuzzi, a sauna, parking, and access to the chateau's sunroom, library, coffee bar, patio, vineyards, gardens, orchards, pond, and fountain.
The one-bedroom, one-bathroom unit sleeps four guests and features a kitchen, air conditioning, a jacuzzi, a sauna, parking, and access to the chateau's sunroom, library, coffee bar, patio, vineyards, gardens, orchards, pond, and fountain.

Oregon Shakespeare Festival
09/08 – 09/13
$465/nighttotal: $2325 (5 )
Whimsy On B | 2br Steps To Downtown
2 2apartment , Ashland
This apartment offers prime placement in Ashland, situated mere steps from the Ashland Food Co-op and a short walk to downtown's theaters, shops, and cafes.
This rental accommodates up to 4 guests with two bedrooms, a living room with a TV, a full kitchen, and an outdoor space with a porch swing, all within a quiet triplex with shared parking and courtyard.
This rental accommodates up to 4 guests with two bedrooms, a living room with a TV, a full kitchen, and an outdoor space with a porch swing, all within a quiet triplex with shared parking and courtyard.

Oregon Shakespeare Festival
09/08 – 09/13
$149/nighttotal: $745 (5 )
Florence Room At Chateau Herbe
1 2castle , Ashland
Château Herbe, near I-5 and downtown Ashland, Oregon, offers stunning mountain and garden views and is minutes from Grizzly Peak and Weisinger Family wineries.
This one-bedroom, one-bathroom castle lodging boasts a queen-sized bed, private en-suite bath, access to a communal sunroom, library, and patio, and accommodates two guests; explore the on-site vineyard, gardens, and orchards.
This one-bedroom, one-bathroom castle lodging boasts a queen-sized bed, private en-suite bath, access to a communal sunroom, library, and patio, and accommodates two guests; explore the on-site vineyard, gardens, and orchards.

Oregon Shakespeare Festival
09/13 – 09/25
$149/nighttotal: $1788 (12 )
Ashland Tiny Home With View And Barrel Sauna
1 2cabin , Ashland
This Ashland, Oregon craftsman tiny home, located five minutes from downtown and west of Emigrant Lake, offers a secluded retreat on a three-acre property.
The 170-square-foot (8.5 ft x 20 ft) space includes a queen-sized bed in an upstairs loft, one bedroom, one bathroom, a full kitchen with modern appliances, a private deck with BBQ, a shared barrel sauna, and accommodates two guests.
The 170-square-foot (8.5 ft x 20 ft) space includes a queen-sized bed in an upstairs loft, one bedroom, one bathroom, a full kitchen with modern appliances, a private deck with BBQ, a shared barrel sauna, and accommodates two guests.

Oregon Shakespeare Festival
06/25 – 06/27
$375/nighttotal: $750 (2 )
Incredible 3 Bdrm On 5 Acres With Sauna And Creek
3 2apartment , Ashland
This three-bedroom Ashland apartment rental is situated in the Ashland farmlands, 1.5 miles from Emigrant Lake and a 12-minute drive from downtown Ashland.
The 3-bedroom, 2-bathroom home boasts a chef's kitchen, wood-fired sauna, event tent, trampoline, zip line, treehouse, and accommodates up to four guests, offering unique amenities alongside its proximity to Ashland's attractions.
The 3-bedroom, 2-bathroom home boasts a chef's kitchen, wood-fired sauna, event tent, trampoline, zip line, treehouse, and accommodates up to four guests, offering unique amenities alongside its proximity to Ashland's attractions.

Oregon Shakespeare Festival
09/13 – 09/25
$257/nighttotal: $3084 (12 )
Modern Airy Retreat - Views, Walk To Everything
1 2house , Ashland
This Ashland Railroad District studio apartment is a five-minute walk from downtown, ten minutes from Lithia Park and the Oregon Shakespeare Festival.
The modern unit, sleeping two, features a well-equipped kitchenette with coffee supplies and dedicated off-street parking—a rare find in downtown Ashland—and offers proximity to Noble Coffee Roasters, Peerless Restaurant, and the Bear Creek Bike Trail.
The modern unit, sleeping two, features a well-equipped kitchenette with coffee supplies and dedicated off-street parking—a rare find in downtown Ashland—and offers proximity to Noble Coffee Roasters, Peerless Restaurant, and the Bear Creek Bike Trail.








