Ashland Vacation Rentals

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Vacation Rentals in Ashland

Jacksonville Place

Medford OR

$169 nightly

$190 total

Dec 7 - Dec 8

Total with taxes and fees

A stay at this vacation home places you in the heart of Medford, within a 5-minute drive of Blackbird Statue and Stewart Meadows Golf Course.

Kitchen

Washer

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Ashland OR

$452 nightly

$504 total

Dec 6 - Dec 7

Total with taxes and fees

Located in Ashland, this vacation home is within a 15-minute walk of Ashland Creek and Lithia Park.

Hot Tub

Kitchen

New house with king beds and 3 full bathrooms

Medford OR

$252 nightly

$284 total

Dec 6 - Dec 7

Total with taxes and fees

A stay at this vacation home places you in the heart of Medford, within a 5-minute drive of Medford Railroad Park and Rogue Karting.

Kitchen

Washer

New Downtown 3 Bedroom Upstairs Flat with views

Ashland OR

A stay at this vacation home places you in the heart of Ashland, steps from Ashland Library and 6 minutes by foot from Oregon Cabaret Theatre.

Kitchen

Washer

East Main Downtown Bungalow

Ashland OR

With a stay at this vacation home in Ashland (Historic Railroad District), you'll be steps from Ashland Library and 6 minutes by foot from Oregon Cabaret Theatre.

Kitchen

Washer

Award Winning Britt Bungalow in the Historical Heart of Jacksonville Oregon

Jacksonville OR

$254 nightly

$281 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Jacksonville (Jacksonville Historic District), you'll be within a 5-minute walk of Sarah Zigler Interpretive Trail and Jacksonville Cemetery.

Kitchen

Washer

1907 Charmer, Perfect Downtown Location, So Clean!

Ashland OR

A stay at this vacation home places you in the heart of Ashland, steps from Ashland Library and Oregon Cabaret Theatre.

Kitchen

Washer

Premier Downstairs Flat in Perfect Down Town Location

Ashland OR

A stay at this vacation home places you in the heart of Ashland, steps from Ashland Library and 6 minutes by foot from Oregon Cabaret Theatre.

Kitchen

Washer

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Ashland OR

A stay at this vacation home places you in the heart of Ashland, within a 10-minute walk of Ashland Library and Allen Elizabethan Theatre.

Kitchen

Washer

The Rellik House and Winery

968 Old Stage Rd Central Point OR

$276 nightly

$279 total

Jan 2 - Jan 3, 2026

Total with taxes and fees

With a stay at The Rellik House and Winery in Central Point, you'll be steps from Caprice Vineyards and a 3-minute drive from Kharmic Creations.

Pool

Hot Tub

Whether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!

Central Point OR

$289 nightly

$294 total

Dec 12 - Dec 13

Total with taxes and fees

With a stay at this vacation home in Central Point, you'll be within a 10-minute walk of Rogue Creamery and Central Point Library.

Kitchen

Washer

Jacksonville Creekside Inn

Jacksonville OR

With a stay at this vacation home in Jacksonville (Jacksonville Historic District), you'll be within a 5-minute walk of Kharmic Creations and Art Presence Art Center.

Hot Tub

Kitchen

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.