Ashland Guest Houses

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Guest Houses in Ashland

Charleen's Cottage~Couple Perfect!Great Location! A Gem!

Jacksonville OR

$95 nightly

$105 total

Dec 8 - Dec 9

Total with taxes and fees

A stay at this guesthouse places you in the heart of Jacksonville, within a 10-minute walk of Art Presence Art Center and Quady North.

Free WiFi

Air conditioning

Modern 1 BR Guest House in Central Point, OR. Your ideal Southern Oregon stopover! Features AC, full kitchen, W/D, and dedicated workspace. Quick and convenient access to I-5 and local attractions.

Central Point OR

$166 nightly

$169 total

Dec 11 - Dec 12

Total with taxes and fees

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

Pet friendly

Free WiFi

Charming Wine Country Carriage House – 2BR/2BA near Jacksonville Peaceful retreat in the heart of Southern Oregon wine country. Private, comfy, and perfect for couples or friends. Close to wineries, trails & historic Jacksonville.

Central Point OR

$400 nightly

$402 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

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

Pet friendly

Air conditioning

Spacious Cottage -Hot Tub, Patio, Fire Table, WIFI

Central Point OR

Located in Central Point, this guesthouse is a 5-minute drive from TouVelle State Recreation Site and 6 minutes from Crater Rock Museum.

Hot Tub

Free WiFi

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR

$142 nightly

$155 total

Dec 8 - Dec 9

Total with taxes and fees

A stay at this apartment places you in the heart of Medford, within a 5-minute drive of Vogel Plaza and Rogue Valley Growers and Crafters Market.

Kitchen

Washer

Rogue River Guesthouse - River and Whitewater Views!

Gold Hill OR

Located in Central Point, this guesthouse is in a rural location, a 1-minute drive from Rogue River and 7 minutes from Gold Hill Dog Park.

Pet friendly

Free WiFi

Near Downtown Studio-Parking-SmartTV -Kitchenette

Medford OR

$125 nightly

$137 total

Dec 8 - Dec 9

Total with taxes and fees

Located in Medford, this apartment is within a 15-minute walk of Bear Creek Park and Southern Oregon University Medford Campus.

Kitchen

Free WiFi

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR

$246 nightly

$269 total

Dec 8 - Dec 9

Total with taxes and fees

A stay at this guesthouse places you in the heart of Medford, within a 5-minute drive of Vogel Plaza and Rogue Valley Growers and Crafters Market.

Pet friendly

Free WiFi

Carlisle Garden Suites

637 E Main St Ashland OR

With a stay at Carlisle Garden Suites in Ashland (Historic Railroad District), you'll be a 4-minute walk from Ashland Library and 7 minutes by foot from Oregon Cabaret Theatre.

Parking included

Free WiFi

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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.