Book Guest Houses in Ashland

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Featured Guest Houses in Ashland

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

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

Jacksonville OR
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Book a stay at this golf guesthouse in Jacksonville. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions Art Presence Art Center and Quady North are located nearby.
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.

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
The price is CA $135 per night
CA $135
CA $231 total
Dec 30 - Dec 31
includes taxes & fees
Stay at this guesthouse in Central Point. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Central Point Library and Rogue Creamery are located nearby.
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.

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
The price is CA $208 per night
CA $208
CA $586 total
Jan 1 - Jan 2, 2026
includes taxes & fees
Stay at this guesthouse in Central Point. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Caprice Vineyards and Jacksonville Cemetery are located nearby.
Pet-friendly
Air conditioning
Spacious Cottage -Hot Tub, Patio, Fire Table, WIFI

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

Central Point OR
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Stay at this guesthouse in Central Point. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Bi-Mart Amphitheater and The Expo are located nearby.
Hot tub
Free WiFi
Near Downtown- Kitchen-Washer/Dryer-Parking

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR
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Stay at this guesthouse in Medford. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Rogue Valley Growers and Crafters Market and Cinemark Tinseltown Medford 15 are located nearby.
Kitchen
Washer
Near Downtown Studio-Parking-SmartTV -Kitchenette

Near Downtown Studio-Parking-SmartTV -Kitchenette

Medford OR
The price is CA $98 per night
CA $98
CA $192 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Stay at this guesthouse in Medford. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Rogue Valley Growers and Crafters Market and Cinemark Tinseltown Medford 15 are located nearby.
Kitchen
Free WiFi
Near Downtown- Kitchen-Washer/Dryer-Parking

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR
The price is CA $173 per night
CA $173
CA $353 total
Jan 28 - Jan 29, 2026
includes taxes & fees
Stay at this guesthouse in Medford. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Rogue Valley Growers and Crafters Market and Cinemark Tinseltown Medford 15 are located nearby.
Pet-friendly
Free WiFi
Carlisle Garden Suites

Carlisle Garden Suites

3 out of 5
637 E Main St Ashland OR
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Stay at this guesthouse in Ashland. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Ashland Library and Oregon Cabaret Theatre are located nearby.
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.

Top trending hotels in Ashland

Lithia Springs Resort

Lithia Springs Resort

2165 W Jackson Rd Ashland OR
The price is CA $119 per night from Jan 7 to Jan 8
CA $119
CA $148 total
Jan 7 - Jan 8, 2026
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)

Ashland Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
CA $100
Highest Price
CA $586
Popular accommodation
Charleen's Cottage~Couple Perfect!Great Location! A Gem!, 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., 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., Spacious Cottage -Hot Tub, Patio, Fire Table, WIFI, Near Downtown- Kitchen-Washer/Dryer-Parking, Near Downtown Studio-Parking-SmartTV -Kitchenette, Near Downtown- Kitchen-Washer/Dryer-Parking, Carlisle Garden Suites

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