Book Guest Houses in Ashland

Start date: Check-in selected.
To Date
End date: Check-out

Wander Wisely with exceptional service, 24/7 support

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

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
The price is CA $104 per night
CA $104
CA $145 total
Dec 15 - Dec 16
includes taxes & fees
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 $136 per night
CA $136
CA $234 total
Dec 11 - Dec 12
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.
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 $193 per night
CA $193
CA $573 total
Jan 9 - Jan 10, 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
Get rates
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
Get rates
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
Rogue River Guesthouse - River and Whitewater Views!

Rogue River Guesthouse - River and Whitewater Views!

Gold Hill OR
Get rates
Stay at this guesthouse in Central Point. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Gold Hill Library and Lower Table Rock are located nearby.
Near Downtown Studio-Parking-SmartTV -Kitchenette

Near Downtown Studio-Parking-SmartTV -Kitchenette

Medford OR
Get rates
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.
Near Downtown- Kitchen-Washer/Dryer-Parking

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR
Get rates
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
Get rates
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.
Don't see what you're looking for?
See all available properties in Ashland
View all properties
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 $130 per night from Dec 14 to Dec 15
CA $130
CA $160 total
Dec 14 - Dec 15
includes taxes & fees
9.4/10 Exceptional! (1,015 reviews)

Ashland Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
CA $99
Highest Price
CA $573
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, Rogue River Guesthouse - River and Whitewater Views!, Near Downtown Studio-Parking-SmartTV -Kitchenette, Near Downtown- Kitchen-Washer/Dryer-Parking, Carlisle Garden Suites

Explore more Guest Houses

More places to stay in Ashland