Compare Ashland Guest House Rentals

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

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

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
$101 nightly
The price is $112 total per night
$112 total
Jan 10 - Jan 11
Total with taxes and fees
Guests of this guesthouse enjoy features like a water park and laundry facilities.
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
$166 nightly
The price is $169 total per night
$169 total
Jan 12 - Jan 13
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
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
$425 nightly
The price is $428 total per night
$428 total
Jan 8 - Jan 9
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities.
Pet friendly
Air conditioning
Spacious Cottage -Hot Tub, Patio, Fire Table, WIFI

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

Central Point OR
Guests staying at this guesthouse enjoy a hot tub and laundry facilities.
Hot Tub
Free WiFi
Near Downtown- Kitchen-Washer/Dryer-Parking

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR
$142 nightly
The price is $155 total per night
$155 total
Jan 20 - Jan 21
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities and local meal delivery service.
Kitchen
Washer
Rogue River Guesthouse - River and Whitewater Views!

Rogue River Guesthouse - River and Whitewater Views!

Gold Hill OR
At this guesthouse, guests have access to features like laundry facilities. RV, bus, and truck parking is available. This smoke-free guesthouse also has barbecue grills.
Pet friendly
Free WiFi
Near Downtown Studio-Parking-SmartTV -Kitchenette

Near Downtown Studio-Parking-SmartTV -Kitchenette

Medford OR
$129 nightly
The price is $141 total per night
$141 total
Jan 11 - Jan 12
Total with taxes and fees
At this apartment, guests have access to features like local meal delivery service.
Kitchen
Free WiFi
Near Downtown- Kitchen-Washer/Dryer-Parking

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR
$244 nightly
The price is $266 total per night
$266 total
Jan 8 - Jan 9
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities and local meal delivery service.
Pet friendly
Free WiFi
Carlisle Garden Suites

Carlisle Garden Suites

3 out of 5
637 E Main St Ashland OR
Guests staying at Carlisle Garden Suites enjoy free WiFi in public areas, a terrace, and a garden. If you plan to drive, free parking is available. The front desk is staffed 24/7 to help with tours or tickets, and answer any questions about the accommodations. This smoke-free guesthouse also has a picnic area.
Parking included
Free WiFi
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.

Hotel Options in Ashland

    Stratford Inn

    Stratford Inn

    555 Siskiyou Blvd Ashland OR
    $86 nightly
    The price is $96 total per night from Jan 8 to Jan 9
    $96 total
    Jan 8 - Jan 9
    Total with taxes and fees
    9.2/10 Wonderful! (1,619 reviews)
    Ashland Hills Hotel & Suites

    Ashland Hills Hotel & Suites

    2525 Ashland St Ashland OR
    $109 nightly
    The price is $122 total per night from Jan 11 to Jan 12
    $122 total
    Jan 11 - Jan 12
    Total with taxes and fees
    8.8/10 Excellent! (1,477 reviews)
    Ashland Springs Hotel

    Ashland Springs Hotel

    212 E Main St Ashland OR
    $91 nightly
    The price is $101 total per night from Jan 14 to Jan 15
    $101 total
    Jan 14 - Jan 15
    Total with taxes and fees
    9.2/10 Wonderful! (1,004 reviews)

Ashland Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
$96
Highest Price
$428
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

More to Explore