Compare Ashland Guest House Rentals

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
$114 nightly
The price is $126 total per night
$126 total
Apr 15 - Apr 16
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities.
Free WiFi
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
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
$311 nightly
The price is $314 total per night
$314 total
May 4 - May 5
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities.
Pet friendly
Air conditioning
Near Downtown- Kitchen-Washer/Dryer-Parking

Near Downtown- Kitchen-Washer/Dryer-Parking

Medford OR
$240 nightly
The price is $262 total per night
$262 total
Apr 21 - Apr 22
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
Rogue River Guesthouse: Rural river views near I-5

Rogue River Guesthouse: Rural river views near I-5

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
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
$169 nightly
The price is $171 total per night
$171 total
Apr 15 - Apr 16
Total with taxes and fees
This guesthouse is a smoke-free guesthouse.
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
    $100 nightly
    The price is $112 total per night from Apr 19 to Apr 20
    $112 total
    Apr 19 - Apr 20
    Total with taxes and fees
    9.4/10 Exceptional! (1,751 reviews)
    Ashland Hills Hotel & Suites

    Ashland Hills Hotel & Suites

    2525 Ashland St Ashland OR
    $115 nightly
    The price is $128 total per night from Apr 19 to Apr 20
    $128 total
    Apr 19 - Apr 20
    Total with taxes and fees
    8.8/10 Excellent! (1,456 reviews)
    Ashland Springs Hotel

    Ashland Springs Hotel

    212 E Main St Ashland OR
    $111 nightly
    The price is $123 total per night from Apr 19 to Apr 20
    $123 total
    Apr 19 - Apr 20
    Total with taxes and fees
    9.2/10 Wonderful! (1,006 reviews)

Ashland Guest Houses essential information

Accommodation
10 Guest Houses
Lowest Price
$112
Highest Price
$314
Popular accommodation
Charleen's Cottage~Couple Perfect!Great Location! A Gem!, Spacious Cottage -Hot Tub, Patio, Fire Table, 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., Near Downtown- Kitchen-Washer/Dryer-Parking, Rogue River Guesthouse: Rural river views near I-5, 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., Carlisle Garden Suites

More to Explore