Located just blocks away from the OSF theaters downtown, Courtside Cottage is the perfect place to land on your next visit to Ashland. Park your car and live like a local in the heart of town. You’ll feel right at home with just a two-minute walk to restaurants and boutique shops. The cottage is accessible from an alley on a very quiet residential street and has been fully remodeled with a cozy but modern aesthetic.
Our prices include all fees. No hidden fees.
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This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
About the area
Ashland
Historic Railroad District, a neighbourhood in Ashland, is home to this cottage. Oregon Cabaret Theatre and Medford Carnegie Library are local landmarks, and some of the area's attractions include ScienceWorks Hands-On Museum and The RRRink. Medford Dance Arts Center and Children's Museum are also worth visiting.
Medford, OR (MFR-Rogue Valley Intl.) - 24 min drive
Restaurants
Zoey's Cafe - 4 min walk
Happy Thai Express - 4 min walk
Noble Coffee Roasting - 5 min walk
The Growler Guys - 1 min walk
Ruby's - 6 min walk
Frequently asked questions
Is Courtside Cottage - WalkScore 93 - Dog Friendly pet-friendly?
Yes, this property allows dogs (limit 3 total).
How much does it cost to stay at Courtside Cottage - WalkScore 93 - Dog Friendly?
As of 9 May 2026, prices found for a 1-night stay for 2 adults at Courtside Cottage - WalkScore 93 - Dog Friendly on 1 Aug 2026 start from £191, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Courtside Cottage - WalkScore 93 - Dog Friendly?
On-site parking is available at the property.
What time is check-in at Courtside Cottage - WalkScore 93 - Dog Friendly?
Check-in begins at 4:00 PM.
What time is check-out at Courtside Cottage - WalkScore 93 - Dog Friendly?
Checkout is at 11:00 AM.
Where is Courtside Cottage - WalkScore 93 - Dog Friendly located?
Located in Historic Railroad District, this cottage is within a 5-minute walk of Ashland Library and Oregon Cabaret Theatre. Allen Elizabethan Theatre and Angus Bowmer Theatre are also within 10 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The cottage is in a wonderful location for access to downtown Ashland. Less than a block away from a coffee shop and beer pub too! It is very clean and well-appointed.
Cottage was perfect for the 2 of us and our dog. Very clean with very comfortable king size bed. Great location within walking distance of downtown, restaurants and coffee shops. Off street parking right outside door. It was nice to have washer and dryer in unit. We will definitely be staying here in the future.
Teresa S.
Stayed 7 nights in Oct 2025
Response from VrboOwner on 24 Oct 2025
Thanks for staying at Courtside Cottage. Come back anytime.
The location was wonderful; off the street but easily walkable to everywhere we wanted to go. The EV charger was an awesome plus, saving us time when we had to get back on the road. The whole place was really well outfitted, especially the bathroom. We will definitely be back.
Lovely cottage, meticulously clean, very comfortable bed. Perfect location for walking to the OSF and many good restaurants. Not many places for our dog, but he is mainly an indoor dog, so that was okay. Definite would stay again when he is not with us.
Kris K.
Stayed 3 nights in Sep 2025
Response from VrboOwner on 21 Sept 2025
Thanks for staying! Hope to see you in the future.
Tastefully decorated, very comfortable and quiet! I truly enjoyed staying at the Courtside Cottage. Great location within walking distance to many options for great food and beverages.
For our visit to Ashland, this was a perfect home base. It's a great spot to walk from and enjoy the many nearby shops, restaurants, theater, and Lithia Park. The host really offered everything we needed: umbrellas, washer and dryer with supplies, extra towels, and even coffee. A great place to stay.
I had a wonderful stay! It was nice to have this lovely place to relax after a long drive with all the comforts of home.
Marla S.
Stayed 1 night in Dec 2024
Response from VrboOwner on 1 Jan 2025
You're welcome back anytime.
Verified
10/10 Excellent
Kim
11 Aug 2025
Liked: Cleanliness, amenities, property conditions & facilities, communication
Lovely studio cottage with high-end kitchenette, king bed, gorgeous bathroom, and thoughtful touches everywhere.
Plus, had a slight problem with the microwave and the owner called from Japan to help us solve it (CFI tripped).
I have been to Ashland before and this is really well situated but off a main street so private and quiet.
Everything about this rental is top notch! Great spot, very well appointed and the location is excellent. We stay here every year and always look forward to our next visit!
Stephanie R.
Stayed 5 nights in May 2024
About the host
Hosted by Michael Hoyt
Premier Host
They consistently provide great experiences for their guests