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Courtside Cottage - WalkScore 93 - Dog Friendly

Cottage in Ashland with kitchenette and patio

Photo gallery for Courtside Cottage - WalkScore 93 - Dog Friendly

Room
Living area
Living area
Room
Private kitchen

Reviews

10 out of 10
Exceptional
1 bedroom1 bathroomSleeps 4

Popular amenities

  • Dryer
  • Kitchen
  • Air conditioning

Explore the area

View map
Ashland, OR
  • Place, Oregon Shakespeare Festival
    ‪6 min walk‬
  • Place, Lithia Park
    ‪6 min walk‬
  • Place, Southern Oregon University
    ‪15 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪22 min drive‬

Rooms & beds

1 bedroom (sleeps 4)

Studio

1 King Bed and 1 Double Sofa Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchenette
Dining area

About this property

Courtside Cottage - WalkScore 93 - Dog Friendly

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.

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Amenities

Kitchen
Dryer
Pet-friendly
Free WiFi
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 3 total)
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Smoking

Smoking is not permitted
Cannabis packaging is strictly forbidden.

Important information

You need to know

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.
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Map
Ashland, OR

What's nearby

  • Oregon Cabaret Theatre - 3 min walk - 0.3 km
  • Allen Elizabethan Theatre - 6 min walk - 0.6 km
  • Oregon Shakespeare Festival - 6 min walk - 0.6 km
  • Lithia Park - 6 min walk - 0.6 km
  • Southern Oregon University - 15 min walk - 1.3 km

Getting around

  • Medford, OR (MFR-Rogue Valley Intl.) - 24 min drive

Restaurants

  • ‪Noble Coffee Roasting - ‬5 min walk
  • ‪The Growler Guys - ‬1 min walk
  • ‪Ruby's - ‬6 min walk
  • ‪Zoey's Cafe - ‬4 min walk
  • ‪RedZone Sports Bar N' Grill - ‬2 min walk

Frequently asked questions

Is Courtside Cottage - WalkScore 93 - Dog Friendly pet-friendly?

Yes, this property allows dogs (limit 3 total).

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

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Eco-friendliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy
Rating 10 - Excellent. 57 out of 58 reviews
Rating 8 - Good. 1 out of 58 reviews
Rating 6 - Okay. 0 out of 58 reviews
Rating 4 - Poor. 0 out of 58 reviews
Rating 2 - Terrible. 0 out of 58 reviews

Reviews

10/10 Excellent

Cari D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and beautiful space. Easy walk to downtown.
Stayed 1 night in Oct 2025

10/10 Excellent

Joey M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 1 night in Oct 2025

10/10 Excellent

Jolanta G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean, well designed studio with a walking distance to downtown Ashland. Lovely host. Would stay again.
Stayed 2 nights in Oct 2025

10/10 Excellent

Teresa S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 7 nights in Oct 2025

10/10 Excellent

John V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location and Comfortable Unit.
Stayed 2 nights in Aug 2025

10/10 Excellent

Kim C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place is exactly as pictured and extremely comfortable. It is such a great neighborhood with easy walks to restaurants and plays.
Stayed 2 nights in Jul 2025

10/10 Excellent

Kris K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Sep 2025

10/10 Excellent

Lindsay M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

A perfect jumping off spot for Ashland. Easy all around, very nice and clean. We were very pleased.
Stayed 2 nights in Jul 2025

10/10 Excellent

Nichole A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay!

The place was perfect for my husband and I traveling with our pup. Many restaurants and activities are within walking distance of the cottage - we would stay here again next time we're in Ashland.
Stayed 3 nights in Sep 2024

10/10 Excellent

Keith A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean, conveniently located, lovely cottage in Ashland

Michael’s cottage was as described with every amenity we could need in our two night stay in Ashland. Check in and check out were easy and there was a comprehensive list of recommended restaurants that were helpful. Very clean, well appointed space with a private outdoor area to enjoy as well.
Stayed 2 nights in Aug 2024

10/10 Excellent

Timothy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

OSF extravaganza

We came in for 5 days and 4 nights, staying again at the "Courtside Cottage" where we'd stayed last year. We saw 4 OSF plays, ate well, took some walks, managed our little dog, and kept our EV charged at the cottage. It all went very well. Can't think of anything that would've made it better.
Stayed 4 nights in Mar 2025

10/10 Excellent

Sue K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location

This is second time we have stayed at this property. Clean, modern and located within walking distance to OSF, restaurants, shopping and coffee houses.
Stayed 3 nights in Oct 2023

10/10 Excellent

Becky S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ideal location

Thoroughly enjoyed our stay in this modern cottage, perfectly located for walking to the triangle, restaurants, theaters and parks. We hope to return soon!
Stayed 7 nights in May 2023

10/10 Excellent

Jake B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Home

This cottage is exactly what a short term rental is supposed to be. Tasteful design, high quality materials, a comfortable bed, fantastic location close to everything, and excellent appointments and communication from the owner. My favorite place to stay in Ashland.
Stayed 2 nights in Mar 2023

10/10 Excellent

Christine L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great getaway

We had just a short overnight stopover on a road trip. The cottage was clean, comfortable and quiet and Ashland was very cute. Michael was friendly and easy to communicate with.
Stayed 1 night in Dec 2023

10/10 Excellent

Kathryn

Liked: Cleanliness, amenities, property conditions & facilities, communication
It had everything we wanted or needed for comfort, and we were able to have our dog travel and stay with us. Communication with the host was great. Many things within walking distance, including the Shakespeare festival events. We plan to return in the future and hopefully stay at this property again.
Stayed 2 nights in May 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

A cozy comfortable place

What a wonderful place to stay. We were on the go everyday, out and about, enjoying hikes, wine tasting, theater, local eateries, and local bars... one thing we always looked forward to after a busy day is that special place where we just relax in the comfort of a cozy home. It's got it all... location and amenities. It's certainly a great place to stay.
Stayed 4 nights in Jul 2023

10/10 Excellent

Deanna J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection

This rental is great. Excellent location; the owner has thought of everything; beautiful design touches; close to everything - all walkable; safe, off street parking, etc. Will definitely stay here again.
Stayed 3 nights in Jul 2023

10/10 Excellent

Gloria B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy and the best location

This was our second visit to the Courtside Cottage and we would come back any time. There is no better location in Ashland - we walked to everything and never moved our car in 4 days. We walked to the Shakespeare Festival, restaurants, coffee shops, Main Street and Lithia Park. The host Michael gives detailed and timely information. The cottage is cozy but is a master-class in efficient use of space. It has everything you need including a quaint and private front patio. It is very pet friendly and our senior dog loved her stay too.
Stayed 3 nights in Jul 2024

10/10 Excellent

Stephen G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place is actually even nicer than the photo shows, in that the couch is somewhat hidden in the photo behind the long, high table, the bathroom is very pleasant and functional and the location is quite quiet. Our dog loved it as well, in terms of settling in very comfortably.Mike was a superb host in terms of answering questions and otherwise communicating. Plus by chance we met him upon arrival, and he's a great guy in person. Wifi, AC, hot water, etc. all worked great. Comfotable bed with plentiful, easily accessible table-top power outlets on both sides. Mike provides a great looseleaf book in the cottage; it contains all sorts of valuable information and recommendations - about restaurants, stores to get basics if you need them, other places worth knowing about that are within walking and easy driving distance, etc. - as well as information about the cottage itself.The location is very fine: In a pleasant neighborhood, just off the beaten path, about a 10-minute walk or less from many shops and restaurants, as well as the Shakespeare festival. And barely five minutes from a fantastic restaurant, Cocorico (which Mike recommended), which has wonderful ambiance (including being pretty quiet), service and above all food.In sum, very highly recommended. We won't hesitate to go back, and will most likely do so during our next trip to/through Ashland.
Stayed 1 night in Aug 2025

10/10 Excellent

mike t.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect getaway

I had a chance to stay at the “Courtside” cottage for 2 weeks. Everything was well appointed, the bedding was of top quality sheets and pillows and the kitchen was very efficient. Many great touches and thought was taken to all the details and information about the cottage as well as things to do in town. It’s in a very private location and the entrance and parking was off the main street but was very walkable to the shops and restaurants. Communication with Michael, the owner, was very good. I highly recommend staying at the “courtside”.!
Stayed 15 nights in Apr 2024

10/10 Excellent

Aaron B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay. Loved the location and the host was super great.
Stayed 3 nights in Sep 2025

10/10 Excellent

Rebecca B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 2 nights in Aug 2025

10/10 Excellent

Dianne P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection!

Great location within walking distance to everything we wanted to do. Spotlessly clean, well equipped, comfortable bed…couldn’t ask for anything more!
Stayed 2 nights in Jun 2025

10/10 Excellent

Justin K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Convenient location with thoughtful amenities

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.
Stayed 5 nights in May 2025

About the host

Hosted by Michael Hoyt

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Premier Host

They consistently provide great experiences for their guests
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