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Courtside Cottage - WalkScore 93 - Dog Friendly

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A modern living room with a grey sofa, a small table, and a basket on a white ottoman.
A modern bedroom with a large bed, a grey sofa, and a dining area.
A modern living room with a fireplace, a sofa, a coffee table, and a red accent wall.
A wooden table with metal chairs, a potted plant, and a metal lantern in a patio area.
A modern kitchen with a stainless steel coffee maker, a kettle, and a sink.

Reviews

10 out of 10
Exceptional
Accommodating 4 guests, this cottage features 1 bedroom and 1 bathroom. It includes a patio for outdoor enjoyment and welcomes pets. Explore the Ashland Library and Oregon Cabaret Theatre during your visit.

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Near Oregon Shakespeare Festival
1 bedroom1 bathroomSleeps 4

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchenette
  • Laundry room
  • Air-conditioning
  • Deck or patio

Explore the area

View in a map
Ashland, OR
  • Place, Oregon Cabaret Theatre
    ‪3 min walk‬
  • Place, Lithia Park
    ‪6 min walk‬
  • Place, Oregon Shakespeare Festival
    ‪6 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪23 min drive‬

Where you'll sleep

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

Courtside Cottage was named one of the Top Ten Traveler's Accommodations in Ashland by The Oregonian. Located just blocks away from the OSF theaters downtown, it is the perfect place to land on your next visit to Ashland, park your car and live like a local. You’ll feel right at home minutes from Ashland's main attractions. Please read all of the house rules and particulars regarding parking. Thanks!

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Property grounds
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10.0 out of 10, Exceptional, (238 reviews)
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House Rules

Check in after 4:00 PM
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

Property # 3202969vb
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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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.
View more Cottages in AshlandOpens in a new window
Map
Ashland, OR

What's nearby

  • Ashland Library - 2 min walk - 0.2 km
  • Oregon Cabaret Theatre - 3 min walk - 0.3 km
  • Lithia Park - 6 min walk - 0.6 km
  • Oregon Shakespeare Festival - 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

  • ‪Martolli's Hand Tossed Pizza - ‬7 min walk
  • ‪Case Coffee Roasters - ‬7 min walk
  • ‪Ruby's - ‬6 min walk
  • ‪RedZone Sports Bar N' Grill - ‬2 min walk
  • ‪The Growler Guys - ‬2 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 1 Oct, 2026, prices found for a 1-night stay for 2 adults at Courtside Cottage - WalkScore 93 - Dog Friendly on 23 Feb, 2027 start from S$516, 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 73 out of 74 reviews
Rating 8 - Good. 1 out of 74 reviews
Rating 6 - Okay. 0 out of 74 reviews
Rating 4 - Poor. 0 out of 74 reviews
Rating 2 - Terrible. 0 out of 74 reviews

10/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This cottage was very clean and beautifully decorated. It was located in a lovely area that was close to good food and the theater! We loved our time there and highly recommend this place to others.
Stayed 5 nights in Sep 2026
Response from VrboOwner on 27 Sept, 2026
Thanks for staying with us! Comeback anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great communicationGreat location to walking to townVery clean and comfortableHighly recommend
Stayed 3 nights in Sep 2026
Response from VrboOwner on 18 Sept, 2026
Thanks for the kind words. Glad you were able to stay with up!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great cottage in an awesome location!
Stayed 3 nights in Jul 2026
Response from VrboOwner on 2 Aug, 2026
Thanks for choosing Courtside Cottage!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Extremely clean and comfortable. Host let us in early when he didn’t have to. Thanks for the great place!
Stayed 1 night in Aug 2026
Response from VrboOwner on 26 Aug, 2026
Thanks for staying with us!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very easy and convenient stay. Walking distance to park and downtown. Cute studio.
Stayed 2 nights in Jul 2026
Response from VrboOwner on 31 Jul, 2026
Glad you enjoyed your visit. Comeback anytime.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent stay. Very responsive host. Would come back
Stayed 1 night in Jul 2026
Response from VrboOwner on 14 Jul, 2026
Thanks for choosing Courtside. Comeback anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place was beautiful and just as described the cute little kitchen was perfect for our stay and it could not be a better location. Michael is a great communicator and friendly and very helpful.
Stayed 4 nights in Jul 2026
Response from VrboOwner on 28 Jul, 2026
Glad you enjoyed your stay. Comeback anytime.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location in the heart of downtown
Stayed 3 nights in May 2026
Response from VrboOwner on 4 Jun, 2026
Thanks for staying with us!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Spacious, clean studio to explore Ashland!
Stayed 1 night in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, comfortable and great location. We really enjoyed our stay and look forward to returning.
Stayed 2 nights in Feb 2026
Response from VrboOwner on 21 Feb, 2026
Thanks for staying with us.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was my first vrbo stay and it was arranged on short notice. The owner was very patient with my unfamiliarity with the process and multiple questions. The unit is very cleverly constructed with everything needed and in a fantastic location near downtown. Very accommodating for our dogs. My only regret is that we didn't have time to enjoy a glass of wine on the charming little patio. I hope to return.
Stayed 2 nights in Jul 2026
Response from VrboOwner on 22 Jul, 2026
Glad it all worked out well. Comeback anytime.
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Courtside cottage is the perfect little place in the perfect location.
Stayed 6 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place to stay very quaint very clean. Host is very gracious and communicated perfectly before the trip. Definitely would stay here again.
Stayed 1 night in Nov 2025
Response from VrboOwner on 26 Nov, 2025
Thanks for choosing Courtside Cottage!
Verified review

10/10 Excellent

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

Great place to stay!

A clean cozy cottage perfectly located to enjoy Ashland.
Stayed 6 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location and beautiful space. Easy walk to downtown.
Stayed 1 night in Oct 2025
Response from VrboOwner on 22 Oct, 2025
Thanks for staying with us!
Verified review

10/10 Excellent

Liked: Cleanliness, amenities, property conditions & facilities, communication
Very clean, great location. Well appointed . Loved it and would definitely come back.
Stayed 1 night in Dec 2025
Verified review

10/10 Excellent

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

Great location

Great location and very cute place.
Stayed 2 nights in Dec 2024
Response from VrboOwner on 5 Jan, 2025
Thanks for staying!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Location and Comfortable Unit.
Stayed 2 nights in Aug 2025
Response from VrboOwner on 10 Aug, 2025
Thanks for staying!
Verified review

10/10 Excellent

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
Response from VrboOwner on 27 Jul, 2025
Thanks for staying with us. Hope to see you in the future!
Verified review

10/10 Excellent

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
Response from VrboOwner on 10 Oct, 2025
Thank so much for staying with us.
Verified review

10/10 Excellent

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
Response from VrboOwner on 6 Oct, 2025
Come back anytime!
Verified review

10/10 Excellent

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

Great place!

Excellent condition with everything we needed. Would definitely stay again.
Stayed 1 night in Jul 2023
Verified review

10/10 Excellent

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

Great place in awesome location

Clean and perfect stay for two. Friendly owners.
Stayed 5 nights in Jun 2024
Verified review

10/10 Excellent

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
Response from VrboOwner on 26 Jul, 2025
Glad your stay went well. Thanks for choosing Courtside!

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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