The Cottage @ Hillcrest Orchard

Entire cottage hosted by Terry & Barbara

  1. 2 guests
  2. 1 bedroom
  3. 1 bed
  4. 1 bath
Self check-in
Check yourself in with the keypad.
Great location
100% of recent guests gave the location a 5-star rating.
Great check-in experience
93% of recent guests gave the check-in process a 5-star rating.


Every booking includes free protection from Host cancellations, listing inaccuracies, and other issues like trouble checking in.
This historic little cottage boasts an incredible location for wine tasting and gorgeous views. Located on the grounds of the 250 acre Hillcrest Orchard Estate and RoxyAnn Winery, The Cottage will not disappoint for your next getaway!
Enjoy a complimentary wine tasting or glass of wine at the RoxyAnn Tasting Room.

This listing does not have a kitchen & has a hide-a-bed. If you need a space with a kitchen & regular bed please see The Carriage House @ Hillcrest Orchard - Airbnb room 17433760

The space
The cottage, built in 1926 and, though greatly cared for, shows its age in some places. It sits on the grounds of the historic 250 acre Hillcrest Orchard estate on the outskirts of Medford. Hillcrest Orchard has both pear and peach orchards and a vineyard. A rural feel but close to many amenities. RoxyAnn Winery is on the same property. Approximately 10 miles to the Britt Festival Pavilion and 14 miles to the Oregon Shakespeare Festival in Ashland. Crater Lake is only a 1 1/2 hour drive.
We are the perfect halfway point between Seattle and the Bay Area

Where you'll sleep

1 sofa bed

What this place offers

Free parking on premises
Air conditioning
Hair dryer
Long term stays allowed

Select check-in date

Add your travel dates for exact pricing

4.80 out of 5 stars from 104 reviews


Where you’ll be

Medford, Oregon, United States

A rural feel yet close to many amenities...
RoxyAnn Winery is on site
The Good Bean Coffee shop is across the street
Restaurants and Grocery store are a quick 1.5 mile drive
Centennial Golf Club and Rogue Valley Country club are both within a 5 minute drive
Rogue Valley Mall - 4 miles
Oregon Shakespeare Festival—12.5 miles
Britt Festival—10 miles
Craterian Theater at The Collier Center for the Performing Arts - 3 miles

Hosted by Terry & Barbara

  1. Joined in June 2016
  • 174 Reviews
  • Identity verified
We have been a part of Hillcrest Orchard for 36 years.

During your stay

Please call/message us when you arrive to let us know you arrived and also when you leave.
Please don't hesitate to call during your stay.
  • Response rate: 100%
  • Response time: within an hour
To protect your payment, never transfer money or communicate outside of the Airbnb website or app.

Things to know

House rules

Check-in: After 3:00 PM
Checkout: 1:00 PM
Self check-in with keypad
Not suitable for children and infants
No smoking
No pets
No parties or events

Health & safety

Airbnb's COVID-19 safety practices apply
Carbon monoxide alarm
Smoke alarm

Cancellation policy