Entire guesthouse in Ashland, Oregon

4 guests
1 bedroom
2 beds
1 bath

Rated 4.67 out of 5 stars.9 reviews

Hosted by Haley

Superhost
2 years hosting

Listing highlights

Exceptional check-in experience

Recent guests gave the check-in process a 5-star rating.

Self check-in

Check yourself in with the keypad.

Haley is a Superhost

Superhosts are experienced, highly rated Hosts.

Sunset Cottage at Grizzly Peak Winery is a light and airy studio with high ceilings, natural light, wood burning fireplace, full kitchen with all the amenities you could hope for, a comfy couch with smart tv, and a spacious dining area. With room for 4, this cottage is a great place for families and friends to spend time relaxing and enjoying the beautiful views and grounds at the winery. Guests are always welcome to a complimentary evening of music and a food truck meal during concert season.

The space
Discover Ashland, Oregon — Where Outdoor Adventure Meets Culinary Art

Escape to Ashland, Oregon, a vibrant mountain town where breathtaking outdoor adventures pair perfectly with an inspired food scene. Our vacation rentals place you minutes from world-class hiking, scenic trails, and river adventures—whether you’re exploring Lithia Park, hiking the Siskiyou Mountains, or enjoying a peaceful morning stroll downtown.

After a day outdoors, indulge in Ashland’s celebrated culinary culture. From farm-to-table restaurants and award-winning wineries to artisan coffee shops and local bakeries, Ashland is a haven for food lovers. Fresh, local ingredients and creative chefs turn every meal into an experience.
Our thoughtfully curated vacation rentals offer comfort, style, and the perfect home base for your Ashland getaway—ideal for outdoor enthusiasts, foodies, and anyone craving a refreshing blend of nature and culture.

Come hike, taste, relax, and repeat in Ashland.