Apartment in Ashland, OR
6 guests · 2 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this apartment rental
Within walking distance, enjoy world-class Shakespeare theater, restaurants, wineries, shopping, unique coffee shops, and endless outdoor adventure with a stunning scenic backdrop! You'll be above all the fun in a hip, colorful 2 bedroom loft. Art, culture, and downtown vibes - The Urban Gypsy Loft in Southern Oregon checks all the boxes for the best weekend getaway, girl's trip or stay-cation. If outdoor adventure is your jam, you chose the right town!
This apartment is located upstairs in a 3-unit historic building on Main Street. The spacious apartment features the following;
Guest access is given within a few hours of check-in. You'll be given a unique code that allows you access into the building, and a separate code to get into the loft. Safety is a high priority for our guests :)
Other things to note; there is a breakfast spot directly below our loft, a yummy Italian restaurant, and a sexy wine bar open until 11 pm, so you can literally walk out the door and be at any of these places within seconds!
Amenities at The Urban Gypsy Loft
Family friendly
Map of Ashland, OR
Ratings and reviews
10.0 / 10.0Outstanding·Jul 2025
Property is well placed for walking to the theater's, restaurants and core town downtown shops.
8.0 / 10.0Excellent·Jun 2025
Not the best for seniors- 26 steep steps and no grab bars or mat for the shower. That being said it was comfortable and beautiful.
10.0 / 10.0Outstanding·Jun 2025
We had difficulty checking in but our host was easily accessible for us to gain entry. We appreciated the short walk to the theaters and not hassling with parking. Great restaurants and the downstairs bakery are a great benefit
10.0 / 10.0Outstanding·Apr 2025
We had the most amazing stay in Ashland at the Urban Gypsy Loft. Alisha was a wonderful host and her loft is absolutely adorable. The beds were big and SO comfortable. Perfect walking distance through the Historic District. Can't wait to visit again some day.
$$$$
Top rated by guests
9.8Outstanding
(7 Ratings)
"Property is well placed for walking to the theater's, restaurants and core town downtown shops. "
Matt S.Don't miss out! Price and availability may change
