Historic Downtown District vacation rentals
We found 84 vacation rentals — enter your dates for availability
Discover a selection of 12 apartments, 10 cottages, and other vacation rentals in Historic Downtown District that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation rentals have the amenities you expect for your stay, which might include air conditioning and a pool. What you'll find is a rental that has what everyone needs, including places that are non-smoking or accessible.
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Find properties near top attractions in Historic Downtown District
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![Ashland is probably best known for the Tony Award-winning Oregon Shakespeare Festival, which I highly recommend checking out if you're in to Shakespeare plays.
The statue in the photo is actually a guy in a Shakespearean costume collecting contributions toward a permanent statue of the Bard in Ashland.
#WeekendGetaway](https://mediaim.expedia.com/destination/2/e7d42a6fce65f5ab7a72ba316bf31a64.jpg)
Oregon Shakespeare Festival
Find the best place to stay - Historic Downtown District
Photo gallery for Ashland Escape: Downtown & Pet Friendly
![Master bedroom (King bed)](https://images.trvl-media.com/lodging/99000000/98260000/98255900/98255807/d63d6a39.jpg?impolicy=resizecrop&rw=355&ra=fit)
Ashland Escape: Downtown & Pet Friendly
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.8 out of 10
exceptional
(11 reviews)
Top rated rentals - Historic Downtown District
Photo gallery for In the historic railroad district, walking distance to all the best of Ashland!
![Heritage Home - front view](https://images.trvl-media.com/lodging/28000000/27930000/27921400/27921331/bd2c614b.jpg?impolicy=resizecrop&rw=355&ra=fit)
A pleasure to return to stay
10 out of 10
exceptional
(159 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value