Ashland cottage rentals

Select from 21 cottage rentals in Ashland that offer a quiet, cozy retreat amid the sounds and sights of nature. Search for Vrbo’s cottages in some of the most popular areas such as Historic Railroad District, Siskiyou-Hargadine Historic District and Skidmore Academy Historic District.

One of the only things better than spending your trip in a quaint cottage rental in Ashland is getting it for a fantastic price. Keep an eye out for any properties that offer discounts to guests who stay a week. Some properties offer better discounts for stays of a month or longer. You can also use Vrbo’s price filter to find cottages within your budget.

With temperatures ranging from 28ºF (-2ºC) to 53ºF (12ºC), November is when most people book a cottage rental in Ashland. Since it’s the busiest time of year, it’s a good idea to secure your stay well in advance. Alternatively, check out the off-season for a more relaxing Jackson County escape.

At Vrbo, we redefine your cottage rental experience in Ashland with accommodations that provide more than just a place to sleep. Enjoy your morning coffee with the sunrise or relax at the end of the day with the setting sun — great scenery always adds that little something extra to your vacation. Use our filter tools to tailor your search and find the kind of views you love to look at.

For a refreshing change of scenery, it’s tough to beat our lakeside cottage rentals. Use our “Location” filter tool and then click on “Lake” to see if you can find any cozy stays that’ll put you near the water in Ashland. Spend your days chasing adventures or simply enjoy admiring beautiful sunrises and sunsets shimmering across the lake.

Oregon Shakespeare Festival is one of the many well-known attractions in Ashland. Stay in a cottage rental in this destination and give yourself plenty of time to explore other highlights, including Mount Ashland Ski Area and Lithia Park. They’re all perfect for families!

Booking your cottage rental with Vrbo means you’ll have the whole place for your exclusive use — your own private sanctuary, without any distractions or interruptions from others. Also, our One Key™ loyalty program lets you collect OneKeyCash™* and spend it on eligible bookings on Vrbo, Expedia and Hotels.com. What’s more, our easy payment and cancellation policies give you the freedom to amend your plans if necessary. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo, Expedia and Hotels.com.