A resident black-tail deer walks the streets of Ashland, Oregon

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Our top choices for Ashland romantic hotels

Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (226 reviews)
"Great spot, close to town, cozy and comfortable!"
United States
Carey C.
The Ashland Cottage, walk to town
Coffee and/or coffee maker

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Central Point
9.8 out of 10, Exceptional, (113 reviews)
"We had such an amazing relaxing weekend at this little hidden jewel, tucked away in Central Point. "
United States
Chris A.
The price is AED 360
AED 653 total
includes taxes & fees
1 Jul - 2 Jul
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.

Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Jacksonville Historic District
9.8 out of 10, Exceptional, (80 reviews)
"The host was very helpful and responsive to questions. The location was wonderful, and the property was clean and warm. A very nice place to stay!"
United States
Sarah F.
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Smart TV, fireplace

Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (69 reviews)
"Creatively decorated and cozy. Bed a bit lumpy but overall a lovely little cottage perfectly located next to Main Street."
United States
Nancy L.
The price is AED 544
AED 1,115 total
includes taxes & fees
11 Jun - 12 Jun
Historic Bradshaw House!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Ashland Springs Hotel

Ashland Springs Hotel

10/10 Excellent
"It has a charm of a historical Hotel...Smaller rooms but, very beautiful and clean, every thing we needed for a comfortable nights stay"
Lois and Dennis 1-night trip
Posted 3 hours ago
Ashland Springs Hotel

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Frequently asked questions

Searching for romantic hotels in Ashland?
If you and your partner need some romantic time away, we've got just the ticket. Our guests also love Ashland for its popular theater scene, array of dining options, and picturesque gardens. If you want to explore the area, you might head to Allen Elizabethan Theatre, Angus Bowmer Theatre, or Oregon Shakespeare Festival. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Ashland?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Ashland: The hottest months are usually August and July with an average temp of 65°F, while the coldest months are December and January with an average of 37°F. Average annual precipitation for Ashland is 33 inches.
What is there to do in Ashland?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all that Ashland has to offer. Couples looking for a little of everything will enjoy Ashland for its theater scene, hiking, and gardens. Allen Elizabethan Theatre, Angus Bowmer Theatre, and Oregon Shakespeare Festival are worth a stop when you're out and about.
What's the best way to get to Ashland and around town during my romantic getaway?
These transportation options in Ashland might help your romantic getaway go off without a hitch: The closest major airport is Rogue Valley Intl. Airport (MFR), located 14.4 mi (23.3 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.