Find Romantic Hotels in Ashland, OR

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Pick from 26 Ashland Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Callahan's Mountain Lodge
Front of property
Callahan's Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (1022)
"Another amazing stay in the books. I stay here every time I travel down to California and couldn't have been happier to find this place. Highly recommend this place "
The price is AED 321
AED 326 total
includes taxes & fees
2 Dec - 3 Dec
Callahan's Mountain Lodge
Ashland Springs Hotel
Exterior
Ashland Springs Hotel
3.0 star property
9.4 out of 10, Exceptional, (1004)
"When we checked in we should have been told about coffee being available on the second floor in the evening. Weren’t told about the amenities that the hotel had. We’re also very disappointed that the restaurant was closed on the Monday that we were there. A full service hotel should provide dining every day "
The price is AED 570
AED 654 total
includes taxes & fees
25 Nov - 26 Nov
Ashland Springs Hotel
The Ashland Cottage, walk to town
Exterior detail
The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (188)
"Nice cozy cottage It was private and peaceful We enjoyed our stay"
The price is AED 624
AED 1,077 total
includes taxes & fees
1 Dec - 2 Dec
The Ashland Cottage, walk to town
McCall House Boutique Inn
Front of property
McCall House Boutique Inn
4.0 star property
9.2 out of 10, Wonderful, (549)
"Great location, walkable to downtown. Breakfasts were excellent and they were able to accommodate special dietary restrictions. Staff is wonderful. Loved it! "
The price is AED 637
AED 711 total
includes taxes & fees
5 Dec - 6 Dec
McCall House Boutique Inn
Oak Hill Bed & Breakfast
Front of property
Oak Hill Bed & Breakfast
3.5 star property
9.8 out of 10, Exceptional, (61)
"It was the best experience The host was supper lovely and the breakfast was amazing the room was spacious and clean It was a lovely and quiet place Definitely will come back again "
The price is AED 768
AED 856 total
includes taxes & fees
17 Dec - 18 Dec
Oak Hill Bed & Breakfast
Oak Street Cottages
Exterior
Oak Street Cottages
3.0 star property
9.4 out of 10, Exceptional, (3)
"Right in the heart of Ashland and only a block from the Oregon Shakespeare Festival this place is a gem. We stayed in the Oak Tower suite, a two story, could sleep 8 accommodation. Not only was it immaculate but it was sweetly appointed with fresh flowers, contemporary magazines, fresh fruit, Martinelli's Cider and popcorn. Master bedroom and second bedroom, large second bedroom and huge bathroom with Jacuzzi tub on the entrance level. Large living room, dining room, second bathroom and full...
Oak Street Cottages
Lithia Springs Resort
Pool
Lithia Springs Resort
3.0 star property
9.4 out of 10, Exceptional, (1003)
"The place was really cute, guilt and clean. The room was perfect and the breakfast was pretty good. "
The price is AED 534
AED 579 total
includes taxes & fees
24 Nov - 25 Nov
Lithia Springs Resort
The Maple Apartment at Tudor House Vacation Rentals
Primary bedroom
The Maple Apartment at Tudor House Vacation Rentals
9.6 out of 10, Exceptional, (138)
"Had a girls weekend. "
The Maple Apartment at Tudor House Vacation Rentals
Winchester Inn
Front of property
Winchester Inn
3.5 star property
9.8 out of 10, Exceptional, (230)
"Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay there again!"
The price is AED 419
AED 502 total
includes taxes & fees
9 Dec - 10 Dec
Winchester Inn
Plaza Inn & Suites at Ashland Creek
Front of property
Plaza Inn & Suites at Ashland Creek
3.0 star property
8.4 out of 10, Very Good, (1003)
"Always a great stay at the Plaza during Shakespeare Festival in Ashland. Safe, clean, quiet and a short walk to the theater."
The price is AED 474
AED 528 total
includes taxes & fees
24 Nov - 25 Nov
Plaza Inn & Suites at Ashland Creek
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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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, Oregon Shakespeare Festival, or Oregon Cabaret Theatre. 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.
How many romantic hotels will we find in Ashland?
Expedia has 12 romantic Ashland hotels for you both to enjoy.
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, Oregon Shakespeare Festival, and Oregon Cabaret Theatre 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.