Find Romantic Hotels in Ashland, OR

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Ashland Romantic Hotels

Tonight
21 Jul - 22 Jul
Tomorrow
22 Jul - 23 Jul
This weekend
25 Jul - 27 Jul
Next weekend
1 Aug - 3 Aug

Top Ashland Romantic Hotels

Callahan's Mountain Lodge
Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio

Callahan's Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (1155)
"We really enjoyed our stay!"
The price is £111
includes taxes & fees
23 Jul - 24 Jul
Callahan's Mountain Lodge
Ashland Springs Hotel
Garden

Ashland Springs Hotel

3.0 star property
9.4 out of 10, Exceptional, (1003)
"Great place to stay when attending a show at the OSF."
The price is £214
includes taxes & fees
30 Jul - 31 Jul
Ashland Springs Hotel
The Ashland Cottage, walk to town
Interior

The Ashland Cottage, walk to town

10.0 out of 10, Exceptional, (200)
"Loved it."
The price is £221
includes taxes & fees
30 Jul - 31 Jul
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, (565)
"What a phenomenal experience! Our stay was lovely, the staff was so kind and friendly, everything was in walking distance and the Shakespeare experience was incredible. We can’t wait to come back. Thank you for a wonderful stay at the Inn. "
McCall House Boutique Inn
Oak Hill Bed & Breakfast
Coffee service

Oak Hill Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (63)
"We booked last minute..loved the room it was clean and comfy. The owners were fabulous and the breakfast was heavenly. "
The price is £205
includes taxes & fees
4 Aug - 5 Aug
Oak Hill Bed & Breakfast
Oak Street Cottages
Cottage, Private Bathroom (Oak Hideaway) | Terrace/patio

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
Front of property

Lithia Springs Resort

3.0 star property
9.4 out of 10, Exceptional, (1003)
"Loved coming here because it is pet friendly. "
Lithia Springs Resort
The Maple Apartment at Tudor House Vacation Rentals
Property grounds

The Maple Apartment at Tudor House Vacation Rentals

9.6 out of 10, Exceptional, (143)
"Lovely apartment for my daughter and I to stay while visiting Ashland family. Loved the watercolor paintings by the owners mother and outside courtyard. Also nice we could charge our EV in the driveway"
The Maple Apartment at Tudor House Vacation Rentals
Winchester Inn
Bar (on property)

Winchester Inn

3.5 star property
9.6 out of 10, Exceptional, (248)
"Beautiful property, really comfortable bed, pillows and sheets! "
The price is £189
includes taxes & fees
28 Jul - 29 Jul
Winchester Inn
Plaza Inn & Suites at Ashland Creek
Outdoor dining

Plaza Inn & Suites at Ashland Creek

3.0 star property
8.6 out of 10, Excellent, (1002)
"Very clean, quiet, great location, good breakfast"
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.

Top Ashland Hotel Reviews

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
" helpful with laptop sign in. allowed for personal ice chest to be stored in hours after checking out. ever courteous and helpful. "
Darlene 2-night trip
Posted 2 days ago
Flagship Inn of Ashland

Frequently asked questions

Searching for romantic hotels in Ashland?
If you and your partner need a romantic escape, we'd like to help you plan for it. Our guests also love Ashland for its popular theatre 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'd like to stay close to a certain attraction, you can sort properties by neighbourhood or distance to top sights, so you and your partner will get to see everything on your list.
What's the best hotel for a romantic getaway to Ashland?
Callahan's Mountain Lodge is a favourite lodge for couples, and features an al fresco restaurant and wedding services. Other good options for your romantic getaway include Lithia Springs Resort and Ashland Springs Hotel.
How many romantic hotels should we expect to 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, take a look at these details about year-round temperatures in Ashland: The hottest months are usually August and July, with an average temperature of 18°C, while the coldest months are December and January, with an average of 3°C. Average annual precipitation for Ashland is 850 mm.
What is there to do in Ashland?
There's nothing better than experiencing 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 theatre 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 trip go off without a hitch: The closest major airport is in Medford, OR (MFR-Rogue Valley Intl.), located 14.4 mi (23.3 km) from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.