Romantic Hotels in Ashland, OR

Name: Winchester Inn
Price range: $186 total

Dec 26 - Dec 27

Tonight

Dec 27 - Dec 28

Tomorrow night

Featured Ashland Romantic Getaways & Hotels

Free Cancellation

Reserve now, pay when you stay

$117 nightly

$119 total

Dec 30 - Dec 31

Total with taxes and fees

At Callahan's Mountain Lodge, guests have access to a gym, free WiFi in public areas, and a conference center. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with luggage storage, and answer any questions about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Other amenities at this hot springs lodge include a business center, coffee/tea in a common area, and a microwave in a common area.

Breakfast included

Pet friendly

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$123 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Guests staying at Ashland Springs Hotel enjoy access to a full-service spa, a gym, and a sauna. A stay here includes free parking. The front desk is staffed 24/7 to help with securing valuables, dry cleaning/laundry, and concierge services. Other amenities at this spa hotel include free WiFi in public areas, meeting rooms, and a conference center.

Spa

Pet friendly

$257 nightly

$287 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Guests staying at this cottage have access to barbecue grills and a garden.

Kitchen

Air conditioning

$164 nightly

$183 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

McCall House Boutique Inn features free WiFi in public areas, a business center, and coffee in a common area. You can take advantage of free parking if you drive. The front desk has multilingual staff that can help with concierge services and luggage storage. Other amenities at this hot springs bed & breakfast include a microwave in a common area, a refrigerator in a common area, and a computer station.

Breakfast included

Parking included

Oak Street Cottages features free WiFi in public areas and a picnic area. If you drive, put free parking to good use. This cottage also has barbecue grills.

Pet friendly

Parking included

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$126 total

Dec 30 - Dec 31

Total with taxes and fees

Lithia Springs Resort offers an outdoor pool, free WiFi in public areas, and a hot tub. You can take advantage of free parking if you drive. The front desk has multilingual staff that can help with dry cleaning/laundry and concierge services. Additional amenities include meeting rooms, a business center, and coffee/tea in a common area.

Pool

Hot Tub

The Maple Apartment at Tudor House Vacation Rentals

This apartment is a smoke-free apartment building.

Kitchen

Air conditioning

$167 nightly

$186 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Guests of Winchester Inn enjoy free WiFi in public areas, a meeting room, and free newspapers. If you plan to drive, free parking is available. Front-desk staff can assist with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a terrace, a gift shop, and a garden.

Breakfast included

Parking included

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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.

Couples getaways in Ashland

Want to surprise your other half with a dreamy weekend getaway? Or maybe you're hoping to impress that special someone with a night in a luxury resort? Whatever kind of romantic vacation you're looking for, there's sure to be something that sets your heart aflutter in Ashland.

Romantic places to visit in Ashland

Planning to take your sweetheart out on a romantic date? These unique attractions will help add to the chemistry:

In the mood to get out and explore every part of this neighborhood with your love? Lithia Park is an ideal place to start.
Oregon Cabaret Theatre is another spot worth seeing together. Make sure you take your camera — you'll want to remember these priceless moments.
Soak up more of the area's culture by visiting Howard Prairie Lake. It's a well-known attraction and is just a stone's throw away.
If you have a bit of extra time up your sleeve, make some new memories at Emigrant Lake. With your main squeeze by your side, they're guaranteed to last forever.

Ashland hotels essential information

Accommodation	780 hotels
Lowest Price	$119
Highest Price	$287
Popular hotels	Callahan's Mountain Lodge, Ashland Springs Hotel, The Ashland Cottage, walk to town, McCall House Boutique Inn, Oak Street Cottages, Lithia Springs Resort, The Maple Apartment at Tudor House Vacation Rentals, Winchester Inn