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Check availability on Ashland Romantic Hotels

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15

Our top choices for Ashland romantic hotels

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is ￥19,264
￥41,683 total
includes taxes & fees
Nov 4 - Nov 5
Barclay Klum House by WanderLodges
A deck with a fire pit, outdoor seating, and a view of the countryside.

2. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
The price is ￥28,787
￥61,043 total
includes taxes & fees
Nov 2 - Nov 3
Grandview of Ashland
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

3. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is ￥25,383
￥51,140 total
includes taxes & fees
Nov 2 - Nov 3
The Mountain Ave House by WanderLodges
A garden with a red pergola, a stone fountain, and purple flowers.

4. Arden Forest Inn

Arden Forest Inn
4.0 star property
Ashland
9.8 out of 10, Exceptional, (115 reviews)
"Terrific in all aspects. Look forward to returning."
United States
Thomas
The price is ￥21,567
￥24,048 total
includes taxes & fees
Nov 2 - Nov 3
Arden Forest Inn
A two-story building with a wooden facade, large windows, and a front porch with chairs.

5. The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
2.0 star property
Historic Railroad District
9.6 out of 10, Exceptional, (118 reviews)
"My room was clean, bed was comfortable. It was really nice and central to restaurants, coffee shops and downtown. It was nice having a door code instead of keys etc. would stay here again"
Canada
Lindsay
The price is ￥14,263
￥24,511 total
includes taxes & fees
Dec 1 - Dec 2
The Peerless Hotel by WanderLodges
A large, two-story house with a wrap-around porch and a steeply pitched roof.

6. Winchester Inn

Winchester Inn
3.5 star property
Historic Downtown District
9.6 out of 10, Exceptional, (291 reviews)
"Amazing breakfasts, friendly staff, best location"
United States
Ellen
The price is ￥21,046
￥25,982 total
includes taxes & fees
Nov 30 - Dec 1
Winchester Inn
A Victorian-style building with ornate architectural details, large windows, and a red door.

7. McCall House Boutique Inn

McCall House Boutique Inn
4.0 star property
Historic Downtown District
9.6 out of 10, Exceptional, (619 reviews)
"All good; would stay again. Great breakfast too"
United States
Elizabeth
The price is ￥27,725
￥30,914 total
includes taxes & fees
Dec 1 - Dec 2
McCall House Boutique Inn
An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.

8. Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1,796 reviews)
"Nice little hotel that was well decorated for the holiday."
United States
Thomas
The price is ￥14,733
￥16,427 total
includes taxes & fees
Nov 9 - Nov 10
Stratford Inn
A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

9. Ashland Commons Hostel

Ashland Commons Hostel
2.0 star property
Ashland
9.4 out of 10, Exceptional, (75 reviews)
"Great place to stay. Excellent location."
United States
Sam
The price is ￥10,530
￥11,741 total
includes taxes & fees
Nov 2 - Nov 3
Ashland Commons Hostel
A two-story house with a porch, surrounded by a well-maintained garden with various flowers and shrubs.

10. Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn
3.5 star property
Skidmore Academy Historic District
9.4 out of 10, Exceptional, (66 reviews)
"I have stayed in many bed and breakfasts over the years and this one ranks a perfect 10! Very clean,very friendly hosts, the absolute best breakfast of any B & B I've been to. If I'm going through Ashland in the future, this is my go to lodging. This felt like home! Hosts also were extremely helpful and knowledgeable about local dining. "
United States
Kim
The price is ￥40,966
￥45,677 total
includes taxes & fees
Nov 2 - Nov 3
Abigail’s Bed & Breakfast Inn
An outdoor patio area with tables and chairs, string lights, and potted plants.

11. Ashland Springs Hotel

Ashland Springs Hotel
3.0 star property
Historic Downtown District
9.2 out of 10, Wonderful, (1,002 reviews)
"Location is perfect for Ashland."
United States
Duff
The price is ￥14,744
￥18,886 total
includes taxes & fees
Dec 1 - Dec 2
Ashland Springs Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

12. Palm Cottages

Palm Cottages
2.5 star property
Ashland
9.2 out of 10, Wonderful, (233 reviews)
"Palm Cottages is a clean and wonderful boutique hotel on the outskirts of downtown Ashland. We only stayed one night but we will definitely be back again some day. Thank you 🙏"
United States
Eric
The price is ￥31,982
￥35,659 total
includes taxes & fees
Nov 2 - Nov 3
Palm Cottages
An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

13. Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
3.0 star property
Ashland
9.0 out of 10, Wonderful, (1,001 reviews)
"Very nicece hotel and perfect location for walking and exploring Ashland."
United States
Heather
The price is ￥18,292
￥20,395 total
includes taxes & fees
Nov 1 - Nov 2
Plaza Inn & Suites at Ashland Creek
A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

14. Timbers INN and Suites

Timbers INN and Suites
2.0 star property
Ashland
8.8 out of 10, Excellent, (1,001 reviews)
"Our room was very clean and comfortable and our staff interaction was great. We’ll definitely stay here again when we come to Ashland."
United States
Sarah
The price is ￥9,921
￥11,062 total
includes taxes & fees
Nov 18 - Nov 19
Timbers INN and Suites
A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

15. Prospero's Flagship Inn

Prospero's Flagship Inn
2.5 star property
Ashland
8.4 out of 10, Very good, (1,483 reviews)
"We enjoyed our stay very much. The location was good; the staff great and our room was very nice"
United States
Mary
The price is ￥9,758
￥10,880 total
includes taxes & fees
Nov 5 - Nov 6
Prospero's Flagship Inn
A spacious lobby with a reception desk, seating area, and large windows.

16. The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western
2.5 star property
Historic Downtown District
8.4 out of 10, Very good, (1,000 reviews)
"Location is very convenient to nice walks, restaurants and shops."
United States
Thomas
The price is ￥14,970
￥16,691 total
includes taxes & fees
Dec 1 - Dec 2
The Bard's Inn, BW Signature Collection by Best Western
A hotel room with a desk, laptop, two beds, and a round mirror.

17. Ashland Motel - Oregon

Ashland Motel - Oregon
2.0 star property
Ashland
8.0 out of 10, Very good, (251 reviews)
"Clean, basic room that is walking distance to downtown Ashland."
United States
Madrik A.
The price is ￥10,046
￥11,202 total
includes taxes & fees
Nov 9 - Nov 10
Ashland Motel - Oregon
A dining area with a wooden table and chairs, a potted plant, and a window with blinds.

18. Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
2.0 star property
Ashland
7.4 out of 10, Good, (1,000 reviews)
"Good location, good value."
United States
Toby
The price is ￥10,879
￥12,130 total
includes taxes & fees
Nov 18 - Nov 19
Cedarwood Inn of Ashland
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

19. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is ￥25,210
￥54,285 total
includes taxes & fees
Nov 22 - Nov 23
Savage Upon Siskiyou
A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

20. Country Willows Inn and Estate

Country Willows Inn and Estate
4.0 star property
Ashland
9.8 out of 10, Exceptional, (45 reviews)
"A beautiful serene landscape compliments the beautifully decorated and very comfy rooms. Beds and pillows were divine. Breakfast was epicurean."
United States
Diane
The price is ￥25,965
￥26,354 total
includes taxes & fees
Nov 1 - Nov 2
Country Willows Inn and Estate
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

Lithia Springs Resort

Lithia Springs Resort

10/10 Excellent
"This place feels like my home away from home! I come twice a month and love the private in room tubs and the pool and hot tub too! Always very clean and the staff are great!"
Belinda 1-night trip
Posted 1 hour ago
Lithia Springs Resort

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.