Search Chalets in Ashland

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Chalets in Ashland

No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

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

Lodge in Ashland

3.0 star property
8.8 out of 10, Excellent, (1170)
"Loved our visit there, staff was top notch"
United States
Michael
The price is SAR 377
SAR 439 total
includes taxes & fees
9 Dec - 10 Dec
Callahan's Mountain Lodge
Exterior
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

2.5 star property
9.2 out of 10, Wonderful, (1013)
"Clean and friendly staff"
United States
Liza Rene
The price is SAR 318
SAR 355 total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express & Suites Ashland by IHG
Garden
Lithia Springs Resort

Bed & Breakfast in Ashland

3.0 star property
9.4 out of 10, Exceptional, (1013)
"Our stay was magical!"
United States
Maryah
Lithia Springs Resort
Exterior
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3.0 star property
9.0 out of 10, Wonderful, (1519)
"I love staying here because the decoration is so great and the food and service is phenomenal."
United States
Roxane
The price is SAR 313
SAR 386 total
includes taxes & fees
2 Jan - 3 January 2026
Ashland Hills Hotel & Suites
Exterior detail
Stratford Inn

Stratford Inn

2.5 star property
9.4 out of 10, Exceptional, (1605)
"Friendly staff, nice hot tub.clean room."
United States
Ann
The price is SAR 338
SAR 376 total
includes taxes & fees
9 Dec - 10 Dec
Stratford Inn
Land view from property
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 star property
8.8 out of 10, Excellent, (1186)
"The room was clean and the staff was very friendly. Would definitely stay again."
Canada
Susan
The price is SAR 245
SAR 273 total
includes taxes & fees
9 Dec - 10 Dec
Flagship Inn of Ashland
Front of property - evening/night
Ashland Springs Hotel

Ashland Springs Hotel

3.0 star property
9.2 out of 10, Wonderful, (1016)
"Always a great place to stay in downtown. This historic hotel has lots of charm and rooms with downtown view are fun."
United States
aurora
The price is SAR 399
SAR 501 total
includes taxes & fees
10 Dec - 11 Dec
Ashland Springs Hotel
Exterior
Timbers INN and Suites

Motel in Ashland

2.0 star property
8.6 out of 10, Excellent, (1010)
"It was a great overall experience and we liked the accessibility to main Ashland. Comfy bed, nice shower. "
United States
Sequoyah
The price is SAR 236
SAR 264 total
includes taxes & fees
16 Dec - 17 Dec
Timbers INN and Suites
Exterior
Best Western Windsor Inn

Best Western Windsor Inn

2.5 star property
9.0 out of 10, Wonderful, (1011)
"Location was convenient for traveling thru Ashland, but not so convenient if you wish to attend the Festival as you have to drive into town. "
United States
Janet
The price is SAR 409
SAR 456 total
includes taxes & fees
9 Dec - 10 Dec
Best Western Windsor Inn
Terrace/patio
The Bard's Inn, BW Signature Collection by Best Western

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

2.5 star property
8.6 out of 10, Excellent, (1008)
"The Bards Inn is lovely with each room themed after a Shakespe Play. Location is excellent just at the top of Main St. I can highly recommend this hotel"
United States
Suzanne
The price is SAR 394
SAR 439 total
includes taxes & fees
14 Dec - 15 Dec
The Bard's Inn, BW Signature Collection by Best Western
Aerial view
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 star property
8.6 out of 10, Excellent, (1027)
"Clean, great pool, super friendly staff. "
United States
Scott
The price is SAR 318
SAR 322 total
includes taxes & fees
1 Jan - 2 January 2026
Comfort Inn & Suites Ashland
Front of property
Winchester Inn

Inn in Historic Downtown District

3.5 star property
9.6 out of 10, Exceptional, (258)
"Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!"
United States
Laura
The price is SAR 999
SAR 1,170 total
includes taxes & fees
24 Dec - 25 Dec
Winchester Inn
Free daily full breakfast
Country Willows Inn and Estate

Bed & Breakfast in Ashland

4.0 star property
9.8 out of 10, Exceptional, (33)
"Beautiful setting close to downtown. Pool is marvelous!"
United States
Carol
Country Willows Inn and Estate
Terrace/patio
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3.0 star property
8.8 out of 10, Excellent, (1010)
"Desk staff was very nice room clean and quiet"
United States
Richard
Plaza Inn & Suites at Ashland Creek
Exterior
Green Springs Inn

Resort in Ashland

2.0 star property
9.4 out of 10, Exceptional, (108)
"Definitely not what we expected drove 4 miles up the road and stayed at a way nicer place Hyatt Lake Resort"
United States
Joseph
The price is SAR 347
SAR 448 total
includes taxes & fees
16 Dec - 17 Dec
Green Springs Inn
Exterior
Ashland Motel - Oregon

Motel in Ashland

2.0 star property
7.8 out of 10, Good, (216)
"Great service "
United States
James
The price is SAR 257
SAR 287 total
includes taxes & fees
3 Dec - 4 Dec
Ashland Motel - Oregon
Exterior
Chateau Herbe ~ Athens Room

Castle in Ashland

9.8 out of 10, Exceptional, (25)
"Such a beautiful home and grounds. Large bedroom and attached bath (We stayed in the Athen Room). Enjoyed the large balcony off of our room. Very comfortable and pleasant stay!"
United States
Karen
The price is SAR 372
SAR 549 total
includes taxes & fees
28 Dec - 29 Dec
Chateau Herbe ~ Athens Room
View from property
Ashland Commons Hostel

Ashland Commons Hostel

2.0 star property
9.4 out of 10, Exceptional, (50)
"Nice hostel and clean rooms"
United States
EASWARAMOORTHI
The price is SAR 68
SAR 227 total
includes taxes & fees
14 Dec - 15 Dec
Ashland Commons Hostel
Property entrance
The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2.0 star property
9.6 out of 10, Exceptional, (95)
"A lovely spot to stay! Our room was beautifully furnished and cozy with a historic charm. The outdoor balcony was a great way to wake up with a cup of coffee. Within walking distance of the theaters and downtown. "
United States
Matthew
The Peerless Hotel by WanderLodges
Exterior
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Cottage in Ashland

10.0 out of 10, Exceptional, (18)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is SAR 296
SAR 666 total
includes taxes & fees
2 Jan - 3 January 2026
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ashland Hotel Reviews

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"I love staying here because the decoration is so great and the food and service is phenomenal."
Roxane 1-night trip
Posted 1 day ago
Ashland Hills Hotel & Suites