Find Hotels with a Pool in Ashland, OR

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Check availability on Ashland Hotels with a Pool

Our top choices for Ashland hotels with a pool

Outdoor pool, sun loungers
Lithia Springs Resort

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (1005)
"Lovely room with jacuzzi bath, cozy fireplace and comfy bed. Nice tea time snacks, and beautiful outdoor areas. Very dog friendly. "
United States
hannelie
The price is ₩138,594
₩170,227 total
includes taxes & fees
Dec 16 - Dec 17
Lithia Springs Resort
Front of property - evening/night
Stratford Inn

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1599)
"Clean room, attentive staff, easy walk to downtown. "
United States
Richard
The price is ₩132,994
₩148,289 total
includes taxes & fees
Dec 16 - Dec 17
Stratford Inn
View from property
Flagship Inn of Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland
2.5 star property
Ashland
8.8 out of 10, Excellent, (1193)
"Huge room Great check in Very comfortable My 5th stay here "
United States
Michael L
The price is ₩99,745
₩111,212 total
includes taxes & fees
Dec 16 - Dec 17
Flagship Inn of Ashland
Indoor pool
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
2.5 star property
Ashland
9.2 out of 10, Wonderful, (1005)
"Very nice property with nice decor. Room much nicer than competitors I’ve stayed with . Extremely clean, super staff. Will stay here again!"
United States
Christopher
The price is ₩153,682
₩171,356 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Express & Suites Ashland by IHG
Indoor pool, sun loungers
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
Ashland
8.8 out of 10, Excellent, (1004)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is ₩123,359
₩125,209 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Comfort Inn & Suites Ashland
Seasonal outdoor pool, sun loungers
The Bard's Inn, BW Signature Collection by Best Western

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
8.6 out of 10, Excellent, (1009)
"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 ₩155,174
₩173,018 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Bard's Inn, BW Signature Collection by Best Western
Outdoor pool
Best Western Windsor Inn

Best Western Windsor Inn

Best Western Windsor Inn
2.5 star property
Ashland
9.0 out of 10, Wonderful, (1002)
"Friendly staff and very clean"
United States
Noel
The price is ₩161,070
₩179,600 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Best Western Windsor Inn
Seasonal outdoor pool
Timbers INN and Suites

Timbers INN and Suites

Timbers INN and Suites
2.0 star property
Ashland
8.6 out of 10, Excellent, (1002)
"Room very good and vintage 70s style. "
United States
James P
The price is ₩91,766
₩102,320 total
includes taxes & fees
Dec 16 - Dec 17
Timbers INN and Suites
Exterior
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
Ashland
9.0 out of 10, Wonderful, (1499)
"A very great stay with our two dogs！"
United States
Yaolin
The price is ₩132,417
₩164,211 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Ashland Hills Hotel & Suites
Free daily full breakfast
Country Willows Inn and Estate

Country Willows Inn and Estate

Country Willows Inn and Estate
4.0 star property
Ashland
9.8 out of 10, Exceptional, (33)
"Beautiful setting close to downtown. Pool is marvelous!"
United States
Carol
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.
View all properties

Hotels with pools and free breakfast in Ashland

Exterior
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
2.5 star property
Ashland
9.2 out of 10, Wonderful, (1005)
The price is ₩153,682
₩171,356 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Express & Suites Ashland by IHG
View all properties

Hotels with pools and hot tubs in Ashland

Front of property
Lithia Springs Resort

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (1005)
The price is ₩138,594
₩170,227 total
includes taxes & fees
Dec 16 - Dec 17
Lithia Springs Resort
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

Top Ashland Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"The room was clean and spacious. The best thing about our visit was chatting with Cindy over breakfast. She is a gem!!! She gave us quite a few suggestions for places to visit, and we really enjoyed chatting with her. She’s an excellent asset to your hotel and a keeper! We shall return!"
Kathy 1-night trip
Posted 6 days ago
Stratford Inn
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"Great"
Rebecca 4-night trip
Posted 6 days ago
Ashland Hills Hotel & Suites

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Frequently asked questions

What's it like visiting Ashland?
If lounging by a pool is your idea of the perfect getaway, you might want to think about welcoming Ashland, which offers 6 places to stay with pools. While you're visiting, you can explore attractions like Thomas Theatre and Oregon Shakespeare Festival, and then take it easy poolside at one of the accommodations in Ashland that guests like for their pools.
What are some hotels with pools in Ashland?
Stratford Inn: Features a children's pool, an indoor pool, and free self parking. Flagship Inn of Ashland: Offers daily, a seasonal outdoor pool, and free self parking. Country Willows Inn and Estate: Provides spa services, a seasonal outdoor pool, and full. Arden Forest Inn: Features a snack bar/deli, a seasonal outdoor pool, and free self parking.
How many pool hotels are there in Ashland?
Expedia has 6 hotels in Ashland for your poolside break.
What is there to see and do in Ashland?
Make a point to visit attractions like Lithia Park and ScienceWorks Hands-On Museum. Discover sights such as Thomas Theatre, Oregon Shakespeare Festival, and Oregon Cabaret Theatre during your stay. Ashland appeals to visitors with its picturesque gardens, popular theater scene, and array of dining options.
When is the best time to book a hotel with a pool in Ashland?
Taking into account the local weather in Ashland is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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.