Find Hotels with a Pool in Ashland, OR

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Check availability on Ashland Hotels with a Pool

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Ashland Hotels with a Pool

Exterior
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3.0 star property
Ashland
9.0 out of 10, Wonderful, (1487)
"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
Indoor pool
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, (1013)
"Clean and friendly staff"
United States
Liza Rene
The price is SAR 342
SAR 382 total
includes taxes & fees
19 Dec - 20 Dec
Holiday Inn Express & Suites Ashland by IHG
Outdoor pool, sun loungers
Lithia Springs Resort

Lithia Springs Resort

3.0 star property
Ashland
9.4 out of 10, Exceptional, (1014)
"Our stay was magical!"
United States
Maryah
Lithia Springs Resort
View from property
Flagship Inn of Ashland

Flagship Inn of Ashland

2.5 star property
Ashland
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 256
SAR 286 total
includes taxes & fees
7 Dec - 8 Dec
Flagship Inn of Ashland
Indoor pool, sun loungers
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 star property
Ashland
8.6 out of 10, Excellent, (1000)
"Clean, great pool, super friendly staff. "
United States
Scott
The price is SAR 298
SAR 302 total
includes taxes & fees
4 Jan - 5 January 2026
Comfort Inn & Suites Ashland
Front of property - evening/night
Stratford Inn

Stratford Inn

2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1589)
"Friendly staff, nice hot tub.clean room."
United States
Ann
The price is SAR 338
SAR 377 total
includes taxes & fees
8 Dec - 9 Dec
Stratford Inn
Free daily full breakfast
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
Outdoor pool
Best Western Windsor Inn

Best Western Windsor Inn

2.5 star property
Ashland
9.0 out of 10, Wonderful, (1000)
"Friendly upon check in and our room was clean and sufficient. "
Canada
Lynn
The price is SAR 409
SAR 456 total
includes taxes & fees
10 Dec - 11 Dec
Best Western Windsor Inn
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

2.5 star property
Historic Downtown District
8.6 out of 10, Excellent, (1010)
"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
2 Jan - 3 January 2026
The Bard's Inn, BW Signature Collection by Best Western
Seasonal outdoor pool
Timbers INN and Suites

Timbers INN and Suites

2.0 star property
Ashland
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
17 Dec - 18 Dec
Timbers INN and Suites
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

Stratford Inn

Stratford Inn

10/10 Excellent
"My daughter recommended Stratford Inn and I'm glad I took her advice. The desk clerk was helpful as well as professional. My room was on the 2nd floor, and he offered a cart, similar to those at airports, to more easily move my belongings upstairs via the elevator. My bed was comfortable and the room clean and well appointed. Breakfast was varied and healthy, and checkout a breeze."
Linda K 1-night trip
Posted 22 hours ago
Stratford Inn

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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 Allen Elizabethan Theatre and Thomas Theatre, 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?
Flagship Inn of Ashland: Features daily, a seasonal outdoor pool, and free self parking. Stratford Inn: Offers a children's pool, an indoor 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. Come stay at our farmhouse! A place to integrate all the beauty surrounding you!: Offers complimentary wireless internet access, a pool, and kitchens.
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 Allen Elizabethan Theatre, Thomas Theatre, and Oregon Shakespeare Festival 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.