Find Hotels with a Pool in Ashland, OR

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Check availability on Ashland Hotels with a Pool

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Ashland hotels with a pool

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, (1626)
"Great place to stay. The room was very nice and staff were great."
United States
Dane
The price is ￥12,682
￥14,141 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Stratford Inn
Outdoor pool, sun loungers
Lithia Springs Resort

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (1000)
"Great stay, the room was great, very clean and bright. The breakfast buffet was awesome, also!"
United States
Denis
The price is ￥14,685
￥18,037 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lithia Springs Resort
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, (1207)
"Beautiful room and friendly staff. "
United States
Jackie
The price is ￥10,042
￥11,197 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Flagship Inn of Ashland
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, (1010)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is ￥12,662
￥12,852 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Comfort Inn & Suites 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, (1000)
"Friendly staff, easy, check-in, close parking, clean rooms, quiet. Good breakfast. Hot cakes, bacon, sausage, eggs, cinnamon rolls, yogurt everything you could want."
United States
Tiea
The price is ￥16,283
￥18,157 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Holiday Inn Express & Suites Ashland by IHG
Exterior
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
Ashland
8.8 out of 10, Excellent, (1500)
"What a great place to stay"
United States
christine
The price is ￥14,030
￥17,398 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Ashland Hills Hotel & Suites
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, (1000)
"Courteous staff. Room was clean, and nice and hot for the winter cold outside. Plus, it's right next door to a great little pizza place!"
United States
Kevin
The price is ￥9,723
￥10,841 total
includes taxes & fees
Dec 30 - Dec 31
Timbers INN and 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
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, (1001)
"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 ￥16,441
￥18,331 total
includes taxes & fees
Jan 11 - Jan 12, 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, (1001)
"Staff was incredibly friendly, kept the room clean and assisted us with food recommendations."
United States
Isaac
The price is ￥17,066
￥19,029 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Best Western Windsor Inn
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
"Absolutely loved this place. I’m sad we only stayed one night. Lovely small boutique hotel with elevator and luggage carts (which was a nice surprise). Every staff member we spoke to was very kind (shoutout to Cindy). The room was clean and inviting. The indoor heated pool and hot tub are divine. Already want to plan another trip here to spend more time! "
Bernadette 1-night trip
Posted 4 days ago
Stratford Inn

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 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. 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, 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.