Find Hotels with a Pool in Ashland, OR

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Check availability on Ashland Hotels with a Pool

Tonight
Dec 24 - Dec 25
Tomorrow
Dec 25 - Dec 26
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Ashland hotels with a pool

Seasonal outdoor pool
Flagship Inn of Ashland

Flagship Inn of Ashland

Flagship Inn of Ashland
2.5 star property
Ashland
8.8 out of 10, Excellent, (1204)
"Beautiful room and friendly staff. "
United States
Jackie
The price is ￥10,011
￥11,162 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Flagship Inn of Ashland
Outdoor pool, sun loungers
Lithia Springs Resort

Lithia Springs Resort

Lithia Springs Resort
3.0 star property
Ashland
9.4 out of 10, Exceptional, (1007)
"Great stay, the room was great, very clean and bright. The breakfast buffet was awesome, also!"
United States
Denis
The price is ￥14,642
￥17,984 total
includes taxes & fees
Dec 30 - Dec 31
Lithia Springs Resort
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, (1009)
"Staff was excellent and very nice and room was clean and location is good Town is very cool 👍"
United States
Thomas
The price is ￥12,844
￥13,037 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Comfort Inn & Suites Ashland
Indoor spa tub
Stratford Inn

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1616)
"Great place to stay. The room was very nice and staff were great."
United States
Dane
The price is ￥12,646
￥14,101 total
includes taxes & fees
Dec 25 - Dec 26
Stratford Inn
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, (1003)
"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 ￥16,236
￥18,103 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Express & Suites Ashland by IHG
Lobby
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, (1005)
"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 ￥16,394
￥18,279 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, (1000)
"Staff was incredibly friendly, kept the room clean and assisted us with food recommendations."
United States
Isaac
The price is ￥17,017
￥18,975 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, (1001)
"Room very good and vintage 70s style. "
United States
James P
The price is ￥9,695
￥10,810 total
includes taxes & fees
Dec 25 - Dec 26
Timbers INN and Suites
Exterior
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
Ashland
8.8 out of 10, Excellent, (1493)
"What a great place to stay"
United States
christine
The price is ￥13,990
￥17,348 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Ashland Hills Hotel & Suites
Seasonal outdoor pool, open 7:00 AM to 8:00 PM, pool umbrellas
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

Top Ashland Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"Great place to stay. The room was very nice and staff were great."
Dane 1-night trip
Posted 3 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 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?
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, 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.