Hotels with Pool & Resorts in Ashland from NZ$113

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Check availability on Ashland Hotels with Pool

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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, (1630)
"Great place to stay. The room was very nice and staff were great."
United States
Dane
Stratford Inn
Outdoor pool, pool 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 NZ$198
includes taxes & fees
4 Jan - 5 Jan 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, (1209)
"Beautiful room and friendly staff. "
United States
Jackie
The price is NZ$113
includes taxes & fees
1 Jan - 2 Jan 2026
Flagship Inn of Ashland
Indoor pool, pool loungers
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
Ashland
8.8 out of 10, Excellent, (1012)
"We took advantage of the jacuzzi and the daily breakfast bar."
United States
Kirsten
The price is NZ$141
includes taxes & fees
25 Jan - 26 Jan 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 NZ$200
includes taxes & fees
10 Jan - 11 Jan 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 NZ$191
includes taxes & fees
1 Jan - 2 Jan 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 NZ$119
includes taxes & fees
1 Jan - 2 Jan 2026
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, pool 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 NZ$202
includes taxes & fees
11 Jan - 12 Jan 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 NZ$209
includes taxes & fees
11 Jan - 12 Jan 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

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
"Room was clean and had what I needed "
Marian 1-night trip
Posted 1 day ago
Flagship Inn of Ashland

Frequently asked questions

What's it like visiting Ashland?
If laying by the 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 here, you can explore sights such as Allen Elizabethan Theatre and Oregon Shakespeare Festival, and then relax and unwind poolside at one of the accommodation options 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 should I expect to find 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 such as 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 theatre scene and array of dining options.
When is the best time to book a hotel with a pool in Ashland?
Taking the local weather in Ashland into account can help you maximise your time at the pool during your trip. The hottest months are usually August and July, with an average temperature of 18°C, while the coldest months are December and January, with an average of 3°C. Average annual precipitation for Ashland is 850 mm.