The Best Hotels with a Pool in Ashland, OR from ₩101,097 in 2026

Q: What are some hotels with pools in Ashland?

Prospero's Flagship Inn : 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.

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Our top choices for Ashland hotels with a pool

An indoor swimming pool with multiple lanes, a changing room, and a sauna area.

1. Holiday Inn Express & Suites Ashland by IHG

Ashland

Blissful poolside escapes await at this hotel's indoor oasis with hot tub and fitness center.

₩150,758 total

includes taxes & fees

Nov 16 - Nov 17

An indoor swimming pool with clear water, tiled edges, and a blue mosaic border. There are lounge chairs and potted plants near the windows.

2. Stratford Inn

Siskiyou-Hargadine Historic District

Aquatic adventures await with indoor pool and hot tub escapes, perfect for year-round swimming in scenic Ashland.

₩137,862 total

includes taxes & fees

Nov 23 - Nov 24

An indoor swimming pool with a clear view of the pool area, a staircase, and seating arrangements.

3. Comfort Inn & Suites Ashland

Ashland

Relax in a 24-hour heated indoor pool sanctuary with sun loungers at this convenient, pet-friendly Ashland hotel.

₩140,404 total

includes taxes & fees

Nov 25 - Nov 26

A pool area with lounge chairs and a hot tub, surrounded by a building with a balcony and stairs.

4. Best Western Windsor Inn

Ashland

Splash into relaxation at this sun-soaked hotel pool with bubbling hot tub and mountain views.

₩166,292 total

includes taxes & fees

Nov 3 - Nov 4

A swimming pool with orange and white lounge chairs, surrounded by a fence and trees.

5. Ashland Hills Hotel & Suites

Ashland

Dive into aquatic bliss with a sparkling outdoor pool, hot tub sanctuary, and tennis courts nestled among scenic mountain views.

₩158,248 total

includes taxes & fees

Nov 19 - Nov 20

A pool area with lounge chairs and umbrellas, a small building with a balcony, and surrounding trees.

6. Lithia Springs Resort

Ashland

Mineral springs pool experience transforms relaxation in scenic gardens near Asheville's natural wonders.

₩152,420 total

includes taxes & fees

Nov 16 - Nov 17

A pool area with lounge chairs and a covered seating area.

7. The Bard's Inn, BW Signature Collection by Best Western

Historic Downtown District

Splash into a seasonal oasis with pool-side relaxation in downtown Asheville's cultural hub.

₩146,339 total

includes taxes & fees

Nov 26 - Nov 27

A poolside area with lounge chairs and umbrellas, a pool, and a view of trees and mountains.

8. Prospero's Flagship Inn

Ashland

Dive into sparkling, seasonal pool days in Ashland with mountains as your backdrop.

₩101,102 total

includes taxes & fees

Nov 1 - Nov 2

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Choose what matters most at hotels with a pool in Ashland

Breakfast included

Hot tub

Hotels with pools and free breakfast in Ashland

A Holiday Inn Express hotel with a two-story structure, a parking lot, and a landscaped area with shrubs and a tall tree.

Holiday Inn Express & Suites Ashland by IHG

Ashland

₩150,758 total

includes taxes & fees

Nov 16 - Nov 17

A spacious lobby with a reception desk, seating area, and large windows.

The Bard's Inn, BW Signature Collection by Best Western

Historic Downtown District

₩146,339 total

includes taxes & fees

Nov 26 - Nov 27

View all properties

Hotels with pools and hot tubs in Ashland

Holiday Inn Express & Suites Ashland by IHG

Ashland

₩150,758 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Top Ashland Hotel Reviews

Comfort Inn & Suites Ashland

10/10 Excellent

"This was our second stay at Comfort Inn & Suites in Ashland. We’ve been so impressed with the friendly, professional staff and cleanliness of the hotel in general, we recommended it to some friends!"

The Bard's Inn, BW Signature Collection by Best Western

8/10 Good

"We booked Jere because everything else was taken that was in downtown. The hotel is ok. Breakfast was decent with some variety in terms of protein and fresh fruit. The tvs are out dated so we couldn’t watch Netflix and the property is spread out over 4 buildings at 3 different intersections."

Ashland Motel - Oregon

8/10 Good

"Rooms are clean and have window ac units. Bathroom is a decent size and shower is amply large. Free parking available. No housekeeping offered for first four days and rarely is anyone in the office. On our last day, someone knocked on the door and asked us if we needed housekeeping, but we were leaving the next day so that wasn’t helpful. Desk area is useful and there is an extension cord with multiple outlets by the desk."

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 10 places to stay with pools. While you're visiting, you can explore attractions like Allen Elizabethan Theatre and Angus Bowmer 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?

Prospero's Flagship Inn: 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.

How many pool hotels are there in Ashland?

Expedia has 10 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, Angus Bowmer 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.

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Find Hotels with a Pool in Ashland, OR

Change your mind

Treat yourself

Be picky

Check availability on Ashland Hotels with a Pool

Our top choices for Ashland hotels with a pool

1. Holiday Inn Express & Suites Ashland by IHG

2. Stratford Inn

3. Comfort Inn & Suites Ashland

4. Best Western Windsor Inn

5. Ashland Hills Hotel & Suites

6. Lithia Springs Resort

7. The Bard's Inn, BW Signature Collection by Best Western

8. Prospero's Flagship Inn

9. Timbers INN and Suites

10. Palm Cottages

Choose what matters most at hotels with a pool in Ashland

Hotels with pools and free breakfast in Ashland

Holiday Inn Express & Suites Ashland by IHG

Hotels with pools and hot tubs in Ashland

Holiday Inn Express & Suites Ashland by IHG

Top Ashland Hotel Reviews

Comfort Inn & Suites Ashland

Frequently asked questions

Explore a world of travel with Expedia