Highly Rated Hotels With Pool in Ashland | Expedia

A deer on a road with vegetation on the sides.

Check availability on Ashland Hotels with a Pool

Tonight

Oct 16 - Oct 17

Tomorrow

Oct 17 - Oct 18

This weekend

Oct 16 - Oct 18

Next weekend

Oct 23 - Oct 25

Our top choices for Ashland hotels with a pool

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

A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

An outdoor patio with lounge chairs and a table, surrounded by autumn foliage and a view of mountains.

A spacious living room with a high ceiling, large windows, and a mix of seating arrangements including a sofa and chairs.

1. 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.

$121 nightly

$135 total

Nov 4 - Nov 5

Total with taxes and fees

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

An outdoor patio with a fire pit, seating, and potted plants.

A lobby with leather sofas, a rug, and lamps.

A restaurant with wooden chairs and tables, large windows, and a dragon sculpture.

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.

$86 nightly

$96 total

Nov 4 - Nov 5

Total with taxes and fees

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

A hotel room with a large bed, two bedside tables with lamps, a wooden headboard, a framed picture on the wall, a mirror above the sink, and striped carpeting.

A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

A hotel entrance with a sign, a pedestrian crossing sign, and a road with trees.

3. Prospero's Flagship Inn

Ashland

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

$56 nightly

$62 total

Oct 26 - Oct 27

Total with taxes and fees

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

Exterior

A patio with stone flooring, wooden chairs, and a wooden fence in the background.

A hotel room with a large bed, a separate sitting area, a large bathtub, and a flat-screen TV.

4. Best Western Windsor Inn

Ashland

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

$106 nightly

$118 total

Oct 31 - Nov 1

Total with taxes and fees

A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

A modern hotel lobby with a leather sofa, a coffee table, a patterned rug, a reception desk, and a wall-mounted snack station.

A covered outdoor seating area with benches and potted plants.

A hotel room with a large bed, a desk, and a window with curtains.

5. Timbers INN and Suites

Ashland

Serene mountain escape with poolside relaxation and hiking trails for outdoor adventures.

$62 nightly

$69 total

Nov 1 - Nov 2

Total with taxes and fees

A poolside area with lounge chairs and umbrellas.

A hotel lobby with a wooden reception desk, a large chandelier, and a compass-themed floor design.

A spacious indoor seating area with blue sofas and round tables, large windows with a view of the beach and umbrellas, and a flat-screen TV mounted on the wall.

A deck with outdoor seating, a bar area, and a fire feature.

6. Compass by Margaritaville in Medford

Medford

Splash into sun-soaked serenity at this Medford retreat with poolside cabanas and cocktail service.

$155 nightly

$173 total

Oct 26 - Oct 27

Total with taxes and fees

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

A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

A kitchen with a countertop displaying various food items, a refrigerator, and a coffee machine.

A hotel lobby with a reception desk, blue upholstered sofas, a patterned carpet, and a decorative wall.

7. Comfort Inn & Suites Ashland

Ashland

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

$112 nightly

$114 total

Nov 15 - Nov 16

Total with taxes and fees

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

A well-maintained garden with a paved walkway, surrounded by lush greenery and trees.

A well-lit room with a sofa, chairs, and a coffee table. There are bookshelves filled with books and decorative items.

A bar area with a marble countertop, wine bottles, and glasses. There are hanging pendant lights and a 'No Minors' sign.

8. Lithia Springs Resort

Ashland

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

$110 nightly

$112 total

Nov 8 - Nov 9

Total with taxes and fees

View all properties

Choose what matters most at hotels with a pool in Ashland

Breakfast included

Hot tub

Spa

4 stars

5 stars

Hotels with pools and free breakfast in Ashland

A breakfast buffet area with labeled food stations, including hot food, cereal, and fruit.

A multi-story building with a modern architectural design, featuring a mix of balconies and windows.

A hotel room with a blue sofa, a black coffee table, a bed with white linens, and a large window with curtains.

A modern hotel room with a dark wood wardrobe, a black refrigerator, a microwave, a sink, and a chair.

Holiday Inn Express & Suites Ashland by IHG

Ashland

$96 nightly

$107 total

Nov 16 - Nov 17

Total with taxes and fees

A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

A hotel lobby with a reception desk, blue upholstered sofas, a patterned carpet, and a decorative wall.

A hotel room with a gray sofa, a small wooden table, a framed picture on the wall, a floor lamp, and a carpeted floor.

A hotel room with a bed, a desk with a TV, a chair, and a microwave.

Comfort Inn & Suites Ashland

Ashland

$112 nightly

$114 total

Nov 15 - Nov 16

Total with taxes and fees

Exterior

A restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.

A patio with stone flooring, wooden chairs, and a wooden fence in the background.

A hotel room with a large bed, a separate sitting area, a large bathtub, and a flat-screen TV.

Best Western Windsor Inn

Ashland

$106 nightly

$118 total

Oct 31 - Nov 1

Total with taxes and fees

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

An outdoor patio with a fire pit, seating, and potted plants.

A lobby with leather sofas, a rug, and lamps.

A restaurant with wooden chairs and tables, large windows, and a dragon sculpture.

Stratford Inn

Siskiyou-Hargadine Historic District

$86 nightly

$96 total

Nov 4 - Nov 5

Total with taxes and fees

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

A room with four armchairs, a bench, and a table with a lamp. There are large windows with a view of greenery outside.

A restaurant with multiple tables and booths, large windows with a view of trees, and hanging decorative light fixtures.

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

Historic Downtown District

$119 nightly

$133 total

Nov 4 - Nov 5

Total with taxes and fees

A sign for Prospero's Flagship Inn with a star emblem and a pedestrian crossing sign nearby.

A wooden deck with white lounge chairs and a table, surrounded by a wooden fence and trees.

A hotel entrance with a sign, a pedestrian crossing sign, and a road with trees.

A hotel room with a large bed, two bedside tables with lamps, a wooden headboard, a framed picture on the wall, a mirror above the sink, and striped carpeting.

Prospero's Flagship Inn

Ashland

$56 nightly

$62 total

Oct 26 - Oct 27

Total with taxes and fees

A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

A garden with a pond, stone walls, and various plants.

A sunlit room with large windows, a dining table, chairs, and a sofa.

A gazebo with a wooden roof and white curtains, surrounded by lush greenery and autumn-colored trees.

Country Willows Inn and Estate

Ashland

$215 nightly

$219 total

Nov 1 - Nov 2

Total with taxes and fees

View all properties

Hotels with pools and hot tubs in Ashland

A breakfast buffet area with labeled food stations, including hot food, cereal, and fruit.

A multi-story building with a modern architectural design, featuring a mix of balconies and windows.

A hotel room with a blue sofa, a black coffee table, a bed with white linens, and a large window with curtains.

A modern hotel room with a dark wood wardrobe, a black refrigerator, a microwave, a sink, and a chair.

Holiday Inn Express & Suites Ashland by IHG

Ashland

$96 nightly

$107 total

Nov 16 - Nov 17

Total with taxes and fees

A hotel entrance with outdoor seating, potted plants, and a well-lit facade.

A hotel lobby with a reception desk, blue upholstered sofas, a patterned carpet, and a decorative wall.

A hotel room with a gray sofa, a small wooden table, a framed picture on the wall, a floor lamp, and a carpeted floor.

A hotel room with a bed, a desk with a TV, a chair, and a microwave.

Comfort Inn & Suites Ashland

Ashland

$112 nightly

$114 total

Nov 15 - Nov 16

Total with taxes and fees

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

An outdoor patio with a fire pit, seating, and potted plants.

A lobby with leather sofas, a rug, and lamps.

A restaurant with wooden chairs and tables, large windows, and a dragon sculpture.

Stratford Inn

Siskiyou-Hargadine Historic District

$86 nightly

$96 total

Nov 4 - Nov 5

Total with taxes and fees

Exterior

A restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.

A patio with stone flooring, wooden chairs, and a wooden fence in the background.

A hotel room with a large bed, a separate sitting area, a large bathtub, and a flat-screen TV.

Best Western Windsor Inn

Ashland

$106 nightly

$118 total

Oct 31 - Nov 1

Total with taxes and fees

A resort with a covered walkway, potted plants, and a statue.

A well-maintained garden with a paved walkway, surrounded by lush greenery and trees.

A well-lit room with a sofa, chairs, and a coffee table. There are bookshelves filled with books and decorative items.

A bar area with a marble countertop, wine bottles, and glasses. There are hanging pendant lights and a 'No Minors' sign.

Lithia Springs Resort

Ashland

$110 nightly

$112 total

Nov 8 - Nov 9

Total with taxes and fees

A spacious lobby with a large wooden floor, a green peace sign decoration, and a large window offering a view of the outdoors.

A spacious living room with a high ceiling, large windows, and a mix of seating arrangements including a sofa and chairs.

A bar area with a high ceiling, a TV mounted on the wall, and a bar counter with various bottles.

A hotel with a swimming pool, multiple balconies, and a view of the surrounding landscape.

Ashland Hills Hotel & Suites

Ashland

$121 nightly

$135 total

Nov 4 - Nov 5

Total with taxes and fees

A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

A garden with a pond, stone walls, and various plants.

A sunlit room with large windows, a dining table, chairs, and a sofa.

A gazebo with a wooden roof and white curtains, surrounded by lush greenery and autumn-colored trees.

Country Willows Inn and Estate

Ashland

$215 nightly

$219 total

Nov 1 - Nov 2

Total with taxes and fees

A hallway with a blue wall, a framed welcome sign, a round mirror, and a table.

A spacious living room with a fireplace, a dining area, and a view through large windows.

A modern bedroom with a large bed, a bench, a wardrobe, and a ceiling fan.

A two-story house with a front porch, a blue door, and a well-maintained garden with various shrubs and a small tree.

The Ashland Social | Main House

Ashland

$603 nightly

$672 total

Oct 19 - Oct 20

Total with taxes and fees

A two-story house with a blue front door, number 485, surrounded by well-maintained lawns and flowering trees.

A modern bedroom with a large bed, a bench, a wardrobe, and a ceiling fan.

A spacious living room with a fireplace, a dining area, and a view through large windows.

A modern kitchen with wooden cabinets, a central island, stainless steel appliances, and pendant lighting.

The Ashland Social | Entire Estate

Ashland

$712 nightly

$794 total

Oct 19 - Oct 20

Total with taxes and fees

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

Prospero's Flagship Inn

Prospero's Flagship Inn

8/10 Good

"Would love to have the hard boiled eggs back for protein! Easier access to regular coffee pods for in room"

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent

"The gnome is game is so fun. Wish the pool was inside but overall loved everything"

Best Western Windsor Inn

Best Western Windsor Inn

8/10 Good

"Breakfast was nearly empty and not great- staff did not care. Older property, it was reasonably clean but out of date."

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

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

8/10 Good

"The room was clean and the bed was comfortable. However, the pillows are in dire need for an upgrade. And the bathroom could use a renovation. The hotel is very convenient for attending the theater at the Shakespeare Festival, and is also a short walk to all of the area restaurants. In addition, it was very convenient to have two free, electric car chargers in the parking lot."

Ashland Motel - Oregon

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."

Timbers INN and Suites

Timbers INN and Suites

10/10 Excellent

"Our room was very clean and comfortable and our staff interaction was great. We’ll definitely stay here again when we come to Ashland."

Baymont by Wyndham

Baymont by Wyndham

8/10 Good

"It was quiet, clean and reasonably priced. The wi fi worked well in the room"

Frequently asked questions

How much does a hotel with outdoor pool in Ashland cost?

Enjoy staying in a hotel in Ashland with an outdoor pool. You can find a great deal from $62 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

What are some of the best Ashland hotels with outdoor pools and scenic views?

The Arden Forest Inn is a delightful 4-star retreat that boasts a stunning outdoor pool set against breathtaking mountain views. Guests rave about the comfortable and clean rooms, as well as the convenient parking options. With a remarkable traveller rating of 9.8, this hotel ensures a serene escape while being close to exciting skiing activities nearby.Another excellent choice is the Stratford Inn, which has a friendly setting complemented by its outdoor pool and picturesque surroundings. Rated 9.4 by visitors, the Stratford Inn is praised for its friendly and helpful staff, spacious and clean rooms, and a great location that makes it easy to explore the area. Guests also appreciate the delicious breakfast options available during their stay.For those seeking good value, the Best Western Windsor Inn is a fantastic option with a rating of 9.0. This hotel features an outdoor pool and provides free breakfast and Wi-Fi, ensuring a comfortable and convenient stay. Guests frequently highlight the friendly staff and well-kept rooms, making it a top pick for travellers.Lastly, The Bard's Inn, part of the BW Signature Collection by Best Western, brings a cozy ambiance with its outdoor pool and lovely mountain views. With a traveller rating of 8.6, visitors enjoy the great location and comfortable rooms, along with a complimentary breakfast that exceeds expectations.

Are there hotels in Ashland with outdoor pool activities or events?

Ashland, Oregon, is a delightful destination known for its vibrant arts scene and stunning natural beauty. Travellers often flock to this charming town not just for its world-class theaters, like the Oregon Shakespeare Festival, but also for its welcoming accommodations that enhance their stay. For those seeking a refreshing outdoor experience, there are several hotels with outdoor pool activities and events.One standout option is the Ashland Hills Hotel and Suites, which features a seasonal outdoor pool and a relaxing hot tub. Guests can unwind poolside while enjoying convenient food and drink service from the on-site Luna Cafe. The family-friendly atmosphere and organized activities around the pool make it a great choice for those traveling with children or looking to socialize.Another excellent choice is Lithia Springs Resort, which boasts a beautifully designed outdoor saline swimming pool, also seasonal, along with a hot tub. The resort's picnic areas and fire pits provide a cozy setting for evenings, and guests can opt for spa packages that enhance their relaxation experience.For a unique twist, the Jackson WellSprings, located just outside of Ashland, offers a large natural hot springs pool filled with mineral water. This serene environment is great for wellness activities and workshops, making it an ideal retreat for those looking to rejuvenate and connect with nature.

Is it cheaper to book flights and a Ashland hotel with a pool as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Ashland for you.

Explore a world of travel with Expedia

Ashland Vacation Rentals