Hotels with a Pool in Ashland

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Nov 7 - Nov 8
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Nov 13 - Nov 15
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Nov 20 - Nov 22

Hotels with a Pool in Ashland

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

1. Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
  • Indoor pool
  • Pool loungers
  • Hot tub
9.4 out of 10, Exceptional, (1,795 reviews)
Splash into the warm indoor pool and children's wading area, then soak in the hot tub after exploring nearby hiking trails. Mountain vistas frame this pet-friendly haven with spacious rooms and outdoor gathering spaces.
The price is $102
$114 total
includes taxes & fees
Nov 8 - Nov 9
Stratford Inn
An indoor swimming pool with multiple lanes, a changing room, and a sauna area.

2. Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
2.5 star property
Ashland
  • Indoor pool
  • Hot tub
9.2 out of 10, Wonderful, (1,005 reviews)
Swimming enthusiasts cherish the indoor pool, available from 7 AM to 10 PM daily, while the adjacent hot tub melts away travel tension. After aquatic adventures, guests retreat to immaculately clean rooms, consistently praised for their comfortable bedding and modern amenities.
The price is $92
$103 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express & Suites Ashland by IHG
A resort with a covered walkway, potted plants, and a statue.

3. Lithia Springs Resort

Lithia Springs Resort
3.0 star property
Ashland
  • Outdoor pool
  • Pool loungers
  • Hot tub
9.4 out of 10, Exceptional, (1,010 reviews)
Mineral-infused waters invite relaxation at both the sun-drenched outdoor pool and therapeutic hot tub. After enjoying garden strolls, guests appreciate luxurious spa treatments, wine tastings in the dedicated room, and continental breakfast praised for its excellent variety.
The price is $94
$115 total
includes taxes & fees
Nov 16 - Nov 17
Lithia Springs Resort
A swimming pool with orange and white lounge chairs, surrounded by a fence and trees.

4. Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
3.0 star property
Ashland
  • Outdoor pool
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (1,577 reviews)
Sparkling waters invite relaxation at the outdoor pool complete with sun loungers and a soothing hot tub. Active guests enjoy 2 tennis courts, complimentary bicycles, and a fitness center, all within this mountain-view sanctuary.
The price is $106
$128 total
includes taxes & fees
Nov 23 - Nov 24
Ashland Hills Hotel & Suites
An indoor swimming pool with a clear view of the pool area, a staircase, and seating arrangements.

5. Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
2.5 star property
Ashland
  • Indoor pool
  • Pool loungers
  • Hot tub
9.0 out of 10, Wonderful, (1,068 reviews)
Soak tired muscles in the pristine indoor swimming pool, available around the clock alongside a rejuvenating hot tub. Sun loungers invite lazy afternoons, while pet owners appreciate the reasonable fees and ample walking space.
The price is $97
$98 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Ashland
A pool area with lounge chairs and a hot tub, surrounded by a building with a balcony and stairs.

6. Best Western Windsor Inn

Best Western Windsor Inn
2.5 star property
Ashland
  • Outdoor pool
  • Hot tub
9.0 out of 10, Wonderful, (1,001 reviews)
Refreshing waters await at this immaculately clean hotel's seasonal outdoor pool, open May through October. Guests love unwinding in the hot tub after exploring nearby Southern Oregon University and ScienceWorks Museum.
The price is $113
$125 total
includes taxes & fees
Nov 14 - Nov 15
Best Western Windsor Inn
A pool area with lounge chairs and a covered seating area.

7. 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
  • Pool loungers
8.4 out of 10, Very good, (1,004 reviews)
Swimming becomes an event at this tranquil pool retreat, complete with inviting sun loungers for post-Shakespeare Festival relaxation. Minutes from downtown Asheville and Lithia Park, guests appreciate the hot tub and clean, comfortable accommodations.
The price is $95
$106 total
includes taxes & fees
Nov 24 - Nov 25
The Bard's Inn, BW Signature Collection by Best Western
A poolside area with lounge chairs and umbrellas, a pool, and a view of trees and mountains.

8. Prospero's Flagship Inn

Prospero's Flagship Inn
2.5 star property
Ashland
  • Pool
  • Free breakfast
  • Free parking
  • Free WiFi
  • Restaurant
  • Connecting rooms available
8.4 out of 10, Very good, (1,490 reviews)
Sparkling waters await at the seasonal outdoor pool, open April through October with extended 8:00 AM to 8:00 PM hours. Nearby mountain biking trails and the hotel's garden create a refreshing retreat in the heart of Ashland.
The price is $71
$79 total
includes taxes & fees
Nov 8 - Nov 9
Prospero's Flagship Inn
A swimming pool with a wooden deck, a lifebuoy, and white plastic chairs.

9. Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
2.0 star property
Ashland
  • Outdoor pool
  • Indoor pool
  • Pool loungers
7.4 out of 10, Good, (1,000 reviews)
Splash between seasons in the indoor and outdoor pools at this tranquil Ashland hotel. After swimming, rejuvenate in the sauna or steam room before exploring nearby hiking trails, skiing, and hot springs.
The price is $75
$84 total
includes taxes & fees
Nov 8 - Nov 9
Cedarwood Inn of Ashland
A swimming pool with a clear view of the poolside area, including lounge chairs and a covered seating area.

10. Timbers INN and Suites

Timbers INN and Suites
2.0 star property
Ashland
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
8.8 out of 10, Excellent, (1,004 reviews)
Poolside paradise awaits with a seasonal outdoor swimming spot open June through September. Friendly staff and spotlessly clean rooms earn rave reviews, while nearby mountain biking trails promise active adventures beyond the water.
The price is $68
$76 total
includes taxes & fees
Nov 20 - Nov 21
Timbers INN and Suites
A clear swimming pool with a wooden fence, surrounded by lounge chairs.

11. Ashland Motel - Oregon

Ashland Motel - Oregon
2.0 star property
Ashland
  • Pool
  • Free WiFi
  • Air conditioning
  • Non-smoking
8.0 out of 10, Very good, (251 reviews)
Splash into vacation mode at the pristine seasonal outdoor pool, open June through September. Mountain biking trails, lush gardens, and immaculate rooms create the perfect basecamp for exploring North Mountain Park and Ashland's treasures.
The price is $79
$88 total
includes taxes & fees
Nov 8 - Nov 9
Ashland Motel - Oregon
A swimming pool at night with lounge chairs and a warning sign about no lifeguard on duty.

12. Arden Forest Inn

Arden Forest Inn
4.0 star property
Ashland
  • Pool loungers
9.8 out of 10, Exceptional, (115 reviews)
Sunbathe in style at the seasonal outdoor pool, a peaceful oasis surrounded by Victorian charm and lush gardens. Cross-country skiing and snowboarding options nearby complement this upscale retreat with its welcoming terrace and library.
The price is $152
$169 total
includes taxes & fees
Nov 8 - Nov 9
Arden Forest Inn
A backyard with a swimming pool, patio furniture, a small pond, and a wooden cabin.

13. Country Willows Inn and Estate

Country Willows Inn and Estate
4.0 star property
Ashland
  • Pool loungers
9.8 out of 10, Exceptional, (45 reviews)
Poolside relaxation defines summer stays at this upscale rural retreat, where guests over 10 can enjoy swimming surrounded by acclaimed gardens. Impeccable breakfasts and friendly staff complete the experience in this intimate getaway.
The price is $215
$219 total
includes taxes & fees
Nov 8 - Nov 9
Country Willows Inn and Estate
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

14. Palm Cottages

Palm Cottages
2.5 star property
Ashland
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
  • Electric vehicle charging point
9.2 out of 10, Wonderful, (233 reviews)
Dive into the refreshing seasonal outdoor pool, open May to October with ideal water temperatures and comfortable lounging areas. Palm Cottages offers premium bedding, iPads in every room, and sits conveniently near Southern Oregon University and Lithia Park.
The price is $239
$266 total
includes taxes & fees
Nov 8 - Nov 9
Palm Cottages
An indoor swimming pool with clear water, a lifeguard chair, and exit signs.

15. Holiday Inn Express & Suites Medford by IHG

Holiday Inn Express & Suites Medford by IHG
2.5 star property
Medford
  • Indoor pool
9.2 out of 10, Wonderful, (1,000 reviews)
Splash into vacation mode at the clean, family-friendly indoor pool where relaxation reigns supreme. Located near the airport with complimentary shuttle service, this hotel offers comfortable rooms and a fitness center for active travelers.
The price is $103
$116 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Medford by IHG
A hotel with a swimming pool, sun loungers, and umbrellas.

16. Compass by Margaritaville in Medford

Compass by Margaritaville in Medford
4.0 star property
Medford
  • Outdoor pool
  • Poolside bar
  • Pool loungers
9.6 out of 10, Exceptional, (1,202 reviews)
Poolside bliss beckons with private cabanas, sun loungers, and a lively bar serving cold drinks. Beyond aquatic fun, guests enjoy an adjacent golf course, hiking trails, and fire pits for evening relaxation after swimming.
The price is $152
$183 total
includes taxes & fees
Nov 8 - Nov 9
Compass by Margaritaville in Medford
A spa area with a hot tub, seating, and large windows offering views of buildings and a distant landscape.

17. Hilton Garden Inn Medford, OR 

Hilton Garden Inn Medford, OR 
3.0 star property
Medford
  • Indoor pool
8.8 out of 10, Excellent, (1,001 reviews)
The price is $86
$97 total
includes taxes & fees
Dec 6 - Dec 7
Hilton Garden Inn Medford, OR 
An indoor swimming pool with clear blue water, surrounded by white chairs and a tiled wall.

18. Comfort Inn South

Comfort Inn South
2.5 star property
Medford
  • Indoor pool
  • Hot tub
8.8 out of 10, Excellent, (1,002 reviews)
Sparkling indoor pool and rejuvenating hot tub create a wellness haven year-round. Guests rave about peaceful atmosphere, spotless facilities, and the delicious complimentary breakfast featuring homemade waffles and omelets.
The price is $76
$85 total
includes taxes & fees
Nov 29 - Nov 30
Comfort Inn South
An indoor swimming pool with a clear water surface, a diving board, and several lounge chairs along the poolside.

19. Homewood Suites Medford

Homewood Suites Medford
3.0 star property
Medford
  • Indoor pool
8.8 out of 10, Excellent, (1,001 reviews)
The price is $89
$101 total
includes taxes & fees
Nov 29 - Nov 30
Homewood Suites Medford
A hot tub area with a tiled floor, a metal ladder, and a pool.

20. Clarion Pointe Medford

Clarion Pointe Medford
2.5 star property
Medford
  • Indoor pool
  • Hot tub
8.0 out of 10, Very good, (1,079 reviews)
Sparkling clean waters invite swimmers to unwind at the immaculate indoor pool open from 6:00 AM to 10:00 PM daily. Adjacent hot tub bubbles with perfect temperature, creating an ideal retreat after workouts in the 24-hour fitness center.
The price is $81
$91 total
includes taxes & fees
Nov 26 - Nov 27
Clarion Pointe Medford
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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Discover your perfect hotel with a pool in Ashland

Breakfast included
Hot tub

Hotels with pools and free breakfast in Ashland

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

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1795)
The price is $102
$114 total
includes taxes & fees
Nov 8 - Nov 9
Stratford Inn
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Hotels with pools and hot tubs in Ashland

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

Stratford Inn

Stratford Inn
2.5 star property
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (1795)
The price is $102
$114 total
includes taxes & fees
Nov 8 - Nov 9
Stratford 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.
View all properties

Top neighborhoods in Ashland

A rusted metal bridge in a forested area.

Historic Railroad District

Ashland's Historic Railroad District captures Oregon's cultural heart with Victorian charm and artistic soul. Tree-lined streets connect 19th-century buildings where theater and history share the spotlight. The Shakespeare Festival brings brick walkways alive with theatrical buzz. Art galleries in former rail buildings showcase local talent amid cobblestone plazas adorned with bronze sculptures. Farm-to-table restaurants serve Pacific Northwest cuisine in converted Victorian spaces, perfect for dining with regional wines. Boutique inns and historic bed & breakfasts offer intimate stays with period furnishings and modern comforts. The pedestrian-friendly design makes exploring a joy, with attractions within an easy stroll through this walkable cultural haven.

A town with buildings and trees in autumn colors, surrounded by mountains.

Skidmore Academy Historic District

Step back in time as you stroll the tree-lined streets of Skidmore Academy Historic District, where Victorian architecture meets theatrical flair. Ornate 19th-century buildings, including the original Skidmore Academy, tell the story of Ashland's rich heritage. The district sits conveniently close to Oregon Shakespeare Festival venues, where world-class performances bring creative energy to this peaceful neighborhood. Intimate cafes and bistros cater to theater-goers with pre-show dining featuring seasonal Pacific Northwest ingredients. Charming bed-and-breakfasts in converted Victorian homes offer cozy accommodations with period furnishings. The walkable streets connect easily to downtown Ashland, making exploration a breeze without the need for public transportation.

A paved pedestrian area with trees, a white building with a green awning, and a dog walking.
Photo by Shannon Willitts
Open Photo by Shannon Willitts

Historic Downtown District

Historic Downtown District brings Shakespeare to life in Ashland's charming center. The renowned Oregon Shakespeare Festival anchors the neighborhood with Tudor-style theaters surrounded by Victorian storefronts. Lithia Park offers a peaceful escape with bubbling mineral springs, while art galleries and boutiques fill historic buildings beneath colorful awnings. Farm-to-table restaurants showcase local Oregon wines, though reservations are essential during festival season. Accommodation options include Victorian bed & breakfasts and boutique inns within this highly walkable neighborhood. Most attractions sit within a three-block radius, making cars unnecessary for exploring this theatrical paradise.

A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

Siskiyou-Hargadine Historic District offers a step back in time with pristine Victorian and Craftsman homes lining tree-canopied streets. Take a leisurely stroll through architectural history while enjoying the peaceful vibe just steps from Ashland's cultural buzz. The Oregon Shakespeare Festival and Oregon Cabaret Theatre are an easy walk away, making this neighborhood perfect for theater enthusiasts. Accommodations range from charming bed & breakfasts in restored Victorians to boutique inns with period furnishings. Downtown Ashland's diverse restaurants and artisan shops are just a 5-10 minute walk away. The neighborhood's uncrowded sidewalks and proximity to Lithia Park create an ideal base for exploring Ashland without a car.

Top landmarks in Ashland

A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.
Photo by Patrick Glassford
Open Photo by Patrick Glassford

Oregon Shakespeare Festival

9.2/10 (620 reviews)
If you want to see a show while you're in town, try and grab some tickets at Oregon Shakespeare Festival in Historic Downtown District. If you enjoy the show and want to see another, Allen Elizabethan Theatre, Oregon Cabaret Theatre, and Thomas Theatre are all a short walk away.
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About the destination

Visitors to Ashland like this welcoming city's gardens, entertainment, restaurants, and festivals. Activities like hiking give you a chance to enjoy the outdoors while you're in town. Nature lovers can visit Lithia Park and Emigrant Lake. There's plenty more to see, including sights like Allen Elizabethan Theatre and Angus Bowmer Theatre.