Hotels with a Pool in Ashland

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Tonight
Aug 28 - Aug 29
Tomorrow
Aug 29 - Aug 30
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Top 5 Hotels with a Pool in Ashland at a glance

  1. Holiday Inn Express & Suites Ashland by IHG — 2.5-star hotel in Ashland. Guest rating: 9.2/10 — Wonderful.
  2. Ashland Hills Hotel & Suites — 3-star hotel in Ashland. Guest rating: 8.8/10 — Excellent.
  3. Stratford Inn — 2.5-star hotel in Siskiyou-Hargadine Historic District. Guest rating: 9.4/10 — Exceptional.
  4. Comfort Inn & Suites Ashland — 2.5-star hotel in Ashland. Guest rating: 9.0/10 — Wonderful.
  5. Best Western Windsor Inn — 2.5-star hotel in Ashland. Guest rating: 9.0/10 — Wonderful.

Hotels with a Pool in Ashland

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
Ashland
  • Indoor pool
  • Hot tub
$106
$118 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express & Suites Ashland by IHG

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
Ashland
  • Outdoor pool
  • Pool loungers
  • Hot tub
$115
$138 total
includes taxes & fees
Sep 1 - Sep 2
Ashland Hills Hotel & Suites

Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District
  • Indoor pool
  • Pool loungers
  • Hot tub
$113
$125 total
includes taxes & fees
Aug 31 - Sep 1
Stratford Inn

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland
  • Indoor pool
  • Pool loungers
  • Hot tub
$105
$107 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Ashland

Best Western Windsor Inn

Best Western Windsor Inn
Ashland
  • Outdoor pool
  • Hot tub
$113
$125 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Windsor Inn

Lithia Springs Resort

Lithia Springs Resort
Ashland
  • Outdoor pool
  • Pool loungers
  • Hot tub
$171
$193 total
includes taxes & fees
Sep 7 - Sep 8
Lithia Springs Resort

Prospero's Flagship Inn

Prospero's Flagship Inn
Ashland
  • Pool
  • Free breakfast
  • Free parking
  • Free WiFi
  • Restaurant
  • Connecting rooms available
$89
$99 total
includes taxes & fees
Aug 31 - Sep 1
Prospero's Flagship Inn

Timbers INN and Suites

Timbers INN and Suites
Ashland
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
$85
$95 total
includes taxes & fees
Sep 1 - Sep 2
Timbers INN and Suites

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

The Bard's Inn, BW Signature Collection by Best Western
Historic Downtown District
  • Pool loungers
$169
$188 total
includes taxes & fees
Aug 30 - Aug 31
The Bard's Inn, BW Signature Collection by Best Western

Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
Ashland
  • Outdoor pool
  • Indoor pool
  • Pool loungers
$97
$108 total
includes taxes & fees
Aug 30 - Aug 31
Cedarwood Inn of Ashland

Ashland Motel - Oregon

Ashland Motel - Oregon
Ashland
  • Pool
  • Free WiFi
  • Air conditioning
  • Non-smoking
$92
$103 total
includes taxes & fees
Aug 30 - Aug 31
Ashland Motel - Oregon

Arden Forest Inn

Arden Forest Inn
Ashland
  • Pool loungers
$196
$219 total
includes taxes & fees
Sep 6 - Sep 7
Arden Forest Inn

Palm Cottages

Palm Cottages
Ashland
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
  • Electric vehicle charging point
$201
$224 total
includes taxes & fees
Aug 29 - Aug 30
Palm Cottages

Country Willows Inn and Estate

Country Willows Inn and Estate
Ashland
  • Pool loungers
$282
$286 total
includes taxes & fees
Aug 29 - Aug 30
Country Willows Inn and Estate

Best Western Crater Lake Highway White City/Medford

Best Western Crater Lake Highway White City/Medford
White City
  • Indoor pool
  • Pool loungers
  • Hot tub
$105
$107 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Crater Lake Highway White City/Medford

Fairfield Inn & Suites by Marriott Medford

Fairfield Inn & Suites by Marriott Medford
Medford
  • Indoor pool
$129
$145 total
includes taxes & fees
Sep 6 - Sep 7
Fairfield Inn & Suites by Marriott Medford

Springhill Suites By Marriott Medford Airport

Springhill Suites By Marriott Medford Airport
Medford
  • Indoor pool
$101
$114 total
includes taxes & fees
Sep 7 - Sep 8
Springhill Suites By Marriott Medford Airport

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford
Medford
  • Outdoor pool
  • Poolside bar
  • Pool loungers
$161
$193 total
includes taxes & fees
Sep 6 - Sep 7
Compass by Margaritaville in Medford

Comfort Inn South

Comfort Inn South
Medford
  • Indoor pool
  • Hot tub
$99
$112 total
includes taxes & fees
Sep 27 - Sep 28
Comfort Inn South

Hilton Garden Inn Medford, OR 

Hilton Garden Inn Medford, OR 
Medford
  • Indoor pool
$106
$119 total
includes taxes & fees
Sep 6 - Sep 7
Hilton Garden Inn Medford, OR 
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Discover your perfect hotel with a pool in Ashland

Breakfast included
Hot tub
4 stars
Spa
5 stars

Hotels with pools and free breakfast in Ashland

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
Ashland
$106
$118 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express & Suites Ashland by IHG

Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District
$113
$125 total
includes taxes & fees
Aug 31 - Sep 1
Stratford Inn

Best Western Windsor Inn

Best Western Windsor Inn
Ashland
$113
$125 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Windsor Inn

Prospero's Flagship Inn

Prospero's Flagship Inn
Ashland
$89
$99 total
includes taxes & fees
Aug 31 - Sep 1
Prospero's Flagship Inn

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland
$105
$107 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Ashland

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

The Bard's Inn, BW Signature Collection by Best Western
Historic Downtown District
$169
$188 total
includes taxes & fees
Aug 30 - Aug 31
The Bard's Inn, BW Signature Collection by Best Western

Country Willows Inn and Estate

Country Willows Inn and Estate
Ashland
$282
$286 total
includes taxes & fees
Aug 29 - Aug 30
Country Willows Inn and Estate
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Hotels with pools and hot tubs in Ashland

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
Ashland
$106
$118 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express & Suites Ashland by IHG

Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District
$113
$125 total
includes taxes & fees
Aug 31 - Sep 1
Stratford Inn

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
Ashland
$115
$138 total
includes taxes & fees
Sep 1 - Sep 2
Ashland Hills Hotel & Suites

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland
$105
$107 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Ashland

Lithia Springs Resort

Lithia Springs Resort
Ashland
$171
$193 total
includes taxes & fees
Sep 7 - Sep 8
Lithia Springs Resort

Best Western Windsor Inn

Best Western Windsor Inn
Ashland
$113
$125 total
includes taxes & fees
Sep 7 - Sep 8
Best Western Windsor Inn

Country Willows Inn and Estate

Country Willows Inn and Estate
Ashland
$282
$286 total
includes taxes & fees
Aug 29 - Aug 30
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.
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Top neighborhoods in Ashland

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.

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.

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.

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

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, Angus Bowmer Theatre, Allen Elizabethan Theatre, and Oregon Cabaret Theatre are all a short walk away.
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A pond with ducks, surrounded by trees and a small bridge.
Photo by Shannon Willitts

Lithia Park

9.6/10 (1,250 reviews)
Lithia Park is 0.5 mi (0.9 km) from central Ashland, why not stop by during your stay. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. Want to stretch your legs some more? Head to North Mountain Park, located nearby.
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A snowy forest with tall evergreen trees covered in snow.

Mount Ashland Ski Area

8.6/10 (228 reviews)
Skiers and snowboarders might want to test out the slopes at Mount Ashland Ski Area, a skiing spot located 7.8 mi (12.5 km) from central Ashland.
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Howard Prairie Lake

8.4/10 (33 reviews)
Howard Prairie Lake is 16.1 mi (26 km) from central Ashland, why not stop by during your stay.
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Emigrant Lake

8.4/10 (70 reviews)
Emigrant Lake is 6.3 mi (10.2 km) from central Ashland, why not stop by during your stay. It's also full of great shops and restaurants, so you can spend the afternoon having a wander.
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Allen Elizabethan Theatre

9.4/10 (131 reviews)
If you want to see a show while you're in town, try and grab some tickets at Allen Elizabethan Theatre in Historic Downtown District. If you enjoy the show and want to see another, Thomas Theatre, Oregon Shakespeare Festival, and Oregon Cabaret Theatre are all a short walk away.
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Oregon Cabaret Theatre

9.0/10 (144 reviews)
If you want to see a show while you're in town, try and grab some tickets at Oregon Cabaret Theatre in Historic Downtown District. It's also full of great shops and restaurants, so you can spend the afternoon having a wander. If you enjoy the show and want to see another, Oregon Shakespeare Festival, Thomas Theatre, and Allen Elizabethan Theatre are all a short walk away.
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Ashland Library

8.4/10 (126 reviews)
Ashland Library is worth a pic or two when discovering Siskiyou-Hargadine Historic District.
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