Hotels in Ashland

October 2026
November 2026

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Where to stay in Ashland?

1. Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
Ashland
$118
$142 total
includes taxes & fees
Oct 19 - Oct 20
Ashland Hills Hotel & Suites

2. Prospero's Flagship Inn

Prospero's Flagship Inn
Ashland
$72
$80 total
includes taxes & fees
Sep 29 - Sep 30
Prospero's Flagship Inn

3. Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District
$94
$105 total
includes taxes & fees
Oct 13 - Oct 14
Stratford Inn

4. Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
Ashland
$179
$200 total
includes taxes & fees
Sep 27 - Sep 28
Plaza Inn & Suites at Ashland Creek

5. Compass by Margaritaville in Medford

Compass by Margaritaville in Medford
Medford
$152
$183 total
includes taxes & fees
Oct 12 - Oct 13
Compass by Margaritaville in Medford

6. Lithia Springs Resort

Lithia Springs Resort
Ashland
$137
$159 total
includes taxes & fees
Oct 27 - Oct 28
Lithia Springs Resort

7. Best Western Windsor Inn

Best Western Windsor Inn
Ashland
$113
$125 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Windsor Inn

8. Ashland Springs Hotel

Ashland Springs Hotel
Historic Downtown District
$145
$178 total
includes taxes & fees
Oct 27 - Oct 28
Ashland Springs Hotel

9. Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland
$113
$114 total
includes taxes & fees
Oct 5 - Oct 6
Comfort Inn & Suites Ashland

10. Red Lion Hotel Rogue Regency Medford Airport

Red Lion Hotel Rogue Regency Medford Airport
Medford
$93
$110 total
includes taxes & fees
Sep 29 - Sep 30
Red Lion Hotel Rogue Regency Medford Airport

11. 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
Sep 27 - Sep 28
The Bard's Inn, BW Signature Collection by Best Western

12. Winchester Inn

Winchester Inn
Historic Downtown District
$175
$213 total
includes taxes & fees
Oct 26 - Oct 27
Winchester Inn

13. Palm Cottages

Palm Cottages
Ashland
$201
$224 total
includes taxes & fees
Sep 27 - Sep 28
Palm Cottages

14. McCall House Boutique Inn

McCall House Boutique Inn
Historic Downtown District
$306
$341 total
includes taxes & fees
Oct 5 - Oct 6
McCall House Boutique Inn

15. Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
Ashland
$92
$103 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Express & Suites Ashland by IHG

16. Arden Forest Inn

Arden Forest Inn
Ashland
$180
$201 total
includes taxes & fees
Oct 4 - Oct 5
Arden Forest Inn

17. Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn
Skidmore Academy Historic District
$260
$290 total
includes taxes & fees
Oct 27 - Oct 28
Abigail’s Bed & Breakfast Inn

18. Country Willows Inn and Estate

Country Willows Inn and Estate
Ashland
$282
$286 total
includes taxes & fees
Sep 27 - Sep 28
Country Willows Inn and Estate

19. The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
Historic Railroad District
$167
$241 total
includes taxes & fees
Sep 28 - Sep 29
The Peerless Hotel by WanderLodges

20. Executive Residency by Best Western Medford

Executive Residency by Best Western Medford
Medford
$84
$95 total
includes taxes & fees
Oct 4 - Oct 5
Executive Residency by Best Western Medford
View all properties

Check out pet-friendly hotels in Ashland

Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District
$94
$105 total
includes taxes & fees
Oct 13 - Oct 14
Stratford Inn

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
Ashland
$118
$142 total
includes taxes & fees
Oct 19 - Oct 20
Ashland Hills Hotel & Suites

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland
$113
$114 total
includes taxes & fees
Oct 5 - Oct 6
Comfort Inn & Suites Ashland

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
Ashland
$92
$103 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Express & Suites Ashland by IHG

Best Western Windsor Inn

Best Western Windsor Inn
Ashland
$113
$125 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Windsor Inn

Ashland Springs Hotel

Ashland Springs Hotel
Historic Downtown District
$145
$178 total
includes taxes & fees
Oct 27 - Oct 28
Ashland Springs Hotel

Callahan's Mountain Lodge

Callahan's Mountain Lodge
Ashland
$134
$151 total
includes taxes & fees
Oct 5 - Oct 6
Callahan's Mountain Lodge

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek
Ashland
$179
$200 total
includes taxes & fees
Sep 27 - Sep 28
Plaza Inn & Suites at Ashland Creek

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
Sep 27 - Sep 28
The Bard's Inn, BW Signature Collection by Best Western

Relax Inn At Ashland

Relax Inn At Ashland
Ashland
$78
$87 total
includes taxes & fees
Oct 4 - Oct 5
Relax Inn At Ashland
View all properties

You may also like hotels with hot tubs in Ashland

Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District
$94
$105 total
includes taxes & fees
Oct 13 - Oct 14
Stratford Inn

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
Ashland
$118
$142 total
includes taxes & fees
Oct 19 - Oct 20
Ashland Hills Hotel & Suites

Lithia Springs Resort

Lithia Springs Resort
Ashland
$137
$159 total
includes taxes & fees
Oct 27 - Oct 28
Lithia Springs Resort

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
Ashland
$92
$103 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Express & Suites Ashland by IHG

Best Western Windsor Inn

Best Western Windsor Inn
Ashland
$113
$125 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Windsor Inn

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland
$113
$114 total
includes taxes & fees
Oct 5 - Oct 6
Comfort Inn & Suites Ashland

Ashland Springs Hotel

Ashland Springs Hotel
Historic Downtown District
$145
$178 total
includes taxes & fees
Oct 27 - Oct 28
Ashland Springs Hotel

Callahan's Mountain Lodge

Callahan's Mountain Lodge
Ashland
$134
$151 total
includes taxes & fees
Oct 5 - Oct 6
Callahan's Mountain Lodge

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges
Historic Railroad District
$167
$241 total
includes taxes & fees
Sep 28 - Sep 29
The Peerless Hotel by WanderLodges

Green Springs Inn

Green Springs Inn
Ashland
$82
$108 total
includes taxes & fees
Sep 29 - Sep 30
Green Springs Inn
View all properties

You can also stay at hotels with a pool in Ashland

Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District
$94
$105 total
includes taxes & fees
Oct 13 - Oct 14
Stratford Inn

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
Ashland
$118
$142 total
includes taxes & fees
Oct 19 - Oct 20
Ashland Hills Hotel & Suites

Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG
Ashland
$92
$103 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Express & Suites Ashland by IHG

Best Western Windsor Inn

Best Western Windsor Inn
Ashland
$113
$125 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Windsor Inn

Prospero's Flagship Inn

Prospero's Flagship Inn
Ashland
$72
$80 total
includes taxes & fees
Sep 29 - Sep 30
Prospero's Flagship Inn

Lithia Springs Resort

Lithia Springs Resort
Ashland
$137
$159 total
includes taxes & fees
Oct 27 - Oct 28
Lithia Springs Resort

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland
$113
$114 total
includes taxes & fees
Oct 5 - Oct 6
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
Sep 27 - Sep 28
The Bard's Inn, BW Signature Collection by Best Western

Cedarwood Inn of Ashland

Cedarwood Inn of Ashland
Ashland
$97
$108 total
includes taxes & fees
Sep 27 - Sep 28
Cedarwood Inn of Ashland

Ashland Motel - Oregon

Ashland Motel - Oregon
Ashland
$86
$96 total
includes taxes & fees
Sep 27 - Sep 28
Ashland Motel - Oregon
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Go beyond your typical stay in Ashland

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Pet friendly
Pet friendly
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Pool
Pool
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Hot tub
Hot tub
spa image
Spa
Spa
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Family friendly
Family friendly
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Resort
Resort
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Cabin
Cabin
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Apart­ment
Apart­ment
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Cottage
Cottage
Our prices for hotels in Ashland are cheapest in February

Price trends for hotels in Ashland

Pricing is based on two traveler single night rates
View properties in September

September

High 26°C / low 9°C. Sunny most days.
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Monthly weather averages (˚C)

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 wood duck standing on rocks with moss and greenery in the background.

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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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, Allen Elizabethan Theatre, and Thomas Theatre are all a short walk away.
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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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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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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, Oregon Shakespeare Festival, Oregon Cabaret Theatre, and Angus Bowmer Theatre are all a short walk away.
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Angus Bowmer Theatre

10.0/10 (11 reviews)
If you want to see a show while you're in town, try and grab some tickets at Angus Bowmer Theatre in Historic Downtown District. If you enjoy the show and want to see another, Allen Elizabethan Theatre, Oregon Shakespeare Festival, and Oregon Cabaret Theatre are all a short walk away.
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Learn more about Ashland

Between Shakespeare and the sublime, this artsy enclave captivates with its cultural punch far beyond its size. The Oregon Shakespeare Festival transforms three theaters into worlds of drama nearly year-round, drawing theater lovers who linger after standing ovations. Main Street's independent boutiques and farm-to-table restaurants showcase local creativity without pretension. Lithia Park unfolds like a living painting—creek-side paths wind through 93 acres where picnickers claim spots beneath ancient trees. Southern Oregon University adds youthful energy to this intellectual haven. After hiking nearby trails, soak tired muscles in Lithia Plaza's mineral-rich fountains (warning: the water tastes terrible). For a perfect day, catch a matinee, browse gallery-quality crafts, then toast the sunset with local wines.

See all hotels in Ashland
A stone bridge over a calm stream with autumn leaves.

Check out reviews of Ashland hotels guests love

Winchester Inn

Winchester Inn
Historic Downtown District

10/10 Exceptional

United States
Anonymous traveler
Winchester Inn

Palm Cottages

Palm Cottages
Ashland

10/10 Exceptional

United States
James
Palm Cottages

Abigail’s Bed & Breakfast Inn

Abigail’s Bed & Breakfast Inn
Skidmore Academy Historic District

10/10 Exceptional

United States
Anonymous traveler
Abigail’s Bed & Breakfast Inn

Best Western Windsor Inn

Best Western Windsor Inn
Ashland

10/10 Exceptional

United States
BRENT
Best Western Windsor Inn

Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland
Ashland

10/10 Exceptional

United States
Barry
Comfort Inn & Suites Ashland

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites
Ashland

10/10 Exceptional

United States
Melissa
Ashland Hills Hotel & Suites

Magnolia Hotel

Magnolia Hotel
Jacksonville Historic District

10/10 Exceptional

United States
brian
Magnolia Hotel

Callahan's Mountain Lodge

Callahan's Mountain Lodge
Ashland

10/10 Exceptional

United States
Vera
Callahan's Mountain Lodge

The City Center Motel

The City Center Motel
City Center Medford

10/10 Exceptional

United States
Anonymous traveler
The City Center Motel

Hilton Garden Inn Medford, OR 

Hilton Garden Inn Medford, OR 
Medford

10/10 Exceptional

United States
Sarah
Hilton Garden Inn Medford, OR 

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

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

10/10 Exceptional

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

Prospero's Flagship Inn

Prospero's Flagship Inn
Ashland

10/10 Exceptional

United States
johnny
Prospero's Flagship Inn

Ashland Motel - Oregon

Ashland Motel - Oregon
Ashland

10/10 Exceptional

United States
Anonymous traveler
Ashland Motel - Oregon

Grandview of Ashland

Grandview of Ashland
Ashland

10/10 Exceptional

United States
Jose
Grandview of Ashland

Hanna's House by WanderLodges

Hanna's House by WanderLodges
Historic Railroad District

10/10 Exceptional

United States
David
Hanna's House by WanderLodges

Country Willows Inn and Estate

Country Willows Inn and Estate
Ashland

10/10 Exceptional

United States
Forrest
Country Willows Inn and Estate

Arden Forest Inn

Arden Forest Inn
Ashland

10/10 Exceptional

United States
catherine
Arden Forest Inn

Stratford Inn

Stratford Inn
Siskiyou-Hargadine Historic District

10/10 Exceptional

United States
Adrianna
Stratford Inn

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
Ashland

10/10 Exceptional

United States
Carmen
Barclay Klum House by WanderLodges

Lithia Springs Resort

Lithia Springs Resort
Ashland

10/10 Exceptional

United States
Angelika
Lithia Springs Resort