Ashland Holiday Rentals, Oregon: Private House Rentals

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Our top choices for Ashland hotels

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

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

A hotel sign with the name "Straford Inn" and a stone pillar.

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

1. Stratford Inn

Siskiyou-Hargadine Historic District

Jerry W. De

2.444.437 ₫

2.725.547 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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.

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

2. Ashland Hills Hotel & Suites

Ashland

Krishnaharsha

3.363.546 ₫

4.011.224 ₫ total

includes taxes & fees

7 Sept - 8 Sept

An outdoor dining area with a table set for two, surrounded by chairs, a red umbrella, and a stone water feature.

A hotel room with a bed, a sofa, a table with a bottle, glasses, and a fruit basket.

A traditional living room with a fireplace, patterned furniture, and large windows with curtains.

A multi-story hotel with a balcony and outdoor seating area, surrounded by lush greenery and a mountainous backdrop.

3. Plaza Inn & Suites at Ashland Creek

Ashland

Lee

4.203.904 ₫

4.687.353 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

A Holiday Inn Express hotel with a modern design, featuring a prominent entrance and a parking lot.

An indoor swimming pool with clear water, a diving board, and a lifeguard sign.

A hotel lobby with a reception desk, seating area, and a view of the hallway.

4. Holiday Inn Express & Suites Ashland by IHG

Ashland

Hardeep

2.920.288 ₫

3.256.121 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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.

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

5. Comfort Inn & Suites Ashland

Ashland

armida

2.841.746 ₫

2.884.372 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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.

6. Timbers INN and Suites

Ashland

Robin

1.994.661 ₫

2.224.047 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

A two-story house with a porch, a staircase, and a garden.

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

7. Lithia Springs Resort

Ashland

Steven

3.786.239 ₫

4.364.932 ₫ total

includes taxes & fees

5 Oct - 6 Oct

An outdoor patio area with tables and chairs, string lights, and potted plants.

A spacious lobby with a high ceiling, ornate chandelier, and multiple seating areas.

A grand lobby with a high ceiling, large windows, and a central staircase.

A spacious lobby with a grand chandelier, a fireplace, and a large window offering a view of the outdoors.

8. Ashland Springs Hotel

Historic Downtown District

William

4.906.382 ₫

5.889.903 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

9. Best Western Windsor Inn

Ashland

Dennis

2.933.586 ₫

3.270.949 ₫ total

includes taxes & fees

21 Sept - 22 Sept

A cozy room with a wooden bathtub, two armchairs, a TV, and a stone fireplace.

A wooden balcony with a view of a forested area.

An outdoor dining area with round tables, white chairs, and umbrellas.

10. Callahan's Mountain Lodge

Ashland

Michelle

3.170.542 ₫

3.609.525 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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.

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

Historic Downtown District

Dawn

4.149.366 ₫

4.626.542 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

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

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

12. Prospero's Flagship Inn

Ashland

Denise

1.619.195 ₫

1.805.363 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A Victorian-style building with ornate architectural details, large windows, and a red door.

A room with a bay window, two upholstered chairs, a round ottoman, and a small wooden table.

A spacious living room with a large sofa, a dining area with a table and chairs, and a chandelier.

A patio area with string lights, potted plants, and a stone pathway.

13. McCall House Boutique Inn

Historic Downtown District

Elizabeth

7.180.780 ₫

8.006.570 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A dining area with a wooden table and chairs, a potted plant, and a window with blinds.

A home office with a desk, computer, and office chair. There is a brown leather sofa and a patterned rug.

A bedroom with a bed, bedside tables, a nightstand, a dresser, a chair, a rug, and a painting on the wall.

A room with a desk, computer, office chair, and a bookshelf. There are three doors with blinds, a patterned rug, and a potted plant.

14. Cedarwood Inn of Ashland

Ashland

Bradley

2.530.954 ₫

2.822.014 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a covered seating area.

A well-maintained garden with a variety of plants and a wooden fence.

A dining table set with plates, cutlery, and glasses, with two leather stools and a window with blinds in the background.

A compact living space with a kitchenette, a sofa, a coffee maker, and a small refrigerator.

15. Palm Cottages

Ashland

David

5.243.529 ₫

5.846.324 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A two-story building with a wooden facade, large windows, and a front porch with chairs.

A room with a brick wall, wooden floor, green-framed windows, and two upholstered chairs.

A spacious bedroom with a four-poster bed, wooden furniture, and a view of the outdoors.

A room with a brick wall, a wooden dresser, a chair, and a bed.

16. The Peerless Hotel by WanderLodges

Historic Railroad District

JI YUN

3.545.646 ₫

5.379.096 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

17. Country Willows Inn and Estate

Ashland

raymon

6.606.369 ₫

6.705.450 ₫ total

includes taxes & fees

5 Sept - 6 Sept

A large, two-story house with a wrap-around porch and a steeply pitched roof.

A modern living room with a sofa, coffee table, and a TV. There is a large window with curtains, a mirror, and a view of a bedroom.

A bar with multiple shelves of bottles, tables, and chairs arranged for patrons.

A living room with a fireplace, two armchairs, a sofa, and a TV mounted on the wall.

18. Winchester Inn

Historic Downtown District

Albert

4.338.717 ₫

5.292.245 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A hotel room with a desk, laptop, two beds, and a round mirror.

A clear swimming pool with a wooden fence, surrounded by lounge chairs.

A pathway leading to a building with a decorative archway, surrounded by flowering trees and a well-maintained lawn.

A coffee machine with a digital display, a coffee pot, a cup, and a coffee pod.

19. Ashland Motel - Oregon

Ashland

Don

2.052.633 ₫

2.288.685 ₫ total

includes taxes & fees

6 Sept - 7 Sept

A wooden cabin with a deck and stairs, surrounded by trees.

A cabin surrounded by a rock garden and dense forest.

A cozy cabin interior with a wooden table, sofa, and a fireplace.

A spacious living area with large windows, a sofa, a chair, and a wooden floor.

20. Green Springs Inn

Ashland

Taryn

2.134.832 ₫

2.829.015 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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Where to stay in Ashland

Find the best Ashland areas for the activities you enjoy most.

A rusted metal bridge in a forested area.

A wooden railway bridge with graffiti, surrounded by greenery.

A wooden log cabin with two red-framed windows.

The exterior of Ashland Food Cooperative with a sign reading "Do You Have Your Bags Today?" and a dog and bike free zone sign.

Historic Railroad District

Step into Ashland's Historic Railway District where Victorian buildings and artistic energy create a cultural haven. Tree-lined streets lead to the famous Oregon Shakespeare Festival theatres and vibrant art galleries housed in restored 19th-century structures. Cobblestone walkways connect charming plazas adorned with bronze sculptures. The district prioritises pedestrians with limited vehicle access, making exploration a pleasure. Farm-to-table restaurants occupy converted Victorians while cosy cafes offer perfect pre-theater dining spots. Historic bed & breakfasts provide intimate accommodation with period furnishings, completing this arts-focused neighborhood's authentic appeal.

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

A grassy field with trees and a distant view of rolling hills.

Skidmore Academy Historic District

Step back in time to Ashland's Skidmore Academy Historic District, where Victorian-era buildings stand as elegant witnesses to the past. Tree-lined streets lead to ornate homes with wraparound porches and bay windows. The historic academy anchors this charming area, offering a glimpse into 19th-century architectural heritage. This peaceful residential haven sits just steps from the renowned Oregon Shakespeare Festival venues. Theater-goers appreciate the intimate local cafes with seasonal Pacific Northwest cuisine. Visitors can easily explore the district's preserved period homes while enjoying the distinctive atmosphere created by creaking wooden porches and rustling mature trees.

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A paved pedestrian area with trees, a white building with a green awning, and a dog walking.

A building with a purple awning labeled "Caldera Tap House" and a sign with a beer mug illustration.

A historic building with a classical facade, a person standing on the steps, and a wheelchair-accessible sign.

A display window with a large red flower and a sign reading "Oregon Shakespeare Festival Welcome Center".

A building corner with ornate architectural details and arched windows overlooking a cityscape.

Historic Downtown District

Ashland's Historic City centre District combines 19th-century charm with world-class theatre. The Oregon Shakespeare Festival anchors this walkable area where Tudor-style theatres stand alongside Victorian shopfronts and cobblestone plazas. Art galleries, independent bookshops, and farm-to-table restaurants create a culturally rich atmosphere. Lithia Park borders the district with 93 acres of gardens and walking trails. During festival season, the streets buzz with theatergoers and performers. Most attractions sit within a three-block radius, making exploration easy without a car. Mountain views frame this intimate district where history and performing arts thrive together.

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A tree-lined street with a mountain backdrop.

Siskiyou-Hargadine Historic District

The Siskiyou-Hargadine Historic District showcases Ashland's architectural heritage through well-preserved Victorian and Craftsman homes. Tree-canopied streets and manicured gardens create a peaceful residential haven just steps from city centre. Travellers will appreciate the authentic small-town Oregon atmosphere while staying close to cultural attractions. The area sits within walking distance of the renowned Oregon Shakespeare Festival and Lithia Park. Historic bed and breakfasts offer intimate accommodation in restored Victorian homes with period furnishings. Despite its quiet residential character, downtown's diverse dining scene and artisan shops are just a short stroll away.

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Stay near popular Ashland attractions

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.

Oregon Shakespeare Festival

9.2/10 (620 reviews)

At OSF, America's oldest repertory theatre presents Shakespearean classics and bold new works across three venues. Reserve seats for evening performances and arrive early for the free outdoor Green Show entertainment.

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A pond with ducks, surrounded by trees and a small bridge.

Lithia Park

9.6/10 (1,250 reviews)

Stroll through Lithia Park's 93 acres of landscaped beauty alongside Ashland Creek. Discover Japanese gardens, duck ponds, and seasonal foliage while enjoying the serenity of this historic green space.

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A snowy forest with tall evergreen trees covered in snow.

Mount Ashland Ski Area

8.6/10 (228 reviews)

Southern Oregon's premier ski destination offers 44 trails across 240 acres of varied terrain. Enjoy twilight skiing on select evenings for a magical mountain experience under the stars.

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Emigrant Lake

8.4/10 (70 reviews)

Emigrant Lake offers warm waters and scenic views just five miles from Ashland, Oregon. Enjoy the thrilling 280-foot twin flume water slide during summer or camp beneath the stars in this recreational haven.

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Oregon Cabaret Theatre

9.0/10 (144 reviews)

Set in a restored 1911 mission-style church, Oregon Cabaret Theatre pairs professional musical performances with gourmet dining. Enjoy tiered seating with balcony views while savouring chef-prepared meals.

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Howard Prairie Lake

8.4/10 (33 reviews)

A pristine 1,990-acre reservoir in the Cascade Mountains, Howard Prairie Lake offers exceptional trout and bass fishing. Enjoy tranquil boating amid pine forests or unwind at the lakeside resort with mountain views.

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Allen Elizabethan Theatre

9.4/10 (131 reviews)

This open-air Elizabethan-style theatre hosts the renowned Oregon Shakespeare Festival. Evening performances unfold beneath the stars, creating a magical atmosphere reminiscent of Shakespeare's era.

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Angus Bowmer Theatre

10.0/10 (11 reviews)

The heart of Oregon Shakespeare Festival, this intimate 600-seat venue places every audience member within 55 feet of the stage. Experience world-class performances where Shakespeare's words and contemporary works come alive.

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Learn more about Ashland

World-class Shakespeare performances unfold in outdoor theatres surrounded by mountain views from June through October. Lithia Park's trails wind along Ashland Creek, perfect for morning walks before browsing the city centre galleries and craft breweries.

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A stone bridge over a calm stream with autumn leaves.

Top Ashland Hotel Reviews

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

10/10 Excellent

"We appreciated having a charger for our EV. The breakfast was very good and the staff was helpful. The room was clean."

Comfort Inn & Suites Ashland

10/10 Excellent

"Nice big clean room"

Callahan's Mountain Lodge

10/10 Excellent

"If you like the rustic mountain experience, it was excellent. If you expect a lot of staff and extraordinary amenities go somewhere else. Neatness to the Oregon Shakespeare festival and a hot tub in the room an extra special bonus"

Ashland Springs Hotel

10/10 Excellent

"This is well maintained historical property located in the middle of town. It is close to restaurants,shops and theater. It is my favorite place to stay when visiting Ashland."

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"Good breakfast, clean load and friendly staff Will come back for sure"

Lithia Springs Resort

10/10 Excellent

"We had a fabulously relaxing stay."

Timbers INN and Suites

10/10 Excellent

"Older but clean property. Being on special diets, my friend and I both appreciated booking a room with a kitchen (fridge, stove, plates, etc) A bit of a walk to OSF campus for those not used to walking, but doable for younger folks. Does appear to be on the bus line, but we had a car. A few smaller things weren't deal breakers (bigger coffee cups) but we did have major trouble, late at night, with the room key not working. Strongly suggested to mgmt that they replace all door knobs and locks."

Baymont by Wyndham

8/10 Good

"Staff was friendly and the room was clean. AC worked amazing. Would stay again"

Cedarwood Inn of Ashland

8/10 Good

"This is the best place for the right price. Check in is easy. We've stayed twice traveling through. First room was a bit better than the second. Both rooms were good. It's definitely an upgraded old motel but they have added nice modern upgrades. It's quiet too."

More cheap stays in Ashland

Motel 6 Medford, OR - North

2400 Biddle Rd Medford OR

1.329.513 ₫

1.495.604 ₫ total

13 Sept - 14 Sept

includes taxes & fees

Prospero's Flagship Inn

1193 Siskiyou Blvd Ashland OR

1.619.195 ₫

1.805.363 ₫ total

7 Sept - 8 Sept

includes taxes & fees

Ramada by Wyndham Medford Airport North

2111 Biddle Rd Medford OR

1.745.234 ₫

1.963.389 ₫ total

4 Oct - 5 Oct

includes taxes & fees

8.2/10 Very good! (1,082 reviews)

Quality Inn & Suites Medford Airport

1950 Biddle Rd Medford OR

1.901.021 ₫

2.149.343 ₫ total

4 Oct - 5 Oct

includes taxes & fees

Comfort Inn & Suites Ashland

434 S. Valley View Rd. Ashland OR

2.841.746 ₫

2.884.372 ₫ total

28 Sept - 29 Sept

includes taxes & fees

9/10 Wonderful! (1,018 reviews)

Best Western Windsor Inn

2520 Ashland St Ashland OR

2.933.586 ₫

3.270.949 ₫ total

21 Sept - 22 Sept

includes taxes & fees

Hotels in Ashland with star rating

Frequently asked questions

What's the seasonal weather in Ashland?

The hottest months are usually August and July, with an average temperature of 18°C, while the coldest months are December and January, with an average of 3°C. Average annual precipitation for Ashland is 850 mm.

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Book Hotels in Ashland on Expedia.com

Find hotels in Ashland, OR from 1.495.604 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Ashland

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Ashland hotels

1. Stratford Inn

2. Ashland Hills Hotel & Suites

3. Plaza Inn & Suites at Ashland Creek

4. Holiday Inn Express & Suites Ashland by IHG

5. Comfort Inn & Suites Ashland

6. Timbers INN and Suites

7. Lithia Springs Resort

8. Ashland Springs Hotel

9. Best Western Windsor Inn

10. Callahan's Mountain Lodge

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

12. Prospero's Flagship Inn

13. McCall House Boutique Inn

14. Cedarwood Inn of Ashland

15. Palm Cottages

16. The Peerless Hotel by WanderLodges

17. Country Willows Inn and Estate

18. Winchester Inn

19. Ashland Motel - Oregon

20. Green Springs Inn

Where to stay in Ashland

Historic Railroad District

Skidmore Academy Historic District

Historic Downtown District

Siskiyou-Hargadine Historic District

Stay near popular Ashland attractions

Oregon Shakespeare Festival

Lithia Park

Mount Ashland Ski Area

Emigrant Lake

Oregon Cabaret Theatre

Howard Prairie Lake

Allen Elizabethan Theatre

Angus Bowmer Theatre

Learn more about Ashland

Top Ashland Hotel Reviews

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

Comfort Inn & Suites Ashland

Callahan's Mountain Lodge

Ashland Springs Hotel

Plaza Inn & Suites at Ashland Creek

Lithia Springs Resort

Timbers INN and Suites

Baymont by Wyndham

Cedarwood Inn of Ashland

More cheap stays in Ashland

Motel 6 Medford, OR - North

Prospero's Flagship Inn

Ramada by Wyndham Medford Airport North

Quality Inn & Suites Medford Airport

Comfort Inn & Suites Ashland

Best Western Windsor Inn

Hotels in Ashland with star rating

Frequently asked questions

Explore a world of travel with Expedia

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