Ashland Vacation Rentals from AED 314: Search Short-Term Rentals

A stone bridge over a calm stream with autumn leaves.

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Our top choices for Ashland vacation rentals

A garden with a stone pathway, various plants, a barbecue grill, and a bicycle.

1. Whimsy on B

Historic Railroad District

AED 584 total

includes taxes & fees

14 Nov - 15 Nov

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

2. Barclay Klum House by WanderLodges

Ashland

Melissa

AED 944 total

includes taxes & fees

13 Dec - 14 Dec

A wooden door with a small window above it, a porch with a wooden railing, and a green hose on the right side.

3. Whimsy On B 2br & Studio

Historic Railroad District

AED 1,172 total

includes taxes & fees

16 Nov - 17 Nov

A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

4. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

AED 1,245 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

5. Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District

Andrea R.

AED 922 total

includes taxes & fees

1 Dec - 2 Dec

A deck with a fire pit, outdoor seating, and a view of the countryside.

6. Grandview of Ashland

Ashland

Jose

AED 1,342 total

includes taxes & fees

2 Dec - 3 Dec

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

7. Hanna's House by WanderLodges

Historic Railroad District

Robert

AED 657 total

includes taxes & fees

18 Nov - 19 Nov

A house with a wooden deck, a stone wall, and a wooden fence.

8. The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District

Julie S.

AED 1,048 total

includes taxes & fees

14 Nov - 15 Nov

A two-story house with a porch, a wooden fence, and a paved driveway.

9. Downtown Ashland Studio - 3 blocks from the plaza!

Ashland

Santiago L.

A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

10. Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Siskiyou-Hargadine Historic District

Karen G.

AED 677 total

includes taxes & fees

16 Nov - 17 Nov

A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

11. Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Historic Downtown District

Elaine H.

AED 954 total

includes taxes & fees

13 Nov - 14 Nov

A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

12. The Ashland Social | Guest Studio

Ashland

Tara M.

A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

13. Charming carriage house in Ashland near downtown

Skidmore Academy Historic District

Cyndy K.

AED 761 total

includes taxes & fees

18 Nov - 19 Nov

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

14. The Mountain Ave House by WanderLodges

Ashland

Joyce

AED 1,104 total

includes taxes & fees

13 Dec - 14 Dec

A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

15. East Main Downtown Bungalow

Historic Railroad District

Melissa D.

AED 768 total

includes taxes & fees

17 Nov - 18 Nov

A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

16. Hanna`s House | Downtown Retreat, Steps to OSF

Historic Railroad District

Jim L.

AED 815 total

includes taxes & fees

13 Dec - 14 Dec

A two-story wooden house with a fenced backyard, outdoor seating, and a statue.

17. The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District

Historic Railroad District

A two-story building with a balcony, a patio with white chairs, and a statue.

18. The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

Historic Railroad District

David B.

A porch with wicker furniture, a small table, and a plaid rug.

19. Affordable Luxury- One block to Downtown

Historic Railroad District

Sue K.

AED 582 total

includes taxes & fees

15 Nov - 16 Nov

A living room with a green sofa, a television, a wooden coffee table, and a patterned rug.

20. The Matriarch| Suite 3 | Pet friendly

Historic Railroad District

Daniel

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Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Barclay Klum House by WanderLodges

Ashland

10/10 Excellent

sharon

Grandview of Ashland

Ashland

10/10 Excellent

Sonja

Hanna's House by WanderLodges

Historic Railroad District

10/10 Excellent

Robert

The Mountain Ave House by WanderLodges

Ashland

10/10 Excellent

Mary

A red brick building with a balcony and a covered entrance.

Lady Geneva Bed and Breakfast

City Center Medford

10/10 Excellent

Anonymous traveler

A garden pathway with wisteria and red flowers, surrounded by lush greenery.

Arden Forest Inn

Ashland

10/10 Excellent

catherine

A spacious kitchen with a central island, bar stools, and a fireplace.

Paschal Winery

Talent

10/10 Excellent

I loved the isolated RV with a gorgeous view of the pond and the swans were absolutely gorgeous. The rv was in great condition and very comfortable. My only suggestions would be to leave stove directions and label the knobs better. My mother in law struggled turning it on and off. We also had an alarm sound during the night a couple of times and it wasnt related to the gas. Maybe humidity? A towel for the bathroom floor would have been useful and less throw pillows to find homes for. But...

Lisa

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

Winchester Inn

Historic Downtown District

10/10 Excellent

This hotel is comprised of two Victorian style houses. One is just rooms and the other is the restaurant/bar with rooms too (I think). The gardens were gorgeous, the staff was super friendly and here was the clincher...they could feed my wife despite several food allergies. We were so floored when we came down to breakfast and they had made my wife a special pastry and seamlessly provided her second course. The rooms are in keeping with the style of the property. If you want sleek...

Anonymous traveler

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

The Peerless Hotel by WanderLodges

Historic Railroad District

10/10 Excellent

Amber

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

McCall House Boutique Inn

Historic Downtown District

10/10 Excellent

Pamela

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

Siskiyou-Hargadine Historic District

10/10 Excellent

We had a great stay. The location is perfect. It’s close to everything and there is a grocery store right across the street which was very convenient. The pool was awesome. It was the warmest hotel pool I’ve ever swam in. Continental breakfast was really good. They have a cold breakfast which includes a yogurt bar with two different yogurt options and lots a different toppings to choose from. They also had toast, bagels, muffins, cereal, coffee, tea, juice and more.

Adrianna

An outdoor seating area with wicker furniture, a stone wall, and a fire feature.

Fairfield Inn & Suites by Marriott Medford

Medford

10/10 Excellent

HACKED

A modern two-story house with a wooden exterior and stone accents, surrounded by landscaped gardens with various plants and a flagpole.

Resort at Eagle Point

Eagle Point

10/10 Excellent

Anonymous traveler

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

Lithia Springs Resort

Ashland

10/10 Excellent

Angelika

A modern hotel lobby with multiple seating areas, including round tables and chairs, and a bar area with stools.

Springhill Suites By Marriott Medford Airport

Medford

10/10 Excellent

Theresa

A large, white, multi-story house with a stone foundation, multiple chimneys, and a well-maintained lawn.

Hummingbird Estate Wine & Suites

Central Point

10/10 Excellent

I can highly recommend Hummingbird!!! My recent stay was excellent, on every level! The property is gorgeous, the suites are clean, modernized but still have been decorated to go with their signature style, the service was impeccable and the breakfasts were delicious! Every morning something new, fresh, and a culinary delight! Thank you so all at Hummingbird for a wonderful stay! I was staying as a solo for this trip, but would love to return again with my Hubby! I would absolutely stay again...

Anonymous traveler

An outdoor patio with seating under a pergola, string lights, and a fire pit.

Magnolia Hotel

Jacksonville Historic District

10/10 Excellent

brian

A balcony with a view of a residential area, a black pickup truck, and a white RV parked in the foreground.

Ashland Commons Hostel

Ashland

10/10 Excellent

Brenda

Frequently Asked Questions

Can I find vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theater scene this destination is known for. Leave some time to check out the lively festivals and top-notch restaurants during your visit.

What are some of the best vacation rentals that Ashland has to offer?

Premier Downstairs Flat in Perfect Down Town Location : This highly rated vacation home rental in Ashland is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Ashland include Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly and Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. .

How many vacation rentals are there in Ashland?

Choose from 106 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Shakespeare Festival and Oregon Cabaret Theatre are other places to visit while you're in town.

What are vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.

Ashland Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland vacation rentals

1. Whimsy on B

2. Barclay Klum House by WanderLodges

3. Whimsy On B 2br & Studio

4. Savage Upon Siskiyou

5. Courtside Cottage - WalkScore 93 - Dog Friendly

6. Grandview of Ashland

7. Hanna's House by WanderLodges

8. The Ashland Cottage, walk to town

9. Downtown Ashland Studio - 3 blocks from the plaza!

10. Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

11. Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

12. The Ashland Social | Guest Studio

13. Charming carriage house in Ashland near downtown

14. The Mountain Ave House by WanderLodges

15. East Main Downtown Bungalow

16. Hanna`s House | Downtown Retreat, Steps to OSF

17. The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District

18. The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District

19. Affordable Luxury- One block to Downtown

20. The Matriarch| Suite 3 | Pet friendly

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Barclay Klum House by WanderLodges

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Ashland?

What are some of the best vacation rentals that Ashland has to offer?

How many vacation rentals are there in Ashland?

What can I see and do in Ashland?

What are vacation rentals like in Ashland?