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Ashland Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Ashland holiday rentals

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

1. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is HK$925
HK$2,037 total
includes taxes & fees
29 Oct - 30 Oct
Barclay Klum House by WanderLodges
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

2. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Very easy and convenient stay. Walking distance to park and downtown. Cute studio."
United States
opticnirvana
The price is HK$1,305
HK$2,382 total
includes taxes & fees
24 Nov - 25 Nov
Courtside Cottage - WalkScore 93 - Dog Friendly
A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

3. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is HK$883
HK$1,588 total
includes taxes & fees
2 Nov - 3 Nov
Hanna's House by WanderLodges
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

4. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is HK$1,404
HK$2,703 total
includes taxes & fees
1 Nov - 2 Nov
The Mountain Ave House by WanderLodges
A house with a wooden deck, a stone wall, and a wooden fence.

5. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is HK$1,310
HK$2,239 total
includes taxes & fees
1 Nov - 2 Nov
The Ashland Cottage, walk to town
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

6. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is HK$1,255
HK$2,703 total
includes taxes & fees
22 Nov - 23 Nov
Savage Upon Siskiyou
A deck with a fire pit, outdoor seating, and a view of the countryside.

7. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
The price is HK$1,433
HK$3,039 total
includes taxes & fees
1 Nov - 2 Nov
Grandview of Ashland
A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

8. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is HK$946
HK$1,781 total
includes taxes & fees
29 Oct - 30 Oct
Charming carriage house in Ashland near downtown
A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

9. The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
9.8 out of 10, Exceptional, (29 reviews)
"A great place to call home while you're away from home."
United States
Tara M.
The price is HK$706
HK$1,704 total
includes taxes & fees
29 Oct - 30 Oct
The Ashland Social | Guest Studio
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

10. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (55 reviews)
"The bungalow was great. Every room was comfortable and efficient for what we needed. The location is perfect...quiet yet easy walk to anywhere downtown. We would stay here again!!"
United States
Amy R.
The price is HK$734
HK$1,667 total
includes taxes & fees
1 Nov - 2 Nov
East Main Downtown Bungalow
A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

11. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.6 out of 10, Exceptional, (24 reviews)
"Just a little cleaner exterior"
United States
David
The price is HK$1,193
HK$1,737 total
includes taxes & fees
29 Oct - 30 Oct
Chateau Herbe ~ Oberon Suite w/ Kitchen
A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

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

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (62 reviews)
"This is an excellent place to stay. It is well equipped with everything you might need for your stay. And the location is perfect."
United States
Karen G.
The price is HK$926
HK$1,662 total
includes taxes & fees
11 Nov - 12 Nov
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
A two-story house with a porch, a wooden fence, and a paved driveway.

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

Downtown Ashland Studio - 3 blocks from the plaza!
Ashland
9.2 out of 10, Wonderful, (24 reviews)
"This was a great little place in a great location. The host was very responsive, really easy to work with and made our stay easy. We highly recommend!"
United States
Santiago L.
The price is HK$745
HK$1,758 total
includes taxes & fees
29 Oct - 30 Oct
Downtown Ashland Studio - 3 blocks from the plaza!
A living room with a green sofa, a television, a wooden coffee table, and a patterned rug.

14. The Matriarch| Suite 3 | Pet friendly

The Matriarch| Suite 3 | Pet friendly
Historic Railroad District
9.6 out of 10, Exceptional, (8 reviews)
"We stayed one night and walked easily to a show in one of the Shakespeare theatres. The apartment was super-comfortable and excellent in every way! Highly recommended!"
United States
Daniel
The price is HK$1,145
HK$1,452 total
includes taxes & fees
1 Nov - 2 Nov
The Matriarch| Suite 3 | Pet friendly
A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

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

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Historic Downtown District
9.8 out of 10, Exceptional, (137 reviews)
"Room was in fantastic shape, clean, well decorated, close to everything. As an Air B&B owner, I recommend, if staying Ashland stay here. Great host."
United States
James C.
The price is HK$988
HK$2,038 total
includes taxes & fees
1 Nov - 2 Nov
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
A porch with wicker furniture, a small table, and a plaid rug.

16. Affordable Luxury- One block to Downtown

Affordable Luxury- One block to Downtown
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Perfect location- We typically visit twice a year and like to stay in railroad district as it is close to restaurants and OSF. Highly recommend Swank House."
United States
Sue K.
The price is HK$1,004
HK$1,295 total
includes taxes & fees
29 Oct - 30 Oct
Affordable Luxury- One block to Downtown
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

The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic District
Historic Railroad District
The price is HK$768
HK$1,493 total
includes taxes & fees
1 Nov - 2 Nov
The Peerless Hotel | Signature Room #6 | Clawfoot Tub |Historic 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

The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Historic Railroad District
10.0 out of 10, Exceptional, (1 review)
"The sights stunning, the garden a delight & the jacuzzi soak enriched my soul & ailing body"
United States
David B.
The price is HK$854
HK$1,593 total
includes taxes & fees
2 Nov - 3 Nov
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Comfortable wicker seating to enjoy your morning coffee or evening wine.

19. Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!

Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
Siskiyou-Hargadine Historic District
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location and had all the touches to make it a comfortable stay"
United States
Sara C.
The price is HK$1,079
HK$2,057 total
includes taxes & fees
31 Oct - 1 Nov
Charming 1 BR Orliena Suite in historic downtown Ashland, OR. Walk to the Oregon Shakespeare Festival, shops, and dining. Features a kitchenette, plush queen bed, and shared hot tub access. Dog friendly!
A modern bedroom with a large bed, wooden slatted ceiling, a flat-screen TV, and a built-in wardrobe.

20. Swank House -Downtown Suite- Pet Friendly

Swank House -Downtown Suite- Pet Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (7 reviews)
"Welcoming, cute and private outdoor patio. Cozy but spacious bed and room. Pet-Friendly. Would definitely stay again."
United States
Katie I.
The price is HK$973
HK$1,289 total
includes taxes & fees
2 Nov - 3 Nov
Swank House -Downtown Suite- Pet Friendly
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 Ashland Hotel Reviews

Prospero's Flagship Inn

Prospero's Flagship Inn

10/10 Excellent
"For a quick stop in Ashland this place was ideal for me - clean, very comfortable, safe, inexpensive, and convenient. 5 minutes off the highway, and a family Mexican restaurant and a coffee shop next door. What’s not to like?"
Scott 1-night trip
Posted less than an hour ago
Prospero's Flagship Inn

Find out more about Ashland

Search for holiday rentals in Ashland on Expedia! You can easily find your home rentals, villas, holiday apartments in Ashland using one of the methods below:

  • View our selection of featured holiday rentals in Ashland
  • Use the map to find apartments and other holiday homes in the Ashland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ashland while they last

Look no further and take a look at our great range of rental properties in Ashland!

Frequently asked questions

Can I find holiday rentals in Ashland?

Yes, there are holiday rentals in Ashland close to ScienceWorks Hands-On Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theatre 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 holiday rentals that Ashland has to offer?

Premier Downstairs Flat in Perfect Down Town Location : This highly rated holiday home rental in Ashland is located in the city centre, 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 that 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 holiday rentals are there in Ashland?

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

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 holiday rentals like in Ashland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Ashland. Holiday rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family getaway.