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Holiday Rentals in Ashland

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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 €243
includes taxes & fees
18 Oct - 19 Oct
Barclay Klum House by WanderLodges
A house with a wooden deck, a stone wall, and a wooden fence.

2. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (240 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is €261
includes taxes & fees
18 Oct - 19 Oct
The Ashland Cottage, walk to town
A deck with a fire pit, outdoor seating, and a view of the countryside.

3. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is €366
includes taxes & fees
15 Oct - 16 Oct
Grandview of Ashland
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

4. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Excellent stay. Very responsive host. Would come back"
United States
Scott N.
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.

5. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (5 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 €193
includes taxes & fees
18 Oct - 19 Oct
Hanna's House by WanderLodges
A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

6. 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.
East Main Downtown Bungalow
A hotel room with a large bed, two wall-mounted lamps, a chandelier, a window with curtains, and a small table with a chair.

7. 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 Matriarch| Suite 3 | Pet friendly
A bedroom with a bed, bedside tables, a wardrobe, a chair, and a window.

8. 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, (59 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.
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
A large, dark-colored building with a symmetrical facade, multiple windows, and a central entrance with a covered walkway.

9. Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (22 reviews)
"Just a little cleaner exterior"
United States
David
Chateau Herbe ~ Oberon Suite w/ Kitchen
A house with a covered porch, outdoor seating, and a staircase leading to the entrance.

10. 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 €255
includes taxes & fees
1 Nov - 2 Nov
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
A modern kitchen with wooden beams, a dining area with a rug, and a large island.

11. 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 €344
includes taxes & fees
18 Oct - 19 Oct
The Mountain Ave House by WanderLodges
A modern kitchen with white cabinets, a refrigerator, stove, and microwave. There is a dining area with a glass table and brown chairs.

12. 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.
Charming carriage house in Ashland near downtown
A residential property with a gated entrance, a wooden deck, and a well-maintained hedge.

13. 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 Ashland Social | Guest Studio
A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

14. 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 €376
includes taxes & fees
25 Oct - 26 Oct
Savage Upon Siskiyou
A porch with wicker furniture, a small table, and a plaid rug.

15. 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 €154
includes taxes & fees
1 Nov - 2 Nov
Affordable Luxury- One block to Downtown
A covered outdoor area with a stone pathway, a wooden railing, and a green chair.

16. Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (17 reviews)
"Perfect spot to walk to the shows at OSF, walk Lithia Park, and eat and shop at all the downtown spots. Comfortable bed, quiet place, we will try to book this again for our next OSF trip!"
United States
Lara G.
The price is €205
includes taxes & fees
18 Oct - 19 Oct
Quaint Downtown Ashland Studio- pet friendly!
A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

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

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
10.0 out of 10, Exceptional, (171 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
Hanna`s House | Downtown Retreat, Steps to OSF
A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

18. Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Ashland
10.0 out of 10, Exceptional, (6 reviews)
"Lovely stay in a nicely restored historic home. We were very comfortable and the location is great in central Ashland."
United States
Casey K.
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Terrace/patio

19. Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.

Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (12 reviews)
"Close to town, very nice room. We had fun in Ashland."
United States
Adam B.
Relax in the luxurious 1-bedroom Louisa Suite at RedTail Inn. Enjoy a double rain shower, plush linens, and a shared hot tub. Located near downtown Ashland, with off-street parking and high-speed WiFi.
A kitchen with a stainless steel sink, white cabinets, and a flat-screen TV mounted above the cabinets.

20. Swank Suites | King with Lux Tub

Swank Suites | King with Lux Tub
Historic Railroad District
9.4 out of 10, Exceptional, (3 reviews)
"This is definitely the place we will hope to stay next time! Great location, sweet cottage, and easy everything."
United States
Bridget A.
Swank Suites | King with Lux Tub
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

Relax Inn At Ashland

Relax Inn At Ashland

8/10 Good
"Great little room that was very clean and had access to a coffee stand, gas station, and several spots for food. The hotel had friendly staff, decent parking, and affordable prices. It was perfect for a stay to visit Ashland, Medford, and Crater Lake. Overall a great stay."
Sean 3-night trip
Posted 14 hours ago
Relax Inn At Ashland

Find out more about Ashland

Everything you need to know about Ashland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland holiday rentals we have selected for you start as low as €154 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.