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Ashland Holiday Rentals

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Ashland holiday rentals

Smart TV

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (51 reviews)
"Len provided me with an outdoor table and extra chairs so I could have dinner outside with my family because one had the flu. So wonderful to be able to socialize with everyone without risking getting the flu! House was very comfortable and well supplied. Close to downtown and hiking. Off street parking for one car. Thank you so much!!!"
United States
Judy
The price is HK$870
HK$1,800 total
includes taxes & fees
26 Aug - 27 Aug
East Main Downtown Bungalow
Interior detail

Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is HK$1,334
HK$2,090 total
includes taxes & fees
10 Aug - 11 Aug
Hanna's House by WanderLodges
Smart TV, books

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (67 reviews)
"Spacious, clean studio to explore Ashland!"
United States
Suzanne
Courtside Cottage - WalkScore 93 - Dog Friendly
Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is HK$1,796
HK$3,305 total
includes taxes & fees
10 Aug - 11 Aug
Savage Upon Siskiyou
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (53 reviews)
"The Carriage House was amazing! Better than anticipated. Super close to downtown, beautifully appointed, and priced really well! We only stayed one night while driving from California to northern Oregon but we wished we had planned our trip so we could have stayed longer. We will definitely be back. I highly recommend staying here."
United States
Teresa
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
2 bedrooms, laptop workspace, iron/ironing board, free WiFi

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is HK$1,263
HK$2,414 total
includes taxes & fees
30 Jul - 31 Jul
Barclay Klum House by WanderLodges
Terrace/patio

Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (16 reviews)
"Excellent communication as I asked if we could check in early as I arrived earlier than expected. Room was quiet and comfortable. Understood the street parking so was expecting it. Centrally located to downtown. No issues. Thanks for the stay."
United States
Ralph
Quaint Downtown Ashland Studio- pet friendly!
Exterior

Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (18 reviews)
"very relaxing in a beautiful environment with easy access to the OSF and restaurants "
United States
Larry D.
The price is HK$1,427
HK$1,990 total
includes taxes & fees
27 Aug - 28 Aug
Chateau Herbe ~ Oberon Suite w/ Kitchen
Smart TV, books, music library, stereo

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Ashland
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is HK$1,059
HK$1,902 total
includes taxes & fees
26 Aug - 27 Aug
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Exterior detail

The Ashland Social | Guest Studio

The Ashland Social | Guest Studio
Ashland
10.0 out of 10, Exceptional, (27 reviews)
"Our out of town in-laws loved their stay. We highly recommend it!"
United States
Alessandro C.
The price is HK$847
HK$1,876 total
includes taxes & fees
12 Aug - 13 Aug
The Ashland Social | Guest Studio
Terrace/patio

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.6 out of 10, Exceptional, (48 reviews)
"Fantastic location, wonderful amenities. Would absolutely stay here again!!"
United States
Daniel
The price is HK$1,357
HK$1,950 total
includes taxes & fees
17 Aug - 18 Aug
A Cowslip's Belle Inn
Dining

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
Living area

The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is HK$1,874
HK$3,226 total
includes taxes & fees
16 Aug - 17 Aug
The Mountain Ave House by WanderLodges
Terrace/patio

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)
"Well stocked and comfortable, we didn’t have time for the hot tub, but the shower was lovely."
United States
ashley 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.
Smart TV

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, (170 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.
The price is HK$1,285
HK$2,375 total
includes taxes & fees
10 Aug - 11 Aug
Hanna`s House | Downtown Retreat, Steps to OSF
Sun deck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Grandview of Ashland was a beautiful home!! It was super clean and the views of the valley were amazing. Our entire party had a wonderful time and would 100% stay there again. Highly recommend!"
United States
Paul
The price is HK$2,110
HK$3,726 total
includes taxes & fees
16 Aug - 17 Aug
Grandview of Ashland
Exterior

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (8 reviews)
"Loved loved loved staying here and had a fantastic stay with very reasonable rates! It is a bit difficult to find where the apartment was, but once we figured that part out, everything fell right into place. Huge thank you to the hosts for their excellent and timely communication- I also was a huge fan of the easy check in and check out process. Views are spectacular in this area and make for a really special and beautiful stay."
United States
Cameron A.
The price is HK$1,560
HK$2,140 total
includes taxes & fees
2 Aug - 3 Aug
Chateau Herb ~ Miranda Carriage House Apt
Terrace/patio

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$1,716
HK$2,739 total
includes taxes & fees
26 Aug - 27 Aug
The Peerless Hotel | Signature ADA Room #1 | Artist`s Abode | Historic District
Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (231 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is HK$1,380
HK$2,334 total
includes taxes & fees
17 Aug - 18 Aug
The Ashland Cottage, walk to town
Iron/ironing board, travel cot, WiFi, bed sheets

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.
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

Callahan's Mountain Lodge

Callahan's Mountain Lodge

8/10 Good
"There was no complimentary breakfast"
Philippa 1-night trip
Posted 7 hours ago
Callahan's Mountain Lodge

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
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  • 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?

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly: This highly rated holiday home rental in Ashland offers a patio, a garden and a BBQ 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. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate Gorgeous Lakeside BarnHOUSE + SAUNA! as a favourite home for rent in Ashland.

How many holiday rentals are there in Ashland?

Choose from 105 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Angus Bowmer Theatre and Oregon Shakespeare Festival, whereas Lithia Park and North Mountain Park are a couple of picturesque spots to enjoy the outdoors. Emigrant Lake and Mount Ashland Ski Area 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.