Ashland Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Ashland holiday rentals

Terrace/patio

A Cowslip's Belle Inn

A Cowslip's Belle Inn
3.0 star property
Ashland
9.8 out of 10, Exceptional, (41 reviews)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is HK$789
HK$1,315 total
includes taxes & fees
28 Jan - 29 Jan
A Cowslip's Belle Inn
Living area

Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is HK$933
HK$2,075 total
includes taxes & fees
1 Feb - 2 Feb
Barclay Klum House by WanderLodges
Sun deck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (3 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$1,677
HK$3,119 total
includes taxes & fees
28 Jan - 29 Jan
Grandview of Ashland
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.
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Exterior detail

Cozy Ashland Studio: King Bed, 1 mile from Plaza!

Cozy Ashland Studio: King Bed, 1 mile from Plaza!
Ashland
10.0 out of 10, Exceptional, (25 reviews)
"Just what was advertised. Cozy."
United States
Weston C.
The price is HK$624
HK$1,568 total
includes taxes & fees
1 Feb - 2 Feb
Cozy Ashland Studio: King Bed, 1 mile from Plaza!
Smart TV, books

Railroad District, steps to downtown, everything you need to enjoy Ashland!

Railroad District, steps to downtown, everything you need to enjoy Ashland!
Historic Railroad District
The price is HK$2,105
HK$4,425 total
includes taxes & fees
28 Jan - 29 Jan
Railroad District, steps to downtown, everything you need to enjoy Ashland!
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)
"This place was a 10/10! Made a big breakfast for my friends. Grocery store very close. I will be returning!"
United States
Montgomery
The price is HK$1,627
HK$3,023 total
includes taxes & fees
1 Feb - 2 Feb
The Mountain Ave House by WanderLodges
Terrace/patio

Quaint Downtown Ashland Studio- pet friendly!

Quaint Downtown Ashland Studio- pet friendly!
Ashland
9.2 out of 10, Wonderful, (13 reviews)
"Cute little place in a great location close to downtown Ashland theatre district. We were able to walk everywhere. Very communicative hosts. "
United States
Chris H.
The price is HK$663
HK$1,622 total
includes taxes & fees
28 Jan - 29 Jan
Quaint Downtown Ashland Studio- pet friendly!
Smart TV, books

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (60 reviews)
"Very clean, great location. Well appointed . Loved it and would definitely come back. "
United States
Dawn
The price is HK$697
HK$1,612 total
includes taxes & fees
28 Jan - 29 Jan
Courtside Cottage - WalkScore 93 - Dog Friendly
Exterior

Hobart Peak Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Hobart Peak Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland
10.0 out of 10, Exceptional, (1 review)
"This place exceeded expectations. Very clean, well maintained, and well built cabin with a loft and jacuzzi tub. The restaurant was closed, but the Hyatt was 8 minutes away, and was told by the helpful person there that the restaurant will open again soon. Will definitely look to book another say during winter."
United States
Ryan G.
The price is HK$1,123
HK$2,833 total
includes taxes & fees
28 Jan - 29 Jan
Hobart Peak Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Fireplace

Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland
10.0 out of 10, Exceptional, (3 reviews)
"We had a great two-night stay. Beautiful home. No hair dryer, which was listed as an amenity, was a not so happy surprise."
United States
Vicki W.
The price is HK$1,123
HK$2,184 total
includes taxes & fees
29 Jan - 30 Jan
Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Exterior

Homey Rustic Cabin in the Cascades

Homey Rustic Cabin in the Cascades
Jackson County
10.0 out of 10, Exceptional, (1 review)
"Great location cabin was perfect for a group large upstairs sleeping areas. Outside was great "
United Kingdom
Troy K.
The price is HK$1,246
HK$2,744 total
includes taxes & fees
28 Jan - 29 Jan
Homey Rustic Cabin in the Cascades
Property grounds

The Red Dragon House

The Red Dragon House
Ashland
10.0 out of 10, Exceptional, (105 reviews)
"House was definitely pet friendly. Dogs always enjoy staying there. Very relaxing place. Beds are comfortable. House is always clean excellent place to stay"
United States
karen
The price is HK$1,396
HK$1,575 total
includes taxes & fees
30 Jan - 31 Jan
The Red Dragon House
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, (38 reviews)
"The place was very clean and comfortable. Would recommend it and will stay there again."
United States
Ellen H.
The price is HK$772
HK$1,469 total
includes taxes & fees
1 Feb - 2 Feb
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (212 reviews)
"Perfect Stay!"
United States
Anonymous traveller
The price is HK$1,302
HK$2,217 total
includes taxes & fees
28 Jan - 29 Jan
The Ashland Cottage, walk to town
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$807
HK$1,499 total
includes taxes & fees
4 Feb - 5 Feb
Hanna's House by WanderLodges
4 bedrooms, desk, iron/ironing board, travel cot

Luxury Ashland Mountain Escape: Pool, Hot Tub

Luxury Ashland Mountain Escape: Pool, Hot Tub
Ashland
9.4 out of 10, Exceptional, (3 reviews)
"This property was wonderful for our family of 5 teens. The kitchen was well stocked, beds comfortable and it also had a nice quiet and calm feel. Can't wait to come back. "
United States
siobhan c.
Luxury Ashland Mountain Escape: Pool, Hot Tub
Smart TV

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, (3 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.
The price is HK$986
HK$2,332 total
includes taxes & fees
28 Jan - 29 Jan
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Exterior

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay, with full kitchen, and a close drive to downtown Ashland. The AC stopped and the staff were very responsive and provided."
United States
Catherine J.
The price is HK$1,186
HK$1,702 total
includes taxes & fees
28 Jan - 29 Jan
Chateau Herb ~ Miranda Carriage House Apt
Terrace/patio

Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44

Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
Jackson County
10.0 out of 10, Exceptional, (4 reviews)
"One night stay, very peaceful "
United Kingdom
Joshua S.
The price is HK$1,246
HK$2,338 total
includes taxes & fees
28 Jan - 29 Jan
Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"Great hotel I highly recommend 😊"
Conrad 1-night trip
Posted 7 hours ago
Ashland Hills Hotel & Suites

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. Some other homes for rent in Ashland include Chateau Herb ~ Miranda Carriage House Apt and The Red Dragon House.

How many holiday rentals are there in Ashland?

Choose from 103 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Oregon Shakespeare Festival, whereas Lithia Park and Howard Prairie Lake are a couple of picturesque spots to enjoy the outdoors. Oregon Cabaret Theatre 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.