A resident black-tail deer walks the streets of Ashland, Oregon

Ashland Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Ashland holiday rentals

Sun deck

Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (7 reviews)
"The residence was fantastic in every way. Me and my family enjoyed all the amenities and seeing the wildlife around the house outside. This place is a magical place! Thank you again! We will be back in the near future. "
United States
michael
The price is HK$1,686
HK$3,294 total
includes taxes & fees
25 Jun - 26 Jun
Grandview of Ashland
Outdoor dining

Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Ashland
8.6 out of 10, Excellent, (4 reviews)
"Beautiful spot. Kind host."
United States
Lisa F.
The price is HK$1,523
HK$1,698 total
includes taxes & fees
13 Jun - 14 Jun
Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Outdoor dining

Hot Tub! Peaceful Mountain Cabin at Hyatt Lake

Hot Tub! Peaceful Mountain Cabin at Hyatt Lake
Jackson County
9.4 out of 10, Exceptional, (3 reviews)
"This was our second time staying at this cabin. Once again it was an amazing trip. We really enjoyed our quiet peaceful nights in the hot tub. Celebrated Thanksgiving there it was exactly what we wanted. Can’t wait for our next trip. "
United States
Taryn T.
The price is HK$1,163
HK$2,383 total
includes taxes & fees
15 Jun - 16 Jun
Hot Tub! Peaceful Mountain Cabin at Hyatt Lake
Exterior

Homey Rustic Cabin in the Cascades

Homey Rustic Cabin in the Cascades
Jackson County
10.0 out of 10, Exceptional, (2 reviews)
"Great location cabin was perfect for a group large upstairs sleeping areas. Outside was great "
United Kingdom
Troy K.
The price is HK$1,253
HK$2,797 total
includes taxes & fees
14 Jun - 15 Jun
Homey Rustic Cabin in the Cascades
Fridge, microwave, oven, stovetop

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40
Ashland
9.2 out of 10, Wonderful, (5 reviews)
"It was a nice family kind of place we loved it."
United Kingdom
Nicole F.
The price is HK$1,253
HK$2,491 total
includes taxes & fees
23 Jun - 24 Jun
Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40
Exterior

Chateau Herb ~ Miranda Carriage House Apt

Chateau Herb ~ Miranda Carriage House Apt
Ashland
9.8 out of 10, Exceptional, (8 reviews)
"Perfect huge Chateau territory! Clean rooms) quiet territory. The hosts are always available. "
United States
Irina
Chateau Herb ~ Miranda Carriage House Apt
Exterior

Chateau Herbe ~ Oberon Suite w/ Kitchen

Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland
9.4 out of 10, Exceptional, (16 reviews)
"very relaxing in a beautiful environment with easy access to the OSF and restaurants "
United States
Larry D.
The price is HK$1,262
HK$1,798 total
includes taxes & fees
15 Jun - 16 Jun
Chateau Herbe ~ Oberon Suite w/ Kitchen
Dining

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
9.4 out of 10, Exceptional, (8 reviews)
"Super nice place and great host what a gem"
United States
Robert
The price is HK$1,968
HK$2,546 total
includes taxes & fees
15 Jun - 16 Jun
Gorgeous Lakeside BarnHOUSE + SAUNA!
Dining

Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
9.8 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is HK$1,058
HK$1,879 total
includes taxes & fees
15 Jun - 16 Jun
Charming carriage house in Ashland near downtown
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$1,589
HK$2,750 total
includes taxes & fees
17 Jun - 18 Jun
Mayfield Gardens Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Interior

Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
The price is HK$1,700
HK$3,198 total
includes taxes & fees
14 Jun - 15 Jun
Savage Upon Siskiyou
Smart TV, books

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (63 reviews)
"Clean, comfortable and great location. We really enjoyed our stay and look forward to returning."
United States
Tonya W.
The price is HK$1,211
HK$2,268 total
includes taxes & fees
14 Jun - 15 Jun
Courtside Cottage - WalkScore 93 - Dog Friendly
TV, DVD player

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
Ashland
10.0 out of 10, Exceptional, (2 reviews)
"My daughter lives in the area. Five adults stayed here for 3 nights. Beautiful location! Everyone loved the hot tub"
United States
Natalie N.
The price is HK$1,168
HK$2,316 total
includes taxes & fees
22 Jun - 23 Jun
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
Fireplace

Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland
10.0 out of 10, Exceptional, (3 reviews)
"If ever I were to own a cabin, it would be of the design of this one. Rustic feel with solid and complete foundational amenities. Greats: cathedral ceiling/loft/windows, large porch, bbq, wood stove, no TV, solid internet, great shower and bathroom, firm and comfortable mattresses. Nit-picky cons: jacuzzi isn't really a traditional hot tub, 30 min drive to/from Ashland on a very winding (yet picturesque) road, check-out time of 10am with $35 fee to extend to noon. Really enjoyed our stay, will...
United States
Eric M.
The price is HK$1,994
HK$3,853 total
includes taxes & fees
29 Jun - 30 Jun
Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
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$1,154
HK$1,889 total
includes taxes & fees
15 Jun - 16 Jun
Hanna's House by WanderLodges
Exterior

Cabin #4 at Hyatt Lake Resort

Cabin #4 at Hyatt Lake Resort
Jackson County
10.0 out of 10, Exceptional, (1 review)
"Everybody here has been so nice. This has been an amazing experience we will be back. "
United States
izak p.
Cabin #4 at Hyatt Lake Resort
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$1,058
HK$1,893 total
includes taxes & fees
15 Jun - 16 Jun
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Smart TV

East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.4 out of 10, Exceptional, (49 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
East Main Downtown Bungalow
Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (225 reviews)
"Great spot, close to town, cozy and comfortable!"
United States
Carey C.
The price is HK$1,317
HK$2,246 total
includes taxes & fees
22 Jun - 23 Jun
The Ashland Cottage, walk to town
Outdoor dining

Hot tub | Sauna |Firepit |Sleeps 6!

Hot tub | Sauna |Firepit |Sleeps 6!
Ashland
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely stunning property in the hills of Ashland!"
United States
Heather K.
Hot tub | Sauna |Firepit |Sleeps 6!
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

Timbers INN and Suites

Timbers INN and Suites

10/10 Excellent
"Excellent place! Clean and cozy, comfortable bed, good location, friendly staff. Everything you need for a pleasant time in Ashland. Would absolutely stay again :)"
Julie 1-night trip
Posted less than an hour ago
Timbers INN and 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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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 renowned opera 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?

Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!: This highly rated holiday home rental in Ashland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Ashland include Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. and Chateau Herb ~ Miranda Carriage House Apt.

How many holiday rentals are there in Ashland?

Choose from 107 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 Emigrant 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.