Ashland Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

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, (5 reviews)
"I absolutely fell in love with this property it was so beautiful from the moment we drove up the hill to see this gorgeous house at the top. The yard and garden was a surprise. I wasn’t expecting to have such a peaceful place to stay the pictures don’t even do it justice. I would definitely Want to stay there again when I come to visit family. "
United States
Monica
The price is HK$2,810
HK$4,274 total
includes taxes & fees
15 Mar - 16 Mar
Grandview of Ashland
Property grounds

The Red Dragon House

The Red Dragon House
Ashland
10.0 out of 10, Exceptional, (106 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$1,401
HK$1,581 total
includes taxes & fees
5 Apr - 6 Apr
The Red Dragon House
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$1,251
HK$2,347 total
includes taxes & fees
15 Mar - 16 Mar
Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
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$1,120
HK$1,645 total
includes taxes & fees
14 Mar - 15 Mar
Chateau Herb ~ Miranda Carriage House Apt
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$1,161
HK$2,231 total
includes taxes & fees
15 Mar - 16 Mar
Hot Tub! Peaceful Mountain Cabin at Hyatt Lake
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$979
HK$1,486 total
includes taxes & fees
15 Mar - 16 Mar
Chateau Herbe ~ Oberon Suite w/ Kitchen
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$1,251
HK$2,754 total
includes taxes & fees
17 Mar - 18 Mar
Homey Rustic Cabin in the Cascades
Fridge, microwave, oven, stovetop

Hot Tub! Homey Modern Cabin on Hyatt Lake 32

Hot Tub! Homey Modern Cabin on Hyatt Lake 32
Ashland
8.0 out of 10, Very good, (1 review)
"The cabin was nice, had everything we needed. The heat was turned off when we got there, took awhile for it to warm up. Extra blankets would be a nice thing to add. "
United States
Chad B.
The price is HK$1,251
HK$2,339 total
includes taxes & fees
16 Mar - 17 Mar
Hot Tub! Homey Modern Cabin on Hyatt Lake 32
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.
The price is HK$1,135
HK$1,969 total
includes taxes & fees
17 Mar - 18 Mar
Cabin #4 at Hyatt Lake Resort
Exterior

Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely perfect cabin. So cozy, full kitchen, hot tub was amazing. So convenient - thoughtfully stocked. We absolutely loved."
United States
Jenna D.
The price is HK$1,127
HK$2,828 total
includes taxes & fees
16 Mar - 17 Mar
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Fridge, microwave, oven, stovetop

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40
Ashland
9.0 out of 10, Wonderful, (4 reviews)
"It was a nice family kind of place we loved it."
United Kingdom
Nicole F.
The price is HK$1,251
HK$2,339 total
includes taxes & fees
12 Apr - 13 Apr
Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40
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$900
HK$1,732 total
includes taxes & fees
15 Mar - 16 Mar
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
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$1,010
HK$2,163 total
includes taxes & fees
19 Mar - 20 Mar
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
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$1,874
HK$3,302 total
includes taxes & fees
15 Mar - 16 Mar
The Mountain Ave House by WanderLodges
Exterior

European Style Straw Bale Retreat

European Style Straw Bale Retreat
Ashland
10.0 out of 10, Exceptional, (4 reviews)
"Our one month stay was incredible! Highly recommended. Secluded, yet very close to town. Very quiet. The hot tub was great. 5 star."
United States
Scott B.
The price is HK$1,041
HK$2,081 total
includes taxes & fees
24 Mar - 25 Mar
European Style Straw Bale Retreat
TV

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Historic Railroad District
10.0 out of 10, Exceptional, (5 reviews)
"Great location, many personal touches and the host cares about comfort! Will stay again, thanks so much! "
United States
Krista M.
The price is HK$1,712
HK$2,930 total
includes taxes & fees
14 Mar - 15 Mar
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Dining

Gorgeous Lakeside BarnHOUSE + SAUNA!

Gorgeous Lakeside BarnHOUSE + SAUNA!
Ashland
9.2 out of 10, Wonderful, (7 reviews)
"House was very clean and taken care of. A beautiful destination right across the street from lake access. Went down with a group and had an excellent stay!"
United States
Hannah D.
The price is HK$1,965
HK$2,535 total
includes taxes & fees
16 Mar - 17 Mar
Gorgeous Lakeside BarnHOUSE + SAUNA!
Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (214 reviews)
"Perfect Stay!"
United States
Anonymous traveller
The price is HK$978
HK$1,841 total
includes taxes & fees
16 Mar - 17 Mar
The Ashland Cottage, walk to town
Fireplace

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$1,127
HK$2,844 total
includes taxes & fees
15 Mar - 16 Mar
Hobart Peak Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
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, (9 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is HK$909
HK$1,755 total
includes taxes & fees
15 Mar - 16 Mar
Charming carriage house in Ashland near downtown
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

Stratford Inn

Stratford Inn

10/10 Excellent
"Clean, friendly staff, delightful stay. "
Amy 1-night trip
Posted 5 hours ago
Stratford 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 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?

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 Beautiful bungalow downtown Ashland railroad district and BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown.

How many holiday rentals are there in Ashland?

Choose from 101 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Thomas Theatre, whereas Lithia Park and Howard Prairie 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.