Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Ashland vacation rentals

Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen | Full-size fridge, microwave, oven, stovetop
Barclay Klum House by WanderLodges

Vacation Home in Ashland

Barclay Klum House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7)
"Great ~ memorable stay. "
United States
Melissa
The price is ￥17,112
￥39,855 total
includes taxes & fees
Jan 28 - Jan 29, 2026
Barclay Klum House by WanderLodges
Terrace/patio
Grandview of Ashland

Vacation Home in Ashland

Grandview of Ashland
3.0 star property
10.0 out of 10, Exceptional, (3)
"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 ￥33,678
￥62,629 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Grandview of Ashland
Main House | Terrace/patio
A Cowslip's Belle Inn

Apartment in Ashland

A Cowslip's Belle Inn
3.0 star property
9.8 out of 10, Exceptional, (40)
"Lovely yard courtyard area with koi pond"
United States
Paul
The price is ￥21,137
￥32,296 total
includes taxes & fees
Dec 29 - Dec 30
A Cowslip's Belle Inn
Exterior detail
Cozy Ashland Studio: King Bed, 1 mile from Plaza!

Apartment in Ashland

Cozy Ashland Studio: King Bed, 1 mile from Plaza!
10.0 out of 10, Exceptional, (25)
"Just what was advertised. Cozy."
United States
Weston C.
The price is ￥13,308
￥32,751 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Cozy Ashland Studio: King Bed, 1 mile from Plaza!
Grand House | Private kitchen | Full-size fridge, microwave, oven, stovetop
The Mountain Ave House by WanderLodges

Vacation Home in Ashland

The Mountain Ave House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7)
"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 ￥32,668
￥60,690 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Mountain Ave House by WanderLodges
Interior
Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Cabin in Ashland

Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
The price is ￥23,673
￥58,190 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Lobby
The Peerless Hotel | Signature Room #6 | Clawfoot Tub

Apartment in Historic Railroad District

The Peerless Hotel | Signature Room #6 | Clawfoot Tub
The price is ￥17,050
￥31,609 total
includes taxes & fees
Jan 28 - Jan 29, 2026
The Peerless Hotel | Signature Room #6 | Clawfoot Tub
Outdoor spa tub
Chateau Herb ~ Miranda Carriage House Apt

Vacation Home in Ashland

Chateau Herb ~ Miranda Carriage House Apt
9.6 out of 10, Exceptional, (5)
"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 ￥26,460
￥37,346 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Chateau Herb ~ Miranda Carriage House Apt
Fridge, microwave, oven, stovetop
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Vacation Home in Ashland

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
10.0 out of 10, Exceptional, (3)
"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 ￥19,806
￥47,168 total
includes taxes & fees
Jan 22 - Jan 23, 2026
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Exterior
Owl Creek Cabin Mountain Getaway near Ashland, Oregon

Cabin in Ashland

Owl Creek Cabin Mountain Getaway near Ashland, Oregon
2.0 star property
The price is ￥30,453
￥34,745 total
includes taxes & fees
Dec 29 - Dec 30
Owl Creek Cabin Mountain Getaway near Ashland, Oregon
Exterior
Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn

Cabin in Ashland

Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
10.0 out of 10, Exceptional, (3)
"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 ￥23,673
￥58,190 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Pilot Rock Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Microwave, oven, stovetop, dishwasher
Charming carriage house in Ashland near downtown

Cottage in Skidmore Academy Historic District

Charming carriage house in Ashland near downtown
10.0 out of 10, Exceptional, (6)
"Enjoyed our stay"
United States
Julie M.
Charming carriage house in Ashland near downtown
City Bungalow, Garden Area | Private kitchen | Oven, stovetop, dishwasher, toaster
Hanna's House by WanderLodges

Vacation Home in Historic Railroad District

Hanna's House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (3)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is ￥18,377
￥32,535 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hanna's House by WanderLodges
Terrace/patio
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Vacation Home in Ashland

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
10.0 out of 10, Exceptional, (31)
"Our stay was amazing everything"
United States
annie t.
The price is ￥23,814
￥41,654 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
Terrace/patio
Quaint Downtown Ashland Studio- pet friendly!

Apartment in Ashland

Quaint Downtown Ashland Studio- pet friendly!
9.2 out of 10, Wonderful, (13)
"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 ￥13,308
￥32,751 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Quaint Downtown Ashland Studio- pet friendly!
TV
3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.

Apartment in Historic Downtown District

3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.
The price is ￥25,051
￥59,274 total
includes taxes & fees
Jan 8 - Jan 9, 2026
3 bedrooms include a king and two queen size beds, 2 bathrooms, and kitchenette.
Exterior
Homey Rustic Cabin in the Cascades

Cabin in Jackson County

Homey Rustic Cabin in the Cascades
10.0 out of 10, Exceptional, (1)
"Great location cabin was perfect for a group large upstairs sleeping areas. Outside was great "
United Kingdom
Troy K.
The price is ￥25,028
￥53,987 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Homey Rustic Cabin in the Cascades
Outdoor dining
Hot tub | Sauna |Firepit |Sleeps 6!

Vacation Home in Ashland

Hot tub | Sauna |Firepit |Sleeps 6!
10.0 out of 10, Exceptional, (3)
"Great home in a nice location with a wonderful view. Well-appointed and clean. "
United States
Ryan G.
The price is ￥34,273
￥75,210 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hot tub | Sauna |Firepit |Sleeps 6!
Interior
The Ashland Cottage, walk to town

Cottage in Siskiyou-Hargadine Historic District

The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (211)
"Great location and comfortable accommodations. This is our second time staying here."
United States
Kathleen P.
The price is ￥26,147
￥44,867 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Ashland Cottage, walk to town
Outdoor dining
Swank Suites | King with Lux Tub

Vacation Home in Historic Railroad District

Swank Suites | King with Lux Tub
The price is ￥20,511
￥26,362 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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

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 vacation rentals in Ashland?

Yes, we have vacation rentals in Ashland close to ScienceWorks Hands-On Museum, or you can choose a more secluded option if you want a relaxing stay. Visitors to Ashland like the picturesque gardens and acclaimed theater 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 vacation rentals that Ashland has to offer?

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette. : This highly rated vacation home rental in Ashland is located in the mountains and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a microwave. Some other homes for rent in Ashland include New Downtown 3 Bedroom Upstairs Flat with views and Gorgeous Lakeside HOUSE + Indoor SAUNA!.

How many vacation rentals are there in Ashland?

Choose from 102 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Oregon Shakespeare Festival, whereas Lithia Park and North Mountain Park 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 vacation rentals like in Ashland?

Vacation rentals are privately owned properties you can reserve for a short or long stay in Ashland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.