Ashland Holiday Rentals

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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Ashland holiday rentals

Living area
Barclay Klum House by WanderLodges

Holiday 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 HK$902
HK$1,994 total
includes taxes & fees
11 Jan - 12 Jan 2026
Barclay Klum House by WanderLodges
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 HK$1,050
HK$1,605 total
includes taxes & fees
15 Dec - 16 Dec
A Cowslip's Belle Inn
Sun deck
Grandview of Ashland

Holiday Home in Ashland

Grandview of Ashland
3.0 star property
10.0 out of 10, Exceptional, (2)
"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$1,521
HK$3,167 total
includes taxes & fees
7 Jan - 8 Jan 2026
Grandview of Ashland
Living area
The Mountain Ave House by WanderLodges

Holiday Home in Ashland

The Mountain Ave House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is HK$1,191
HK$2,617 total
includes taxes & fees
14 Dec - 15 Dec
The Mountain Ave House by WanderLodges
Smart TV, books, music library, stereo
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Cottage in Ashland

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
10.0 out of 10, Exceptional, (18)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is HK$1,050
HK$1,887 total
includes taxes & fees
11 Jan - 12 Jan 2026
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
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.
Cozy Ashland Studio: King Bed, 1 mile from Plaza!
Smart TV
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Holiday Home in Ashland

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
10.0 out of 10, Exceptional, (2)
"This house was so lovely and convenient. It was nice to leave the truck parked in its spot and walk to shops and restaurants. The house itself was open and comfortable with plenty of room for the both of us. And of course that kitchen had everything we could have asked for."
United States
Kami C.
The price is HK$1,018
HK$2,671 total
includes taxes & fees
2 Jan - 3 Jan 2026
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Interior detail
Hanna's House by WanderLodges

Holiday Home in Historic Railroad District

Hanna's House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (2)
"This is a true gem!!! "
United States
Deirdre
The price is HK$942
HK$1,635 total
includes taxes & fees
1 Jan - 2 Jan 2026
Hanna's House by WanderLodges
Smart TV, books
Courtside Cottage - WalkScore 93 - Dog Friendly

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (59)
"Great Location and Comfortable Unit."
United States
John V.
The price is HK$925
HK$1,873 total
includes taxes & fees
6 Jan - 7 Jan 2026
Courtside Cottage - WalkScore 93 - Dog Friendly
1 bedroom, iron/ironing board, free WiFi, bed sheets
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.

Apartment in Siskiyou-Hargadine Historic District

Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
10.0 out of 10, Exceptional, (34)
"This is the second time I’ve stayed here and I just LOVE it! You have everything needed for a relaxing break—the outside seating areas and the huge soaking tub make it extra special. Also so close to the downtown area and theater options. "
United States
Julie G.
The price is HK$630
HK$1,310 total
includes taxes & fees
14 Dec - 15 Dec
Luxuriously comfortable & peaceful getaway downtown Ashland, with views.
Interior
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Holiday 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 HK$1,113
HK$1,983 total
includes taxes & fees
14 Dec - 15 Dec
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
1 bedroom, WiFi, bed sheets
Moody Ashland Escape: Luxe Suite, Copper Tub

Holiday Home in Historic Railroad District

Moody Ashland Escape: Luxe Suite, Copper Tub
10.0 out of 10, Exceptional, (2)
"We really enjoyed our overnight stay. The place is centrally located, easy walking distance to downtown, and cozy. We loved the heated bathroom floors and the decor. Nice off street parking. Highly recommend. "
United States
Jon W.
The price is HK$1,253
HK$1,570 total
includes taxes & fees
6 Jan - 7 Jan 2026
Moody Ashland Escape: Luxe Suite, Copper Tub
Exterior
Chateau Herb ~ Miranda Carriage House Apt

Holiday Home in Ashland

Chateau Herb ~ Miranda Carriage House Apt
9.6 out of 10, Exceptional, (4)
"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$1,183
HK$1,706 total
includes taxes & fees
14 Dec - 15 Dec
Chateau Herb ~ Miranda Carriage House Apt
Dining
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.
The price is HK$805
HK$1,609 total
includes taxes & fees
21 Dec - 22 Dec
Charming carriage house in Ashland near downtown
4 bedrooms, desk, iron/ironing board, travel cot
Luxury Ashland Mountain Escape: Pool, Hot Tub

Villa in Ashland

Luxury Ashland Mountain Escape: Pool, Hot Tub
9.4 out of 10, Exceptional, (3)
"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.
The price is HK$4,193
HK$8,393 total
includes taxes & fees
14 Dec - 15 Dec
Luxury Ashland Mountain Escape: Pool, Hot Tub
Outdoor dining
Hot tub | Sauna |Firepit |Sleeps 6!

Holiday 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 HK$1,703
HK$3,679 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hot tub | Sauna |Firepit |Sleeps 6!
Iron/ironing board, travel cot, WiFi, bed sheets
Swank House -Downtown Suite- Pet Friendly

Apartment in Historic Railroad District

Swank House -Downtown Suite- Pet Friendly
10.0 out of 10, Exceptional, (4)
"My favorite Ashland stop"
United States
Andrea T.
The price is HK$1,019
HK$1,340 total
includes taxes & fees
6 Jan - 7 Jan 2026
Swank House -Downtown Suite- Pet Friendly
Fireplace
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 HK$1,121
HK$2,828 total
includes taxes & fees
14 Dec - 15 Dec
Jenny Creek Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
TV, DVD player
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.

Apartment in Ashland

Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
10.0 out of 10, Exceptional, (2)
"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$1,004
HK$2,134 total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
2 bedrooms, desk, iron/ironing board, travel cot
Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!

Apartment in Siskiyou-Hargadine Historic District

Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!
9.6 out of 10, Exceptional, (11)
"The place was amazing. Within walking distance to The Cabaret Theater and many wonderful restaurants. "
United States
Denise
The price is HK$1,124
HK$2,291 total
includes taxes & fees
14 Dec - 15 Dec
Luxurious 2 BR Red McCall Suite in historic Ashland. Features mountain views, a private deck, shared hot tub access, and a full kitchen. Sleeps 6. Walk to OSF and downtown shops/restaurants!
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
"We had a great stay! Haven’t stayed here since 2001. Happy to report that the Stratford is in great shape and the staff is still friendly, knowledgeable, and super helpful."
Amy K 3-night trip
Posted 3 days 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?

Grandview of Ashland: This highly rated holiday home rental in Ashland is located near the airport, and has a garden, 1 hot tub and a BBQ to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. Other favourite homes for rent in Ashland are New Downtown 3 Bedroom Upstairs Flat with views and Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly.

How many holiday rentals are there in Ashland?

Choose from 102 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 Ashland Library 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.