Ashland Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Tonight
May 2 - May 3
Tomorrow
May 3 - May 4
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Holiday Rentals in Ashland

Secluded Forest Log House 15 minutes to Ashland
Interior
Secluded Forest Log House 15 minutes to Ashland
10.0 out of 10, Exceptional, (36)
"We had such an amazing time at the cabin! Originally we were planning on eloping at Lithia Park, but once we saw the beautiful mountains and scenery at the property we changed our minds, and had our ceremony at the viewpoint. Thank you so much for your hospitality and allowing us to tie the knot on your gorgeous land!"
Secluded Forest Log House 15 minutes to Ashland
Studio Sanctuary: Welcoming to Pets
1 bedroom, iron/ironing board, travel cot, free WiFi
Studio Sanctuary: Welcoming to Pets
10.0 out of 10, Exceptional, (6)
"Nicely appointed, comfortable, efficient unit. So great to have a sofa for reading and lounging between plays and dining. In a quiet neighborhood, yet close (beautiful walk along stream) to downtown and Lithia Park."
The price is HK$649
per night
3 Jun - 4 Jun
Studio Sanctuary: Welcoming to Pets
Courtside Cottage - WalkScore 93 - Dog Friendly
Fridge, microwave, coffee/tea maker, toaster
Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (22)
"I had a chance to stay at the “Courtside” cottage for 2 weeks. Everything was well appointed, the bedding was of top quality sheets and pillows and the kitchen was very efficient. Many great touches and thought was taken to all the details and information about the cottage as well as things to do in town. It’s in a very private location and the entrance and parking was off the main street but was very walkable to the shops and restaurants. Communication with Michael, the owner, was very good. I...
The price is HK$1,098
per night
6 May - 7 May
Courtside Cottage - WalkScore 93 - Dog Friendly
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Fridge, microwave, oven, stovetop
Railroad District, steps to downtown, everything you need to enjoy Ashland!
10.0 out of 10, Exceptional, (129)
"Had the best stay in Ashland; went everywhere. The leaves were brilliant and bright."
Railroad District, steps to downtown, everything you need to enjoy Ashland!
The Red Dragon House
Exterior
The Red Dragon House
10.0 out of 10, Exceptional, (65)
"We highly recommend Mike and Mindy's spacious 2 bedroom property. They had the most thorough instructional manual we've ever seen, and additionally had clearly labeled drawers and cabinets in the kitchen and bathroom making it easy to find whatever we needed. We met the delightful Mindy out on her spacious grounds with her incredible dogs, and enjoyed our morning coffee on the covered back porch looking out at the trees and distant hills. Would definitely return!"
The price is HK$1,367
per night
14 May - 15 May
The Red Dragon House
Charming home, w/hot tub, close to downtown Pet-Friendly!
Property grounds
Charming home, w/hot tub, close to downtown Pet-Friendly!
10.0 out of 10, Exceptional, (19)
"Our family had an amazing time staying here. We went hiking in Lithia Park, shopped in downtown Ashland, and saw plays. We were able to have a Passover Seder thanks to the well equipped kitchen and dining area. We had seven family members sleepover, and everybody slept Beautifully. The house has fun artwork and decorations and many pieces of furniture for storage. Next time we bring swimsuits to enjoy the hot tub."
Charming home, w/hot tub, close to downtown Pet-Friendly!
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station
Outdoor spa tub
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station
10.0 out of 10, Exceptional, (2)
"We only had two nights only one full day in Ashland and what a full day it was, the park was beautiful the restaurants the fun shops. on and on. Your place was great wonderful locality. We really enjoyed ourselves and your beautiful Inn!"
The price is HK$1,004
per night
5 May - 6 May
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station
Hyatt Praire Mountain Cabin
Exterior
Hyatt Praire Mountain Cabin
10.0 out of 10, Exceptional, (42)
"It was a very nice restful visit."
The price is HK$1,407
per night
5 May - 6 May
Hyatt Praire Mountain Cabin
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Dining
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
10.0 out of 10, Exceptional, (2)
"Absolutely perfect cabin. So cozy, full kitchen, hot tub was amazing. So convenient - thoughtfully stocked. We absolutely loved."
The price is HK$1,259
per night
8 May - 9 May
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Ashland Lodge w/ Lake Views & Game Room Loft
Exterior
Ashland Lodge w/ Lake Views & Game Room Loft
10.0 out of 10, Exceptional, (64)
"We had a week at this home for our bridal party. It was an incredible space that really allowed everyone to get to know each other and deeply enjoyed the space."
Ashland Lodge w/ Lake Views & Game Room Loft
Creekside Cabin--a quiet, wooded country delight
Outdoor dining
Creekside Cabin--a quiet, wooded country delight
10.0 out of 10, Exceptional, (156)
"It was a delightful stay for my dog and me because: The cabin was charming with all of its period details, The property was walkable and peaceful with a "creek running through it", and The host was outgoing, warm and friendly. The resident dog, too! Wish we could have stayed longer. Would definitely book the cabin again."
Creekside Cabin--a quiet, wooded country delight
Stunning Medford Escape w/ Panoramic Views!
Fridge, microwave, stovetop, dishwasher
Stunning Medford Escape w/ Panoramic Views!
10.0 out of 10, Exceptional, (24)
"Cathy is Great, The home is a giant older single story Family Home with a basement full of beds and air hocky table, Huge kitchen and dining room, Hot tub, Pool, alot of toys for the pool, garage, even entry gates to the property its fenced, and surrounded by wild turkeys and deer ! It was really nice ! and they allow your Dogs ! Thanks Again Cathy!"
Stunning Medford Escape w/ Panoramic Views!
Private Cabin, Dock & Hot Tub~Ski& Fish Copco Lake
Outdoor spa tub
Private Cabin, Dock & Hot Tub~Ski& Fish Copco Lake
10.0 out of 10, Exceptional, (46)
"Just the right size for a relaxing getaway. Beautiful area. Enjoyed the house and host was very accommodating. Would definitely stay again."
The price is HK$1,183
per night
5 May - 6 May
Private Cabin, Dock & Hot Tub~Ski& Fish Copco Lake
Southern Oregon Gem (EV Charger)
Fridge, microwave, oven, stovetop
Southern Oregon Gem (EV Charger)
10.0 out of 10, Exceptional, (27)
"The accommodations were great and very comfortable. We couldn't find any information about WiFi in the house though, and when I sent a message to the host, asking if there was WiFi his response was "yes" without any further information. Otherwise no complaints!"
The price is HK$548
per night
7 May - 8 May
Southern Oregon Gem (EV Charger)
A Cowslip's Belle Inn
Terrace/patio
A Cowslip's Belle Inn
3.0 star property
9.8 out of 10, Exceptional, (9)
"This place is absolutely amazing. I stayed for a long weekend/Mt bike trip and really enjoyed it. Quiet, peaceful setting and close to everything. "
The price is HK$923
per night
9 May - 10 May
A Cowslip's Belle Inn
Hyatt Lake Mountain Retreat
Fridge, microwave, oven, stovetop
Hyatt Lake Mountain Retreat
9.8 out of 10, Exceptional, (64)
"Cozy little cabin with a great view of the lake. My family and I enjoyed our time unplugging from the world. We had a very Merry Christmas 🎄"
Hyatt Lake Mountain Retreat
Ashland's Mountain View Vacation Rental.
Exterior
Ashland's Mountain View Vacation Rental.
9.8 out of 10, Exceptional, (20)
"We were in Ashland for a conference at Southern Oregon University. The Mountain View rental was clean, spacious and well equipped. Beds were comfortable."
The price is HK$1,563
per night
5 May - 6 May
Ashland's Mountain View Vacation Rental.
1930s Queen Anne Historic Downtown Retreat
Exterior
1930s Queen Anne Historic Downtown Retreat
9.8 out of 10, Exceptional, (22)
"A very fun, quaint and cozy house. Loved the homey feel and big kitchen table especially."
The price is HK$774
per night
14 May - 15 May
1930s Queen Anne Historic Downtown Retreat
Blue Gate Cottage on the Rogue River
Exterior
Blue Gate Cottage on the Rogue River
9.8 out of 10, Exceptional, (16)
"We loved the area and the cabin"
Blue Gate Cottage on the Rogue River
Ashland: Steps from the Shakespeare Festival
Smart TV, books
Ashland: Steps from the Shakespeare Festival
9.6 out of 10, Exceptional, (8)
"Great location, walking distance to city center arts and restaurants. Older property is charming, clean and well maintained, but sorely needs updating and substantive renovation (v photo impression)."
The price is HK$1,001
per night
20 May - 21 May
Ashland: Steps from the Shakespeare Festival
Don't see what you're looking for?
See all available properties in Ashland
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.

Other types of properties in Ashland you may be interested in

Ashland Springs Hotel
Garden
Ashland Springs Hotel
3.0 star property
9.2 out of 10, Wonderful, (1001)
"I liked just about everything. I was not driving and the bus stop was just there and the staff helped me get my bags to the bus stop. The restaurant was incredibly good and not that expensive. "
The price is HK$1,288
per night
13 May - 14 May
Ashland Springs Hotel
Stratford Inn
Exterior detail
Stratford Inn
2.5 star property
9.0 out of 10, Wonderful, (1506)
"Amazing place. Close to walk down town. Salt water pool was thr best after a long day "
The price is HK$899
per night
12 May - 13 May
Stratford Inn
Ashland Hills Hotel & Suites
Lobby
Ashland Hills Hotel & Suites
3.0 star property
9.0 out of 10, Wonderful, (1546)
"Loved it! Very nice property"
The price is HK$1,049
per night
19 May - 20 May
Ashland Hills Hotel & Suites
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.

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 lively festivals this destination is known for. Leave some time to check out the acclaimed theatre scene and top-notch restaurants during your visit.

What are some of the best holiday rentals that Ashland has to offer?

Secluded Forest Log House 15 minutes to Ashland: This highly rated holiday home rental in Ashland is located in the mountains, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other homes for rent in Ashland include Charming Retreat: Ashland's Urban Hideaway and The Red Dragon House.

How many holiday rentals are there in Ashland?

Choose from 91 Expedia holiday rentals in Ashland for a memorable holiday.

What can I see and do in Ashland?

Cultural attractions include Allen Elizabethan Theatre and Angus Bowmer Theatre, whereas Lithia Park and Emigrant 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.

Recent reviews of Ashland properties
Expedia verified reviews

Callahan's Mountain Lodge

Callahan's Mountain Lodge

5/5 Excellent
"We liked Everything"
A verified traveller stayed at Callahan's Mountain Lodge
Posted 1 day ago
Callahan's Mountain Lodge