Ashland Holiday Rentals

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Holiday Rentals in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (33)
"Terrific communication with owners, lovely property and close to downtown shops, theatre, etc. Highly recommend!"
The price is AU$453
includes taxes & fees
14 July - 15 July
A Cowslip's Belle Inn

In the historic railroad district, walking distance to all the best of Ashland!

10.0 out of 10, Exceptional, (180)
"Lovely old-fashioned cottage for friends to share"
In the historic railroad district, walking distance to all the best of Ashland!

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

10.0 out of 10, Exceptional, (45)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is AU$792
includes taxes & fees
14 July - 15 July
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

9.6 out of 10, Exceptional, (76)
"Three of us (couple and a single) enjoyed our five night stay. Location is great. Only 15 min walk to downtown and theaters. Enjoyed some great food at walkable restaurants. Cottage, although older, is nicely appointed and equipped. Would stay again if the space was needed."
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

Ashland Lodge w/ Lake Views & Game Room Loft

10.0 out of 10, Exceptional, (70)
"What an incredible property with so much history! We had a fantastic friends long weekend here - the house was well appointed and the property and surrounding land had so much room for activities. Loved our time here, and hope to come back in the future."
Ashland Lodge w/ Lake Views & Game Room Loft

Gorgeous Lakeside HOUSE + Indoor SAUNA!

8.0 out of 10, Very good, (1)
"Great family gathering fun overall! Space was a little misleading when you pulled up. The pictures gave me the impression that you had the whole space but in actuality we were only able to occupy the garage space that had been converted into a the living space. The space was pretty cool with a nice kitchen, the downside was it was not the cleanest. "
The price is AU$552
includes taxes & fees
22 July - 23 July
Gorgeous Lakeside HOUSE + Indoor SAUNA!

Railroad District, steps to downtown, everything you need to enjoy Ashland!

10.0 out of 10, Exceptional, (140)
"Could not asks for a nicer place or location."
Railroad District, steps to downtown, everything you need to enjoy Ashland!

Hanna's House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (1)
"If I were single I could live here. It's that comfortable. The freestanding apartment is ideally located and finished to a very high standard. Amazingly well designed and laid out. Full kitchen, living room, bedroom, and bath. Many, many conveniences. Cafe table in garden outside. We parked once and walked everywhere. Lovely host. Really, I can't imagine anyone giving it less than a perfect score. Would definitely stay here again."
The price is AU$349
includes taxes & fees
28 July - 29 July
Hanna's House by WanderLodges

Hot Tub! Peaceful Mountain Cabin at Hyatt Lake

8.0 out of 10, Very good, (1)
"Beautiful spot. My son and i had a lot of fun here. Perect sleeping weather at night and lucky enough to experience the mountains in a whole new way. Thank you for the opportunity to stay. Now get the water heater looked at lol."
The price is AU$476
includes taxes & fees
20 July - 21 July
Hot Tub! Peaceful Mountain Cabin at Hyatt Lake

232 4th Street

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location with easy access to downtown Ashland. We were able to walk nearly everywhere we wanted to go and enjoyed the neighborhood shops. Overall the neighborhood was quiet and the accommodations were what we wanted. "
232 4th Street

Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!

9.8 out of 10, Exceptional, (8)
"Amazing stay with beautiful views. Deep in the mountains better than expected.. would recommend to anyone looking to stay in a getaway in Ashland"
Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!

BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

9.6 out of 10, Exceptional, (67)
"My friends and I booked both the blue and pink houses and it was the perfect setup, walkable to the town and the theatres but a nice quiet area around the houses. Totally recommend and will try and come back again!"
BLOSSOM VIEW COTTAGES: Luxurious 3 Bedroom + Den Near Theaters, Downtown

Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

10.0 out of 10, Exceptional, (23)
"We arrived too late to enjoy everything this amazing property had to offer. But in the short time we were there, among the highlights were:- Singularly beautiful views to wake up to- Exceptionally comfortable beds- Super communicative and involved hosts - REALLY nice shower and bathroom"
The price is AU$392
includes taxes & fees
9 July - 10 July
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Grandview of Ashland

3.0 star property
10.0 out of 10, Exceptional, (1)
"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. "
The price is AU$736
includes taxes & fees
22 July - 23 July
Grandview of Ashland

Entire Inn | Hot Tub | Downtown Ashland | Tesla Station

The price is AU$1,681
includes taxes & fees
21 July - 22 July
Entire Inn | Hot Tub | Downtown Ashland | Tesla Station

The Red Dragon House

10.0 out of 10, Exceptional, (90)
"Great place for a visit. Just outside of town with views of the snow covered hills. "
The price is AU$313
includes taxes & fees
13 July - 14 July
The Red Dragon House

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (5)
"Great ~ memorable stay. "
The price is AU$511
includes taxes & fees
20 July - 21 July
Barclay Klum House by WanderLodges

The Mountain Ave House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (5)
"This place was great! The beds were so nice we slept amazing. Clean, and spacious. Perfect for our family. Grandma had her own space downstairs to avoid the stairs. We really just loved the comfort of the home. We will be visiting again!"
The price is AU$462
includes taxes & fees
4 Aug - 5 Aug
The Mountain Ave House by WanderLodges

Lodge Room 1 with Jacuzzi Tub at Green Springs Inn

10.0 out of 10, Exceptional, (3)
"As usual our stay here was incredible. Lots of beautiful snow and a jacuzzi tub to boot. We’ll be back."
The price is AU$380
includes taxes & fees
8 July - 9 July
Lodge Room 1 with Jacuzzi Tub at Green Springs Inn

Hiking Trail On-site: Mtn-view Eagle Point Retreat

3.0 star property
10.0 out of 10, Exceptional, (2)
"Very cute and cozy place to stay in the country. We met a bunch of wild turkey and deer in trip back and forth to home. The place was clean, inviting and privare. Enjoyed our stay!"
Hiking Trail On-site: Mtn-view Eagle Point Retreat
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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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?

In the historic railroad district, walking distance to all the best of Ashland!: This highly rated holiday home rental in Ashland is located in the city centre, and has a patio, a garden and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 Ashland Lodge w/ Lake Views & Game Room Loft and Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly.

How many holiday rentals are there in Ashland?

Choose from 132 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.