Ashland Holiday Rentals

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Holiday Rentals in Ashland

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!
Ashland's Mountain View Vacation Rental.
10.0 out of 10, Exceptional, (21)
"Place was a perfect fit for our group! Definitely would stay here again!"
The price is NZ$631
includes taxes & fees
20 May - 21 May
Ashland's Mountain View Vacation Rental.
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 NZ$512
includes taxes & fees
22 May - 23 May
Courtside Cottage - WalkScore 93 - Dog Friendly
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Pet-Friendly Studio Serenity
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 NZ$291
includes taxes & fees
18 May - 19 May
Pet-Friendly Studio Serenity
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
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 NZ$334
includes taxes & fees
22 May - 23 May
The Red Dragon House
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station
10.0 out of 10, Exceptional, (2)
"Lovely location, very clean and comfortable. Highly recommmend."
The price is NZ$380
includes taxes & fees
19 May - 20 May
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station
Hyatt Praire Mountain Cabin
10.0 out of 10, Exceptional, (42)
"It was a very nice restful visit."
The price is NZ$679
includes taxes & fees
19 May - 20 May
Hyatt Praire Mountain Cabin
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."
The price is NZ$892
includes taxes & fees
19 May - 20 May
Charming home, w/hot tub, close to downtown Pet-Friendly!
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 NZ$498
includes taxes & fees
16 May - 17 May
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
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
10.0 out of 10, Exceptional, (157)
"I absolutely love the Creekside Cabin. I come to the area for work a lot and it’s perfect when I get to spend my time here. So please don’t tell anyone!! It’s so quiet and my little dog can run around with Monte. I can watch the deer walking along the edge of the property in evening. Life is sweet at the tiny cabin."
Creekside Cabin--a quiet, wooded country delight
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 NZ$500
includes taxes & fees
16 May - 17 May
Private Cabin, Dock & Hot Tub~Ski& Fish Copco Lake
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!
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 NZ$225
includes taxes & fees
20 May - 21 May
Southern Oregon Gem (EV Charger)
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 NZ$578
includes taxes & fees
22 May - 23 May
A Cowslip's Belle Inn
Hyatt Lake Mountain Retreat
9.8 out of 10, Exceptional, (65)
"The house was so cozy and comfortable. A sit on the porch swing and the lovely view of the prairie and lake! Host was so helpful and so accommodating!!"
Hyatt Lake Mountain Retreat
Blue Gate Cottage on the Rogue River
9.8 out of 10, Exceptional, (17)
"So grateful for the quality of this place that takes pets! When someone is staying in the Lodge next door it’s good to at least meet each other, and cooperate to share the outdoor spaces. Plenty of room for everyone. Lovely part of the Rogue Valley."
Blue Gate Cottage on the Rogue River
Downtown Ashland Pet-Friendly Haven
9.6 out of 10, Exceptional, (9)
"We stayed for a week and it met all our needs. We loved the location, the beds were comfortable, the house was very clean and we felt safe. Thanks for a relaxing stay."
The price is NZ$510
includes taxes & fees
22 May - 23 May
Downtown Ashland Pet-Friendly Haven
The Maple Apartment at Tudor House Vacation Rentals
9.6 out of 10, Exceptional, (127)
"The property was clean and conveniently located."
The Maple Apartment at Tudor House Vacation Rentals
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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

Stratford Inn
2.5 star property
9.0 out of 10, Wonderful, (1518)
"We stay at Stratford Inn everytime we visit Ashland. Friendly staff and its an easy walk to everything in downtown Ashland. The shower has great water pressure and our room is always clean. "
The price is NZ$185
includes taxes & fees
19 May - 20 May
Stratford Inn
Ashland Hills Hotel & Suites
3.0 star property
9.0 out of 10, Wonderful, (1538)
"It’s a charming and well kept hotel ~ quiet, safe and clean. Thank you! "
The price is NZ$248
includes taxes & fees
29 May - 30 May
Ashland Hills Hotel & Suites
Best Western Windsor Inn
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Ryan was great and helped me get my room quickly "
The price is NZ$258
includes taxes & fees
21 May - 22 May
Best Western Windsor Inn
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.

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.