Ashland Vacation Rentals

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Vacation Rentals in Ashland

Hyatt Lake Mountain Retreat

9.8 out of 10, Exceptional, (81)
"The cabin was comfortable, clean, and our family of four had plenty of room. We would certainly book again!"
Hyatt Lake Mountain Retreat

Ashland Lodge w/ Lake Views & Game Room Loft

10.0 out of 10, Exceptional, (73)
"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

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (35)
"What a wonderful place to stay! The owners were very cordial and offered suggestion about places to go. We particularly loved to Koi pond right off our deck. "
The price is CA $268
CA $376 total
includes taxes & fees
Aug 14 - Aug 15
A Cowslip's Belle Inn

Chateau Herb ~ Miranda Carriage House Apt

10.0 out of 10, Exceptional, (3)
"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."
The price is CA $203
CA $297 total
includes taxes & fees
Aug 19 - Aug 20
Chateau Herb ~ Miranda Carriage House Apt

Barclay Klum House by WanderLodges

4.0 star property
10.0 out of 10, Exceptional, (5)
"Great ~ memorable stay. "
The price is CA $205
CA $407 total
includes taxes & fees
Sep 1 - Sep 2
Barclay Klum House by WanderLodges

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

10.0 out of 10, Exceptional, (48)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is CA $279
CA $707 total
includes taxes & fees
Aug 18 - Aug 19
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

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

10.0 out of 10, Exceptional, (186)
"Lovely old-fashioned cottage for friends to share"
In the historic railroad district, walking distance to all the best of Ashland!

Hyatt Prairie Mountain Cabin

10.0 out of 10, Exceptional, (56)
"Great cabin , loved our stay"
The price is CA $223
CA $535 total
includes taxes & fees
Aug 14 - Aug 15
Hyatt Prairie Mountain Cabin

Chateau Herbe ~ Oberon Suite w/ Kitchen

9.6 out of 10, Exceptional, (14)
"This was such a beautiful property and our suite was so clean! We will be back :)"
The price is CA $234
CA $333 total
includes taxes & fees
Aug 14 - Aug 15
Chateau Herbe ~ Oberon Suite w/ Kitchen

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40

10.0 out of 10, Exceptional, (1)
"Very comfortable will definitely be staying again."
The price is CA $201
CA $386 total
includes taxes & fees
Sep 8 - Sep 9
Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40

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

10.0 out of 10, Exceptional, (26)
"This is a beautiful space in a beautiful setting. Everything was comfortable, clean, modern, functional, and beautiful! I didn't realize this was attached to the owner's home when I booked it, but it wasn't awkward at all. The space is private and separate. Enjoying the view from the front porch was a relaxing highlight at night. We loved staying here!"
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.

Hot Tub! Peaceful Mountain Cabin at Hyatt Lake

9.0 out of 10, Wonderful, (2)
"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 CA $215
CA $407 total
includes taxes & fees
Aug 14 - Aug 15
Hot Tub! Peaceful Mountain Cabin at Hyatt Lake

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 CA $174
CA $302 total
includes taxes & fees
Aug 17 - Aug 18
Hanna's House by WanderLodges

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

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

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

10.0 out of 10, Exceptional, (142)
"A very comfortable space with easy access to theaters and restaurants."
Railroad District, steps to downtown, everything you need to enjoy Ashland!

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 CA $394
CA $694 total
includes taxes & fees
Sep 1 - Sep 2
Grandview of Ashland

Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat

3.5 star property
Sunset Chalet - 2600 Sq.ft. Multi-seasonal Retreat

Whispering Pines Cabin Retreat

3.5 star property
Whispering Pines Cabin Retreat

Ashland Lodge w/ Lake Views & Game Room Loft

3.0 star property
Ashland Lodge w/ Lake Views & Game Room Loft
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

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?

Barclay Klum House by WanderLodges: This highly rated vacation home rental in Ashland is located near the airport and has a private yard, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. Our travelers also rate Ashland Lodge w/ Lake Views & Game Room Loft as a favorite home for rent in Ashland.

How many vacation rentals are there in Ashland?

Choose from 130 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 Emigrant Lake 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.