Ashland Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Ashland vacation rentals

Sundeck

Vacation Home in Ashland

Grandview of Ashland
3.0 star property
10.0 out of 10, Exceptional, (5 reviews)
"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 CA $409
CA $663 total
includes taxes & fees
Mar 9 - Mar 10
Grandview of Ashland
Terrace/patio

Cabin in Jackson County

Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
10.0 out of 10, Exceptional, (4 reviews)
"One night stay, very peaceful "
United Kingdom
Joshua S.
The price is CA $219
CA $410 total
includes taxes & fees
Mar 9 - Mar 10
Hot Tub! Quiet Comfy Cabin at Hyatt Lake 44
Property grounds

Vacation Home in Ashland

The Red Dragon House
10.0 out of 10, Exceptional, (106 reviews)
"House was definitely pet friendly. Dogs always enjoy staying there. Very relaxing place. Beds are comfortable. House is always clean excellent place to stay"
United States
karen
The price is CA $245
CA $282 total
includes taxes & fees
Mar 6 - Mar 7
The Red Dragon House
Outdoor dining

Cabin in Jackson County

Hot Tub! Peaceful Mountain Cabin at Hyatt Lake
9.4 out of 10, Exceptional, (3 reviews)
"This was our second time staying at this cabin. Once again it was an amazing trip. We really enjoyed our quiet peaceful nights in the hot tub. Celebrated Thanksgiving there it was exactly what we wanted. Can’t wait for our next trip. "
United States
Taryn T.
The price is CA $203
CA $393 total
includes taxes & fees
Mar 9 - Mar 10
Hot Tub! Peaceful Mountain Cabin at Hyatt Lake
Exterior

Vacation Home in Ashland

Chateau Herb ~ Miranda Carriage House Apt
9.6 out of 10, Exceptional, (5 reviews)
"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 CA $208
CA $300 total
includes taxes & fees
Mar 6 - Mar 7
Chateau Herb ~ Miranda Carriage House Apt
Exterior

Cabin in Jackson County

Homey Rustic Cabin in the Cascades
10.0 out of 10, Exceptional, (1 review)
"Great location cabin was perfect for a group large upstairs sleeping areas. Outside was great "
United Kingdom
Troy K.
The price is CA $219
CA $481 total
includes taxes & fees
Mar 9 - Mar 10
Homey Rustic Cabin in the Cascades
Exterior

Apartment in Ashland

Chateau Herbe ~ Oberon Suite w/ Kitchen
9.4 out of 10, Exceptional, (16 reviews)
"very relaxing in a beautiful environment with easy access to the OSF and restaurants "
United States
Larry D.
The price is CA $196
CA $289 total
includes taxes & fees
Mar 9 - Mar 10
Chateau Herbe ~ Oberon Suite w/ Kitchen
Exterior

Vacation Home in Jackson County

Cabin #4 at Hyatt Lake Resort
10.0 out of 10, Exceptional, (1 review)
"Everybody here has been so nice. This has been an amazing experience we will be back. "
United States
izak p.
The price is CA $198
CA $345 total
includes taxes & fees
Mar 9 - Mar 10
Cabin #4 at Hyatt Lake Resort
Fridge, microwave, oven, stovetop

Cabin in Ashland

Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40
9.0 out of 10, Wonderful, (4 reviews)
"It was a nice family kind of place we loved it."
United Kingdom
Nicole F.
The price is CA $219
CA $410 total
includes taxes & fees
Mar 9 - Mar 10
Hot Tub! Relaxing Tranquil Cabin at Hyatt Lake 40
Fridge, microwave, oven, stovetop

Cabin in Ashland

Hot Tub! Homey Modern Cabin on Hyatt Lake 32
8.0 out of 10, Very good, (1 review)
"The cabin was nice, had everything we needed. The heat was turned off when we got there, took awhile for it to warm up. Extra blankets would be a nice thing to add. "
United States
Chad B.
The price is CA $219
CA $410 total
includes taxes & fees
Mar 9 - Mar 10
Hot Tub! Homey Modern Cabin on Hyatt Lake 32
TV, DVD player

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 reviews)
"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 CA $176
CA $379 total
includes taxes & fees
Mar 9 - Mar 10
Hyatt Prairie Cabin offers views and a two person Hot Tub! Both bedrooms have a queen size bed.
Fireplace

Cabin in Ashland

Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely perfect cabin. So cozy, full kitchen, hot tub was amazing. So convenient - thoughtfully stocked. We absolutely loved."
United States
Jenna D.
The price is CA $197
CA $497 total
includes taxes & fees
Mar 9 - Mar 10
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Living area

Vacation Home in Ashland

Barclay Klum House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is CA $179
CA $382 total
includes taxes & fees
Mar 15 - Mar 16
Barclay Klum House by WanderLodges
Smart TV, books

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (62 reviews)
"Great place to stay very quaint very clean. Host is very gracious and communicated perfectly before the trip. Definitely would stay here again."
United States
Lantz B.
The price is CA $145
CA $313 total
includes taxes & fees
Mar 5 - Mar 6
Courtside Cottage - WalkScore 93 - Dog Friendly
Interior detail

Vacation Home in Historic Railroad District

Hanna's House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (3 reviews)
"Thoughtfully arranged and provisioned. A hidden gem."
United States
Jerald
The price is CA $162
CA $286 total
includes taxes & fees
Mar 5 - Mar 6
Hanna's House by WanderLodges
Dining

Cabin in Ashland

Hobart Peak Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
10.0 out of 10, Exceptional, (1 review)
"This place exceeded expectations. Very clean, well maintained, and well built cabin with a loft and jacuzzi tub. The restaurant was closed, but the Hyatt was 8 minutes away, and was told by the helpful person there that the restaurant will open again soon. Will definitely look to book another say during winter."
United States
Ryan G.
The price is CA $197
CA $497 total
includes taxes & fees
Mar 9 - Mar 10
Hobart Peak Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
Fridge, microwave, oven, stovetop

Vacation Home in Ashland

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
10.0 out of 10, Exceptional, (64 reviews)
"Perfect spot.We really enjoyed our stay."
United States
Cecilia K.
The price is CA $198
CA $599 total
includes taxes & fees
Mar 7 - Mar 8
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Smart TV

Vacation Home in Ashland

Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
10.0 out of 10, Exceptional, (3 reviews)
"Lovely stay in a nicely restored historic home. We were very comfortable and the location is great in central Ashland."
United States
Casey K.
The price is CA $194
CA $445 total
includes taxes & fees
Mar 15 - Mar 16
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Exterior detail

Apartment in Ashland

Cozy Ashland Studio: King Bed, 1 mile from Plaza!
10.0 out of 10, Exceptional, (25 reviews)
"Our out of town in-laws loved their stay. We highly recommend it!"
United States
Alessandro C.
The price is CA $109
CA $277 total
includes taxes & fees
Mar 6 - Mar 7
Cozy Ashland Studio: King Bed, 1 mile from Plaza!
Fridge, microwave, oven, stovetop

Vacation Home in Siskiyou-Hargadine Historic District

Quiet and peaceful cottage close to downtown
9.8 out of 10, Exceptional, (65 reviews)
"The property was very pleasant and clean... great directions to get to it, friendly host, sweet outdoor space, clean and welcoming. "
United States
Sue P.
The price is CA $171
CA $345 total
includes taxes & fees
Mar 6 - Mar 7
Quiet and peaceful cottage close to downtown
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

Ashland Springs Hotel

Ashland Springs Hotel

10/10 Excellent
"Will be returning. Fantastic historic hotel, holding on to its history. "
Matthew 3-night trip
Posted 7 hours ago
Ashland Springs Hotel

Find out more about Ashland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Ashland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

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

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

Premier Downstairs Flat in Perfect Down Town Location : This highly rated vacation home rental in Ashland is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other homes for rent in Ashland include Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly and Beautiful bungalow downtown Ashland railroad district.

How many vacation rentals are there in Ashland?

Choose from 102 Expedia vacation rentals in Ashland for a memorable vacation.

What can I see and do in Ashland?

Cultural attractions include Thomas Theatre and Oregon Shakespeare Festival, whereas Lithia Park and Howard Prairie 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.