Ashland Vacation Rentals

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May 14 - May 15
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May 15 - May 16
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May 17 - May 19
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May 24 - May 26

Vacation Rentals in Ashland

Smart TV, books
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 CA $171
CA $420 total
includes taxes & fees
May 20 - May 21
Downtown Ashland Pet-Friendly Haven
Main House | 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 CA $161
CA $361 total
includes taxes & fees
May 15 - May 16
A Cowslip's Belle Inn
Fridge, microwave, oven, stovetop
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
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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!
Exterior
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 CA $273
CA $521 total
includes taxes & fees
May 20 - May 21
Ashland's Mountain View Vacation Rental.
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 CA $217
CA $405 total
includes taxes & fees
May 15 - May 16
Courtside Cottage - WalkScore 93 - Dog Friendly
1 bedroom, iron/ironing board, travel crib, free WiFi
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 CA $135
CA $239 total
includes taxes & fees
May 18 - May 19
Pet-Friendly Studio Serenity
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
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 CA $239
CA $276 total
includes taxes & fees
May 15 - May 16
The Red Dragon House
Property grounds
The Dogwood Suite at Tudor House Vacation Rentals
9.4 out of 10, Exceptional, (89)
"Was wonderful to be able to walk into town toeat or enjoy the happenings."
The Dogwood Suite at Tudor House Vacation Rentals
Outdoor spa tub
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 CA $176
CA $315 total
includes taxes & fees
May 19 - May 20
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station
Interior
Hyatt Praire Mountain Cabin
10.0 out of 10, Exceptional, (42)
"It was a very nice restful visit."
The price is CA $246
CA $556 total
includes taxes & fees
Jun 2 - Jun 3
Hyatt Praire Mountain Cabin
Property grounds
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
Smart TV, books
City Comfort: Your Ashland Retreat
The price is CA $172
CA $284 total
includes taxes & fees
Jun 7 - Jun 8
City Comfort: Your Ashland Retreat
Property grounds
Urban Oasis: 3BDR Walkable Gem
9.4 out of 10, Exceptional, (3)
"Wonderful house, close to town. Easy communication."
The price is CA $194
CA $483 total
includes taxes & fees
May 27 - May 28
Urban Oasis: 3BDR Walkable Gem
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 CA $220
CA $411 total
includes taxes & fees
May 15 - May 16
Soda Mountain Cabin w/ Jacuzzi and Wood Stove at Green Springs Inn
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
Kayaking
Rocky Point Resort
2.5 star property
8.0 out of 10, Very good, (245)
"Very rustic. More of a cabin than hotel room. TV didn’t work. Internet did work. Heater worked good enough. Staff very friendly and tried to help. "
The price is CA $122
CA $138 total
includes taxes & fees
May 15 - May 16
Rocky Point Resort
Exterior
Harriman Springs Resort Cabin 3 - Cabins with a View
9.4 out of 10, Exceptional, (113)
"Had a lovely birthday dinner. Jasmine (cook and server) was extremely capable and friendly. The cabins are well designed with top quality materials. Beautiful area near Klamath Lake."
The price is CA $205
CA $254 total
includes taxes & fees
May 20 - May 21
Harriman Springs Resort Cabin 3 - Cabins with a View
Exterior
Harriman Springs Resort Cabin 2 - Cabins with a View
9.2 out of 10, Wonderful, (75)
"Beautiful, modern, stunning views, gorgeous bathroom, clean, cozy, memorable."
The price is CA $205
CA $256 total
includes taxes & fees
May 27 - May 28
Harriman Springs Resort Cabin 2 - Cabins with a View
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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.

Ashland Vacation Rental Travel Info

Number of vacation rentals
56
Popular accommodation
Ashland private vacation homes
Known landmarks
Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre
International airports
Medford, OR (MFR-Rogue Valley Intl.) and Ashland, OR (AHM-Sumner Parker Field)

Other types of properties in Ashland you may be interested in

Exterior detail
Stratford Inn
2.5 star property
9.0 out of 10, Wonderful, (1516)
"We stayed 3 nights 5/8-5/11, 2 Q Mt View room—very clean; enough space to not feel cramped; very comfortable firm beds; lots of drawers and surfaces; refrig had a good sized freezer; AC was efficient and quiet; included breakfast better and more varied than the typical free breakfast, and in a large area with lots of natural light, and friendly staff. Close to Lithia Park area. Highly recommended. Only suggestion: Add one or two more luggage carts for check in and check out usage. "
The price is CA $137
CA $152 total
includes taxes & fees
May 20 - May 21
Stratford Inn
Lobby
Ashland Hills Hotel & Suites
3.0 star property
9.0 out of 10, Wonderful, (1536)
"Pretty routine overnight going to Portland from S.F. Checkin was efficient. Room basic but clean and comfortible. We enjoyed courtesy breakfast but did not otherwise use cafe."
The price is CA $183
CA $204 total
includes taxes & fees
May 29 - May 30
Ashland Hills Hotel & Suites
Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio
Callahan's Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (1000)
"Breakfast was so-so. "
The price is CA $178
CA $181 total
includes taxes & fees
May 16 - May 17
Callahan's Mountain Lodge
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.

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.

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?

Secluded Forest Log House 15 minutes to Ashland: This highly rated vacation home rental in Ashland is located in the mountains and has a patio, a garden, and a barbecue grill 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 vacation with amenities like 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 vacation rentals are there in Ashland?

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

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 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.

Recent reviews of Ashland properties
Expedia verified reviews

Callahan's Mountain Lodge

Callahan's Mountain Lodge

5/5 Excellent
"Breakfast was so-so. "
A verified traveller stayed at Callahan's Mountain Lodge
Posted 17 hours ago
Callahan's Mountain Lodge