Ashland Vacation Rentals

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Vacation Rentals in Ashland

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 $230
CA $422 total
includes taxes & fees
May 22 - May 23
Courtside Cottage - WalkScore 93 - Dog Friendly
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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 $238
CA $275 total
includes taxes & fees
May 23 - May 24
The Red Dragon House
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 $177
CA $313 total
includes taxes & fees
May 19 - May 20
Queen Suite | Hot Tub | Downtown Ashland | Tesla Station
Exterior
Hyatt Praire Mountain Cabin
10.0 out of 10, Exceptional, (42)
"It was a very nice restful visit."
The price is CA $245
CA $558 total
includes taxes & fees
Jun 15 - Jun 16
Hyatt Praire Mountain Cabin
Property grounds
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 CA $306
CA $734 total
includes taxes & fees
May 20 - May 21
Charming home, w/hot tub, close to downtown Pet-Friendly!
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 28 - May 29
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
Outdoor dining
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
Outdoor spa tub
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 CA $209
CA $434 total
includes taxes & fees
May 20 - May 21
Private Cabin, Dock & Hot Tub~Ski& Fish Copco Lake
Fridge, microwave, stovetop, dishwasher
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!
Fridge, microwave, oven, stovetop
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 CA $104
CA $186 total
includes taxes & fees
May 20 - May 21
Southern Oregon Gem (EV Charger)
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 $236
CA $475 total
includes taxes & fees
May 23 - May 24
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
Exterior
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
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 $419 total
includes taxes & fees
May 22 - May 23
Downtown Ashland Pet-Friendly Haven
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
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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, (1518)
"The HVAC unit in the room was loud."
The price is CA $136
CA $152 total
includes taxes & fees
May 23 - May 24
Stratford Inn
Lobby
Ashland Hills Hotel & Suites
3.0 star property
9.0 out of 10, Wonderful, (1539)
"We always enjoy staying here! The facility is wonderful as is the staff!"
The price is CA $182
CA $203 total
includes taxes & fees
May 30 - May 31
Ashland Hills Hotel & Suites
Exterior
Best Western Windsor Inn
2.5 star property
9.0 out of 10, Wonderful, (1001)
"Great place to stay!"
The price is CA $190
CA $212 total
includes taxes & fees
May 23 - May 24
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.

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Ashland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Ashland vacation rentals we have selected for you start as low as CA $109 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

5/5 Excellent
"We always enjoy staying here! The facility is wonderful as is the staff!"
A verified traveller stayed at Ashland Hills Hotel & Suites
Posted 11 hours ago
Ashland Hills Hotel & Suites