Ashland Vacation Rentals

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Browse Select Ashland Vacation Homes

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (83)
"Accommodation was perfect. Comfortable beds. Adorable decorative home. Loved the special touch with cheese platter and wine when we arrived. Returning in July. "
ZZ ZANY ZOO II - Townhome, with Carport & Garage

Quiet and peaceful cottage close to downtown

9.8 out of 10, Exceptional, (51)
"Plants, 70s vinyl, a few antiques, nicely updated, clean, private backyard, good location, did I mention 70s vinly"
The price is CA $256
CA $459 total
includes taxes & fees
Apr 23 - Apr 24
Quiet and peaceful cottage close to downtown

New house with king beds and 3 full bathrooms

9.4 out of 10, Exceptional, (29)
"I will be staying here every time I come to Medford. "
The price is CA $226
CA $421 total
includes taxes & fees
Apr 21 - Apr 22
New house with king beds and 3 full bathrooms

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

10.0 out of 10, Exceptional, (36)
"The hot tub stopped working a few mins after we jumped in. Other than that, the property was great and we'd stay here again."
The price is CA $312
CA $750 total
includes taxes & fees
Apr 24 - Apr 25
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

The Original ZZ ZANY ZOO Townhome, with Carport & Garage #1

10.0 out of 10, Exceptional, (181)
"Beautiful cozy place to spend your time away from home. "
The Original ZZ ZANY ZOO Townhome, with Carport & Garage #1

Tastefully remodeled 3 bedroom 2 bath home with large private back yard

10.0 out of 10, Exceptional, (38)
"Very nice experience, will stay next time in the area."
The price is CA $249
CA $541 total
includes taxes & fees
Apr 22 - Apr 23
Tastefully remodeled 3 bedroom 2 bath home with large private back yard

Large Private Carriage-House Retreat with Amazing Views

10.0 out of 10, Exceptional, (121)
"We had a wonderful stay in Medford. Great location and great host!"
Large Private Carriage-House Retreat with Amazing Views

Great, clean house in the middle of Medford

9.0 out of 10, Wonderful, (46)
"Enough room for our family of 5. We didn’t realize it was part of a two dwelling property, but the listing itself was private/separated from other dwelling. "
The price is CA $180
CA $446 total
includes taxes & fees
Apr 21 - Apr 22
Great, clean house in the middle of Medford

Cedar Wood Mountain View Retreat

10.0 out of 10, Exceptional, (3)
"We rented the house during Christmas break and it was absolutely wonderful for our large family. Everyone had enough sleeping space, the house was clean, cozy, and welcoming. The view of the mountains and countryside is also a plus! Everything worked out - and the hot tub was a nice addition. The house is even stocked with toys and books for children and plenty of towels and linens. We enjoyed cooking in kitchen as well. This is a great spot! "
Cedar Wood Mountain View Retreat

Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.

9.6 out of 10, Exceptional, (39)
"House was amazing, stayed with family and new grand baby. Everything you could need and the split level was perfect for us! Definitely will rent again next time were in Medford. "
Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.

Comfy Cozy Casa

10.0 out of 10, Exceptional, (44)
"We had a great experience at this property and it was close in proximity to an event that we attended."
The price is CA $152
CA $380 total
includes taxes & fees
Apr 30 - May 1
Comfy Cozy Casa

Sun Cottage Downtown Jacksonville

10.0 out of 10, Exceptional, (16)
"We came to discover Jacksonville and it did not disappoint. We were a block away from downtown so we walked to explore and dine out. The house was great right on the corner with a nice lawn great for our Josie (dog). It was well supplied with everything you need to enjoy the house. Check in and check out was so easy. Recommend it with high makes…"
The price is CA $223
CA $443 total
includes taxes & fees
Apr 21 - Apr 22
Sun Cottage Downtown Jacksonville

Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.

10.0 out of 10, Exceptional, (12)
"Patricia's home was absolutely wonderful! While enjoying coffee on the patio, we were treated to lovely views of the creek as well as watching the heron in a nest at the top of a nearby tree feed her nestlings, the many mallards and wood ducks feeding below in the creek, the largest squirrel I have ever seen(!), and a plethora of mockingbirds, jaybirds, gold finches and others frequenting the feeder. The fire pit was wonderful for the evenings. The cottage has such a warm and lovely aura about...
Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.

Cozy, dog-friendly 3-bedroom fully stocked home in Medford with AC, WiFi

9.8 out of 10, Exceptional, (8)
"My family loved your home…me too! All of the extra goodies for the dog and them were very appreciated. Thank you Amanda for having this be a Wonderful place to visit!"
The price is CA $222
CA $414 total
includes taxes & fees
Apr 21 - Apr 22
Cozy, dog-friendly 3-bedroom fully stocked home in Medford with AC, WiFi

Beautifully Renovated Sleeps up to 8 in East Medford

10.0 out of 10, Exceptional, (1)
"We were in town for a funeral and needed a place kind of last minute. Host was very responsive and quick to reply. House was perfect! Very clean home, plenty of towels and kitchen utensils. Had everything we need. Location is great, near shopping and food. Quiet neighborhood. Will definitely stay again next time we're in town. "
Beautifully Renovated Sleeps up to 8 in East Medford

Ashland Lodge w/ Lake Views & Game Room Loft

10.0 out of 10, Exceptional, (68)
"Our family and friends had the best time. Would recommend to anyone that is looking for some peace and quiet. "
Ashland Lodge w/ Lake Views & Game Room Loft

Spacious home with pool nestled in the foothills of RoxyAnn.

10.0 out of 10, Exceptional, (18)
"Place was great. Don’t need all the vrbo email."
Spacious home with pool nestled in the foothills of RoxyAnn.

Beautiful Luxury Cottage. Walk To It All!

10.0 out of 10, Exceptional, (116)
"Upon entering the home, we were greeted with Christmas music, heated rooms, and snack treats. Jackie was always quick to respond to our few questions and had provided lots of information about the area. We spent our days exploring Jacksonville and Ashland, and the location of the house made this so convenient. We were able to take an evening walk to enjoy the Christmas lights in town and the neighborhood. Such a wonderful stay! We will certainly stay here again."
Beautiful Luxury Cottage. Walk To It All!

Main Residence: 5 beds, 5 baths, sleeping porches, & full kitchen.

9.6 out of 10, Exceptional, (5)
"Our family of 10, parents, their children and grandchildren, came to spend the holidays together. We had a great time in a fabulous property with plenty of room to all gather for meals and games or have some quiet time in our own space. Everyone enjoyed the adjacent coffee shop and tasting room complete with games. Several close options for hiking and groceries were just a mile or two away."
The price is CA $622
CA $1,210 total
includes taxes & fees
Apr 21 - Apr 22
Main Residence: 5 beds, 5 baths, sleeping porches, & full kitchen.

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

10.0 out of 10, Exceptional, (17)
"Cozy comfortable stay, very well equipped home. The hosts were very responsive and helpful. "
The price is CA $220
CA $367 total
includes taxes & fees
Apr 21 - Apr 22
Casual luxury retreat: Siskiyou Mountain Place. 2 br, kitchenette.
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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Other property types in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (31)
"Lovely place and the room had everything I needed. "
The price is CA $208
CA $309 total
includes taxes & fees
Apr 21 - Apr 22
A Cowslip's Belle Inn

East Main Downtown Bungalow

9.2 out of 10, Wonderful, (26)
"We really enjoyed our short stay here! The cottage is clean, in a great location for walking to OSF and great food, and in a good neighborhood. Communication with the owner/manager was very easy and they were responsive to our few questions. We hope to return in 2025 for a longer visit!"
The price is CA $180
CA $363 total
includes taxes & fees
Apr 21 - Apr 22
East Main Downtown Bungalow

Quiet and peaceful cottage close to downtown

9.8 out of 10, Exceptional, (51)
"Plants, 70s vinyl, a few antiques, nicely updated, clean, private backyard, good location, did I mention 70s vinly"
The price is CA $256
CA $459 total
includes taxes & fees
Apr 23 - Apr 24
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.