Jackson County Holiday Rentals

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Top Holiday Rentals Destinations in Jackson County

Hiking
Union Creek Resort
Union Creek Resort
3.0 star property
8.0 out of 10, Very good, (907)
"Beautiful location near Crater Lake. Lots of short scenic hikes nearby. "
United States
karen
Union Creek Resort
House
Enchanting Getaway: Farmhouse and Tiny House Duo
Enchanting Getaway: Farmhouse and Tiny House Duo
2.0 star property
The price is NZ$411
includes taxes & fees
5 Nov - 6 Nov
Enchanting Getaway: Farmhouse and Tiny House Duo
Exterior
Cowgirl Craftsman - Private Suite Upstairs - 2 blocks Historic Downtown J'ville
Cowgirl Craftsman - Private Suite Upstairs - 2 blocks Historic Downtown J'ville
2.0 star property
9.8 out of 10, Exceptional, (7)
"The room was open and spacious, nicely decorated, welcoming and comfortable. It was also within walking distance from the concert I came to attend locally!"
United States
Cheryl
The price is NZ$399
includes taxes & fees
5 Nov - 6 Nov
Cowgirl Craftsman - Private Suite Upstairs - 2 blocks Historic Downtown J'ville
Luxury House, 2 Bedrooms, Bathtub, Garden Area | Private kitchen
Barclay Klum House by WanderLodges
Barclay Klum House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (6)
"Hannah was such a good communicator and so helpful for my husband and I… We were in Ashland to visit friends and it was such a great place to be. So centrally located but also spacious and clean and beautiful… We would stay there anytime and hope to stay there again"
United States
Eileen
The price is NZ$528
includes taxes & fees
13 Nov - 14 Nov
Barclay Klum House by WanderLodges
Deluxe Suite | Living area
The Rellik House and Winery
The Rellik House and Winery
3.5 star property
9.4 out of 10, Exceptional, (3)
"Beautiful property on the winery. Nicely decorated room & large shower. Separate living, kitchenette & bedroom area. The only downside is the room we had had the parking area on one side & the winery tasting room on the other. So we kept our curtains closed. Also the hot tub was dirty. We were looking forward to using it. "
United States
Laurel
The price is NZ$427
includes taxes & fees
4 Dec - 5 Dec
The Rellik House and Winery
Terrace/patio
Grandview of 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. "
United States
Monica
The price is NZ$1,037
includes taxes & fees
12 Nov - 13 Nov
Grandview of Ashland
Glamp Cottage Trailer | Living area
Paschal Winery
Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (13)
"It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland."
United States
Heidi
The price is NZ$308
includes taxes & fees
5 Nov - 6 Nov
Paschal Winery
Cottage (1 Bedroom) | Interior
On-site Winery & Tasting Room: Oregon Bungalow!
On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
8.4 out of 10, Very good, (5)
"Was A nice oasis deer came and visited me in the morning, and the view was outstanding!"
United States
Samona
The price is NZ$374
includes taxes & fees
5 Nov - 6 Nov
On-site Winery & Tasting Room: Oregon Bungalow!
Family House, Kitchen, Garden View | Private kitchen
Lanka Rose House by WanderLodges
Lanka Rose House by WanderLodges
3.5 star property
10.0 out of 10, Exceptional, (1)
"Very cute house with all the necessities for a cozy stay. "
United States
Roxanne
The price is NZ$436
includes taxes & fees
18 Nov - 19 Nov
Lanka Rose House by WanderLodges
Main House | Terrace/patio
A Cowslip's Belle Inn
A Cowslip's Belle Inn
3.0 star property
9.8 out of 10, Exceptional, (39)
"This place is serene, beautiful and has a perfect location for walking downtown"
United States
Seth
The price is NZ$362
includes taxes & fees
16 Nov - 17 Nov
A Cowslip's Belle Inn
Studio, 1 Queen Bed, Kitchenette | Private kitchenette
Rosewood Studio by WanderLodges
Rosewood Studio by WanderLodges
3.0 star property
The price is NZ$349
includes taxes & fees
5 Nov - 6 Nov
Rosewood Studio by WanderLodges
4 bedrooms
Enchanting Getaway Farmhouse and Tiny House Duo
Enchanting Getaway Farmhouse and Tiny House Duo
2.0 star property
The price is NZ$939
includes taxes & fees
6 Nov - 7 Nov
Enchanting Getaway Farmhouse and Tiny House Duo
Terrace/patio
The Shady Knoll - Peace & Quiet near the Rogue River!
The Shady Knoll - Peace & Quiet near the Rogue River!
10.0 out of 10, Exceptional, (7)
"The Shady Knoll is a modern, clean and well-equipped house for cooking or cocktails on the patio with a hot tub. Watch the wildlife go by and enjoy the beautiful area. The owner was great at communication and was very helpful. We'd love to come back and check out the different seasons. "
United States
Cheryl F.
The price is NZ$480
includes taxes & fees
9 Nov - 10 Nov
The Shady Knoll - Peace & Quiet near the Rogue River!
Exterior
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
2.0 star property
10.0 out of 10, Exceptional, (15)
"Great spot, mainly quiet with beautiful flower garden. Well equipped kitchen and appliances. Nice open space for family. Centrally located for access to Rogue Valley destinations."
United States
Gretchen W. S.
The price is NZ$377
includes taxes & fees
5 Nov - 6 Nov
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
Exterior
The Red Dragon House
The Red Dragon House
10.0 out of 10, Exceptional, (102)
"Mike and Mindy's place had everything we could ask for and more."
United States
Carol C.
The price is NZ$355
includes taxes & fees
5 Dec - 6 Dec
The Red Dragon House
Grand House | Private kitchen
The Mountain Ave House by WanderLodges
The Mountain Ave House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7)
"This place was great! The beds were so nice we slept amazing. Clean, and spacious. Perfect for our family. Grandma had her own space downstairs to avoid the stairs. We really just loved the comfort of the home. We will be visiting again!"
United States
Arturo
The price is NZ$765
includes taxes & fees
16 Nov - 17 Nov
The Mountain Ave House by WanderLodges
2 bedrooms, desk, iron/ironing board, travel cot
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
10.0 out of 10, Exceptional, (2)
"This house was so lovely and convenient. It was nice to leave the truck parked in its spot and walk to shops and restaurants. The house itself was open and comfortable with plenty of room for the both of us. And of course that kitchen had everything we could have asked for."
United States
Kami C.
The price is NZ$663
includes taxes & fees
8 Nov - 9 Nov
Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen
Property grounds
Red Barn in Wine Country
Red Barn in Wine Country
9.6 out of 10, Exceptional, (8)
"This was a great place to stay. Loved the animals and river access for fishing and swimming. Winery next door was a plus too. "
United States
Beth J.
The price is NZ$493
includes taxes & fees
7 Nov - 8 Nov
Red Barn in Wine Country
Microwave, oven, stovetop, dishwasher
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
10.0 out of 10, Exceptional, (17)
"great location and we were able to walk to everything we wanted to do in Ashland, clean unit and quiet, clear rules."
United States
Cynthia K.
The price is NZ$709
includes taxes & fees
17 Nov - 18 Nov
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Fridge, oven, stovetop, dishwasher
Station House Suite A
Station House Suite A
9.8 out of 10, Exceptional, (22)
"Beautiful & comfortable place to stay in an excellent location. Thank you for the great memories, can’t wait to stay here again!"
United States
Daniel
The price is NZ$770
includes taxes & fees
5 Nov - 6 Nov
Station House Suite A
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 Jackson County Hotel Reviews

Clarion Pointe Medford

Clarion Pointe Medford

10/10 Excellent
"Nice, clean room with a comfy bed. Check in clerk was courteous and friendly. Breakfast has a great selection. Would definitely stay here again "
Christel 1-night trip
Posted 2 days ago
Clarion Pointe Medford

Find out more about Jackson County

Everything you need to know about Jackson County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Jackson County holiday rental for you. At Expedia, you can take your pick from private holiday 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 Jackson County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Jackson County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jackson County. 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 Jackson County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Jackson County holiday rentals we have selected for you start as low as NZ$237 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Jackson County rentals

At Expedia, we put the best Jackson County holiday 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 Jackson County 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 Jackson County holiday.

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