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Holiday Rentals in Jackson County

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Top Cities in Jackson County

Holiday RentalsHoliday Rentals

Central Point

Central Point
Holiday RentalsHoliday Rentals

Prospect

Prospect

Our top choices for Jackson County holiday rentals

Luxury House, 2 Bedrooms, Bathtub, Garden Area | Living area
Barclay Klum House by WanderLodges

Holiday Home in Ashland

Barclay Klum House by WanderLodges
4.0 star property
10.0 out of 10, Exceptional, (7)
"Great ~ memorable stay. "
United States
Melissa
The price is €236
includes taxes & fees
2 Jan - 3 Jan 2026
Barclay Klum House by WanderLodges
Glamp Cottage Trailer | Living area
Paschal Winery

Cottage in Talent

Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (15)
"Very nice and hassle free check in "
United States
Matthew
The price is €192
includes taxes & fees
28 Dec - 29 Dec
Paschal Winery
Cottage (1 Bedroom) | Interior
On-site Winery & Tasting Room: Oregon Bungalow!

Cottage in Central Point

On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
8.4 out of 10, Very good, (5)
"Loved our stay at the Bungalow. The owners were so welcoming, helpful and friendly. The bungalow was very clean and had well equipped. It wa a great location for everything we wanted to do. The bungalow was even nicer than the pictures. We would definitely recommend this stay! "
United States
Deborah
The price is €188
includes taxes & fees
22 Dec - 23 Dec
On-site Winery & Tasting Room: Oregon Bungalow!
Exterior
Rosie's Woodland Paradise! Come relax and rejuvenate!

Cabin in Gold Hill

Rosie's Woodland Paradise! Come relax and rejuvenate!
10.0 out of 10, Exceptional, (129)
"Rosie was amazing! Her soup was delicious and her hospitality was top notch!! I highly recommend staying at Rosie’s!!"
United States
Heather N.
The price is €143
includes taxes & fees
3 Jan - 4 Jan 2026
Rosie's Woodland Paradise! Come relax and rejuvenate!
Property grounds
Serene Historic Cabin, Nine Acre Estate, Just Off I-5

Cabin in Gold Hill

Serene Historic Cabin, Nine Acre Estate, Just Off I-5
9.6 out of 10, Exceptional, (42)
"Great place for a friends getaway"
United States
Jan G.
The price is €146
includes taxes & fees
18 Jan - 19 Jan 2026
Serene Historic Cabin, Nine Acre Estate, Just Off I-5
Coffee and/or coffee maker
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Cottage in Central Point

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.8 out of 10, Exceptional, (102)
"Super cute place! Perfectly located in the middle of things. Food and drink near by."
United States
Rachel B.
The price is €141
includes taxes & fees
1 Jan - 2 Jan 2026
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Interior
Little Wolf Tiny Home cozy, pet friendly, secluded

Apartment in Central Point

Little Wolf Tiny Home cozy, pet friendly, secluded
10.0 out of 10, Exceptional, (4)
"everything was advertised, nice and quite, well maintained and kept. Would stay again."
Canada
william L.
The price is €127
includes taxes & fees
22 Dec - 23 Dec
Little Wolf Tiny Home cozy, pet friendly, secluded
Deluxe Suite | Living area
The Rellik House and Winery

Holiday Home in Central Point

The Rellik House and Winery
3.5 star property
9.4 out of 10, Exceptional, (3)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is €208
includes taxes & fees
18 Jan - 19 Jan 2026
The Rellik House and Winery
Dining
Charming carriage house in Ashland near downtown

Cottage in Skidmore Academy Historic District

Charming carriage house in Ashland near downtown
10.0 out of 10, Exceptional, (6)
"Enjoyed our stay"
United States
Julie M.
Charming carriage house in Ashland near downtown
Terrace/patio
Newly renovated studio with farm and mountain view’s! 5 minutes to Jacksonville.

Apartment in Medford

Newly renovated studio with farm and mountain view’s! 5 minutes to Jacksonville.
9.8 out of 10, Exceptional, (26)
"Super cute place! Loved staying here. The door was hard to unlock and lock, but even with that loved staying here. "
United States
Kristine S.
The price is €146
includes taxes & fees
22 Dec - 23 Dec
Newly renovated studio with farm and mountain view’s! 5 minutes to Jacksonville.
1 bedroom, iron/ironing board, WiFi, bed sheets
Hillcrest Nest

Apartment in Medford

Hillcrest Nest
9.8 out of 10, Exceptional, (14)
"Location was great and the accommodations had pretty much everything you need to stay comfortably. Had a wonderful conversation with the residence of the main house."
United States
andrew u.
The price is €153
includes taxes & fees
23 Dec - 24 Dec
Hillcrest Nest
Interior
Private Queen Room w/ Bathroom

Holiday Home in White City

Private Queen Room w/ Bathroom
10.0 out of 10, Exceptional, (8)
"Very nice place to stay."
United States
Anonymous traveller
The price is €99
includes taxes & fees
22 Dec - 23 Dec
Private Queen Room w/ Bathroom
Fridge, microwave, oven, stovetop
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer

Holiday Home in Medford

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, (17)
"Great place to stay. Very comfortable beds & very clean. "
United States
Tiffany F.
The price is €186
includes taxes & fees
4 Jan - 5 Jan 2026
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
Interior
Black Pearl - Apartment near the river

Apartment in rogue river

Black Pearl - Apartment near the river
9.8 out of 10, Exceptional, (19)
"Beautiful place! Dishwasher was broken but otherwise we loved it!"
United States
Burt H.
The price is €203
includes taxes & fees
3 Jan - 4 Jan 2026
Black Pearl - Apartment near the river
Exterior
Cowgirl Craftsman - Private King Suite Upstairs - Historic Downtown J'ville

Holiday Home in Jacksonville Historic District

Cowgirl Craftsman - Private King Suite Upstairs - Historic Downtown J'ville
2.0 star property
9.8 out of 10, Exceptional, (7)
"Cozy, warm, and inviting stay here for an anniversary getaway. Lots of things in walking distance. Wonderful hostess and wonderful stay. We would definitely come back!"
United States
Kristi
The price is €199
includes taxes & fees
22 Dec - 23 Dec
Cowgirl Craftsman - Private King Suite Upstairs - Historic Downtown J'ville
Exterior
Cozy Tiny House! Small But Mighty ~ Comfy & Gorgeous Location

Holiday Home in Central Point

Cozy Tiny House! Small But Mighty ~ Comfy & Gorgeous Location
10.0 out of 10, Exceptional, (10)
"I had a lovely stay at the Bee home! I loved the location and how peaceful it was! The place had everything one would need in a clean and compact package. I was able to see the meteor shower on my second night there. I would definitely stay there again!"
United States
Shannon S.
Cozy Tiny House! Small But Mighty ~ Comfy & Gorgeous Location
Sun deck
Grandview of Ashland

Holiday Home in Ashland

Grandview of Ashland
3.0 star property
10.0 out of 10, Exceptional, (2)
"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 €435
includes taxes & fees
3 Jan - 4 Jan 2026
Grandview of Ashland
Smart TV, books
Courtside Cottage - WalkScore 93 - Dog Friendly

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (59)
"Great stay. Loved the location and the host was super great. "
United States
Aaron B.
Courtside Cottage - WalkScore 93 - Dog Friendly
35-inch Smart TV with digital channels, Netflix, Hulu
Lanka Rose House by WanderLodges

Holiday Home in Phoenix

Lanka Rose House by WanderLodges
3.5 star property
10.0 out of 10, Exceptional, (2)
"Very cute house with all the necessities for a cozy stay. "
United States
Roxanne
The price is €220
includes taxes & fees
30 Dec - 31 Dec
Lanka Rose House by WanderLodges
Dining
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

Apartment in Trail

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
9.2 out of 10, Wonderful, (15)
"We enjoyed a quiet evening. Everything was kept tidy and was a good place for us to stop for the evening."
United States
Mary P.
The price is €172
includes taxes & fees
1 Jan - 2 Jan 2026
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
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

Ramada by Wyndham Medford Airport North

Ramada by Wyndham Medford Airport North

10/10 Excellent
"The staff is amazingly kind and helpful. The room was very clean and tidy. The bed in my room was a bit loud, the base is aluminum. The other hotel guests were very loud, but that’s not anything the hotel can do much about. The friendly service is top notch and more than expected. "
Robin 1-night trip
Posted 2 days ago
Ramada by Wyndham Medford Airport North

Find out more about Jackson County

Holiday Homes in Jackson County

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