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Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured Cottages in Southern Oregon

Glamp Cottage Trailer | Terrace/patio
Paschal Winery

Cottage in Talent

4.5 star property
9.6 out of 10, Exceptional, (14)
"Very nice and hassle free check in "
United States
Matthew
The price is AU$325
includes taxes & fees
14 Dec - 15 Dec
Paschal Winery
House (1 Bedroom) | Interior
Fish & Hike: Peaceful Cabin on Williamson River

Cottage in Chiloquin

3.0 star property
The price is AU$495
includes taxes & fees
3 Dec - 4 Dec
Fish & Hike: Peaceful Cabin on Williamson River
Outdoor dining
R&R on the Rogue River! This 2 BR cottage in Gold Hill features a private hot tub with stunning scenic views. Enjoy a spacious, private setting perfect for relaxation, adventure, or remote work

Cottage in Gold Hill

9.4 out of 10, Exceptional, (16)
"The place was super cute and updated. The hot tub had been cleaned and refilled with fresh water, which was very nice. I feel we had some trouble with the keypad which should be looked into. Other than that it was a great quiet weekend. Will rent again for sure."
United States
Michele R.
The price is AU$343
includes taxes & fees
3 Dec - 4 Dec
R&R on the Rogue River! This 2 BR cottage in Gold Hill features a private hot tub with stunning scenic views. Enjoy a spacious, private setting perfect for relaxation, adventure, or remote work
Exterior
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Cottage in Central Point

9.8 out of 10, Exceptional, (100)
"I travel to Central Point regularly, and this was my second stay at this lovely gem. I'll be back again. Clean, bright, and comfortable. "
United States
Mike W.
The price is AU$273
includes taxes & fees
3 Dec - 4 Dec
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior
Downtown Mint

Cottage in Medford

9.8 out of 10, Exceptional, (40)
"Loved the house, had a great stay!"
United States
Kara B.
The price is AU$344
includes taxes & fees
14 Dec - 15 Dec
Downtown Mint
Terrace/patio
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Cottage in Central Point

9.8 out of 10, Exceptional, (26)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
The price is AU$356
includes taxes & fees
12 Dec - 13 Dec
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior
The Vintage Cottage with riverfront access

Cottage in Grants Pass

9.8 out of 10, Exceptional, (110)
"We just loved staying in this wonderful cottage! The host was so kind and was able to recommend several ideas during our stay. It was well-stocked with tea, coffee, yummy snacks and the fluffiest of towels! We will definitely stay here again!"
United States
Marguerite
The price is AU$257
includes taxes & fees
4 Dec - 5 Dec
The Vintage Cottage with riverfront access
Fridge, microwave, coffee/tea maker, toaster
Courtside Cottage - WalkScore 93 - Dog Friendly

Cottage in Historic Railroad District

10.0 out of 10, Exceptional, (59)
"Great Location and Comfortable Unit."
United States
John V.
The price is AU$317
includes taxes & fees
8 Dec - 9 Dec
Courtside Cottage - WalkScore 93 - Dog Friendly
Property grounds
Charming carriage house in Ashland near downtown

Cottage in Skidmore Academy Historic District

10.0 out of 10, Exceptional, (6)
"Enjoyed our stay"
United States
Julie M.
The price is AU$319
includes taxes & fees
11 Dec - 12 Dec
Charming carriage house in Ashland near downtown
Exterior
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

Cottage in Jacksonville

9.8 out of 10, Exceptional, (32)
"We loved the animals and how peaceful it was there,The owner was very accommodating and nice. Highly recommend if I ever need to stay in the area again this would be my first pick "
United States
Ryan K.
The price is AU$339
includes taxes & fees
3 Dec - 4 Dec
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Outdoor spa tub
Charming 2 BR riverside stopover in Gold Hill. Private hot tub, river access, and just down the road from Del Rio Vineyards. Perfect base for exploring the Rogue Valley. Pet-friendly!

Cottage in Gold Hill

10.0 out of 10, Exceptional, (22)
"The hot tub was awesome, gorgeous of the river. Situated nicely between Medford and Grants pass with a short drive to either. Hosts were communicative and pleasant. All necessities that could be reasonably expected on site. Shower has great water pressure. "
United States
Alexis B.
The price is AU$327
includes taxes & fees
6 Dec - 7 Dec
Charming 2 BR riverside stopover in Gold Hill. Private hot tub, river access, and just down the road from Del Rio Vineyards. Perfect base for exploring the Rogue Valley. Pet-friendly!
Cottage (1 Bedroom) | Interior
On-site Winery & Tasting Room: Oregon Bungalow!

Cottage in Central Point

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 AU$336
includes taxes & fees
3 Dec - 4 Dec
On-site Winery & Tasting Room: Oregon Bungalow!
Exterior
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Cottage in Ashland

10.0 out of 10, Exceptional, (18)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is AU$276
includes taxes & fees
3 Dec - 4 Dec
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Exterior
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

Cottage in City Center Medford

9.6 out of 10, Exceptional, (22)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is AU$364
includes taxes & fees
7 Dec - 8 Dec
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Cottage in Central Point

10.0 out of 10, Exceptional, (3)
"Booking and check-in were very smooth. The property is as advertised and more! Peaceful, beautiful, comfortable and convenient to Jacksonville and nearby areas. Will look forward to staying again. "
United States
Ruth P.
The price is AU$305
includes taxes & fees
13 Dec - 14 Dec
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Cottage in Jacksonville Historic District

10.0 out of 10, Exceptional, (45)
"This place was awesome. Perfect location for walking to restaurants and Britt. The whole place was very clean. Looking forward to staying again"
United States
Ellen H.
The price is AU$472
includes taxes & fees
8 Dec - 9 Dec
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
Exterior
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience

Cottage in Central Point

The price is AU$448
includes taxes & fees
1 Jan - 2 Jan 2026
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
Exterior
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

Cottage in Jacksonville Historic District

10.0 out of 10, Exceptional, (1)
"The location was amazing: within walking distance of almost all the Jacksonville restaurants, stores, residential areas and the Britt Festival. The cottage was very cleaned and well-maintained. Ashley was very responsive and helpful in making all the arrangements for our party."
United States
Juliana S.
The price is AU$555
includes taxes & fees
6 Dec - 7 Dec
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior
The Ashland Cottage, walk to town

Cottage in Siskiyou-Hargadine Historic District

10.0 out of 10, Exceptional, (210)
"The property was beautiful and just as described. We were rewarded with a kitty visit on the deck in the mornings while we drank our tea and coffee. Perfect distance from town, able to walk but not in all of the hubbub. "
United States
Jeanette S.
The price is AU$415
includes taxes & fees
3 Dec - 4 Dec
The Ashland Cottage, walk to town
Exterior
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains

Cottage in Central Point

8.8 out of 10, Excellent, (9)
"This place was amazing. Took a little extra time to get to, but it was well worth it. Would definitely stay here again. Thanks again for all necessary accommodations as well. Definitely appreciated 🙏"
United States
Silent Tunez P.
The price is AU$320
includes taxes & fees
3 Dec - 4 Dec
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
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 Southern Oregon Hotel Reviews

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
"Staff was fabulous (Crystal), and the room is great. Thank you!"
Charles 1-night trip
Posted 2 days ago
Flagship Inn of Ashland

Find out more about Southern Oregon

Southern Oregon Cottages information

Number of reviews
696
Accommodation
198 Cottages
Lowest Price
AU$257
Highest Price
AU$555

Frequently asked questions

How much do cottages in Southern Oregon cost?
Cottages in Southern Oregon range between AU$257 and AU$555 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southern Oregon?
You can choose from 198 cottages in Southern Oregon. Whether you're travelling with the whole family, as a twosome or with a group of best friends, Expedia is here to help you find the perfect place.
What is there to do in Southern Oregon near my cottage?
Whether you like dining, sightseeing, museums or malls, Southern Oregon has something to suit all tastes! The awesome city of Medford boasts lots of activities and attractions, including EdenVale Winery, Craterian Ginger Rogers Theatre and Childrens Museum. If you're taking off to Jacksonville, Quady North, Britt Pavilion and Sarah Zigler Interpretive Trail have to be on your itinerary.

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