A town nestled in a valley with a prominent building in the foreground and hills in the background.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Southern Oregon cottages

An outdoor patio with a grill, dining table, chairs, and string lights.

1. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
The price is AU$578
includes taxes & fees
3 Nov - 4 Nov
Paschal Winery
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

2. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, this was a very clean, attractive property with everything needed. Maricio was the host & he was very attentive, kind & quick to respond . I highly recommend this property, it’s in a nice area & fun places to explore. Thanks for a great visit!"
United States
Jayne
The price is AU$319
includes taxes & fees
15 Nov - 16 Nov
Forest Cabin by Crater Lake & Klamath Falls
A house with a wooden deck, a stone wall, and a wooden fence.

3. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is AU$403
includes taxes & fees
3 Nov - 4 Nov
The Ashland Cottage, walk to town
Coffee and/or coffee maker

4. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Central Point
9.8 out of 10, Exceptional, (129 reviews)
"Wonderful stay and will definitely do so again!!!"
United States
Kelly B.
The price is AU$242
includes taxes & fees
3 Nov - 4 Nov
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A residential house with a garage, a satellite dish, and a driveway.

5. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (14 reviews)
"Lovely stay. "
United States
Cyndy K.
The price is AU$302
includes taxes & fees
29 Nov - 30 Nov
Charming carriage house in Ashland near downtown
A house with a yellow door, a stone facade, and a garden with various flowers.

6. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (52 reviews)
"Good location and comfy beds!"
United States
Melissa L.
The price is AU$298
includes taxes & fees
3 Nov - 4 Nov
Downtown Mint
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

7. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (77 reviews)
"Great cottage in an awesome location!"
United States
Andrea R.
The price is AU$349
includes taxes & fees
30 Nov - 1 Dec
Courtside Cottage - WalkScore 93 - Dog Friendly
A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

8. Rosewood Studio | Private Cottage Near Downtown

Rosewood Studio | Private Cottage Near Downtown
Medford
8.0 out of 10, Very good, (1 review)
"Location was as advertised."
United States
william L.
Rosewood Studio | Private Cottage Near Downtown
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

9. Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Central Point
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful peaceful place with a great view. Host was accommodating and the house was clean and we enjoyed the art and decorations."
United States
Elizabeth W.
The price is AU$270
includes taxes & fees
8 Nov - 9 Nov
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
A modern building with a flat roof, large windows, and a concrete facade.

10. Modern cottage centrally located with private access to the Rogue River!

Modern cottage centrally located with private access to the Rogue River!
Grants Pass
10.0 out of 10, Exceptional, (3 reviews)
"The place was perfect for a week stay"
United States
Michael
The price is AU$294
includes taxes & fees
3 Nov - 4 Nov
Modern cottage centrally located with private access to the Rogue River!
A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

11. Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (71 reviews)
"We’ve stayed in Vrbo’s around the world and this is by far our favorite."
United States
Robert B.
The price is AU$366
includes taxes & fees
3 Nov - 4 Nov
Historic Bradshaw House!
A green house with a porch, a small deck, and a view of a lake.

12. 'crater Lake' Williamson River Resort Cabin 6

'crater Lake' Williamson River Resort Cabin 6
3.0 star property
Chiloquin
10.0 out of 10, Exceptional, (1 review)
"Very nice cabin. We were able to relax and rest. Sitting on the river watching the birds, SO MANY different kinds of birds. It was nice to not have to haul utensils, pots and pans or bedding and towels. It was all ready there. Our dogs went swimming in the river and loved it. Close to Crater Lake, we took a day trip. Clean, quiet, restful. We'll be back."
United States
Brooke
The price is AU$377
includes taxes & fees
3 Nov - 4 Nov
'crater Lake' Williamson River Resort Cabin 6
A bedroom with a fireplace, a bed with a headboard, a window, and a wall-mounted picture.

13. Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.

Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
Jacksonville
9.6 out of 10, Exceptional, (4 reviews)
"Excellent location. The house was comfortable and had everything we needed."
United States
Christopher
The price is AU$366
includes taxes & fees
3 Nov - 4 Nov
Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
A blue house with a patio, a small table and chairs, and a hanging flower basket.

14. Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Central Point
9.6 out of 10, Exceptional, (40 reviews)
"Lovely cottage with all the amenities in the countryside with beautiful views down a quiet lane. Perfect for our stay to visit Jacksonville and easy access to Medford airport."
United States
Vanessa C.
The price is AU$350
includes taxes & fees
5 Nov - 6 Nov
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
A small house with a porch, a bench, and a tree with white blossoms.

15. Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Jacksonville
9.8 out of 10, Exceptional, (38 reviews)
"What a great location! We mostly sat by the river and enjoyed the scenery!"
United States
Christina B.
The price is AU$310
includes taxes & fees
19 Nov - 20 Nov
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A hot tub with a wooden bench and a table, surrounded by a railing, overlooking a river and hilly landscape.

16. 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!

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!
Gold Hill
9.8 out of 10, Exceptional, (28 reviews)
"Great accommodations, excellent communication. We all had a great time!"
United States
Sabrina D.
The price is AU$310
includes taxes & fees
7 Nov - 8 Nov
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!
A two-story house with a front porch, a covered entryway, and a small front yard.

17. Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.

Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Jacksonville Historic District
9.8 out of 10, Exceptional, (85 reviews)
"We had an awesome time!"
United States
Dena C.
The price is AU$387
includes taxes & fees
3 Nov - 4 Nov
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

18. HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (51 reviews)
"The home is a lovely older home and is located in a quiet neighborhood."
United States
Kathy L.
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
A house with a stone pathway, white picket fence, and a small porch.

19. Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.2 out of 10, Wonderful, (9 reviews)
"Location and interior was superb"
United States
Jonathan B.
The price is AU$366
includes taxes & fees
3 Nov - 4 Nov
Charming 1BR Cottage – Walk to Britt Gardens
A two-story house with a sloped roof, multiple windows, and a well-maintained garden.

20. Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.

Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget friendly.
Central Point
9.0 out of 10, Wonderful, (7 reviews)
"So easy to get in and out. Convenient to everything we did in the valley. Exactly as advertised. Great views and quiet location. Will definitely book again when in town. "
United States
Marc A.
The price is AU$407
includes taxes & fees
18 Nov - 19 Nov
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville. Charm, convenience & budget 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 Southern Oregon Hotel Reviews

Best Western Windsor Inn

Best Western Windsor Inn

10/10 Excellent
"Just spent the night after a play but enjoyed the clean room, friendly staff and nice breakfast. Pool and hot tub looked great but we didn’t have time to enjoy it."
Fred 1-night trip
Posted 1 hour ago
Best Western Windsor Inn

Find out more about Southern Oregon

Southern Oregon Cottages information

Number of reviews
811
Accommodation
195 Cottages
Lowest Price
AU$242
Highest Price
AU$578

Frequently asked questions

How much do cottages in Southern Oregon cost?
Cottages in Southern Oregon range between AU$242 and AU$578 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 195 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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