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 SAR 466
SAR 1,531 total
includes taxes & fees
4 Nov - 5 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 SAR 447
SAR 841 total
includes taxes & fees
3 Nov - 4 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 SAR 627
SAR 1,063 total
includes taxes & fees
2 Dec - 3 Dec
The Ashland Cottage, walk to town
Exterior

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 SAR 368
SAR 633 total
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.
Charming carriage house in Ashland near downtown
A house with a yellow front door, a blue door, and a garden with various flowers and plants.

6. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (52 reviews)
"Good location and comfy beds!"
United States
Melissa L.
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.
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 SAR 510
SAR 766 total
includes taxes & fees
1 Dec - 2 Dec
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
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 SAR 432
SAR 975 total
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 SAR 679
SAR 995 total
includes taxes & fees
12 Nov - 13 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 SAR 531
SAR 1,098 total
includes taxes & fees
15 Nov - 16 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.
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 SAR 477
SAR 811 total
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 SAR 557
SAR 816 total
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.
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.
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 SAR 527
SAR 1,143 total
includes taxes & fees
2 Dec - 3 Dec
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 less than an hour ago
Best Western Windsor Inn

Frequently asked questions

How much do cottages in Southern Oregon cost?
You'll pay between SAR 633 and SAR 1,531 per night for cottages in Southern Oregon. Whatever your budget, an awesome stay is only a click away on Expedia. These prices were 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.
What are the best cottages in Southern Oregon?
Southern Oregon has multiple cottages with a total average guest review rating of 9.7. Planning a getaway to Medford? Travelers prefer Rellik House. Winery And Alpaca Farm, a 3.5-star option with a swimming pool and a fireplace. Another popular pick where you can get away from the routine is Wine Suite At Rellik House. Winery And Alpaca Farm. It has a 3.5-star rating and amenities such as an attached winery and a garden.
How many cottages are there in Southern Oregon?
Look up our 195 cottages in Southern Oregon and then select your favorite. Whether you're dreaming of a family vacay or a weekend with besties, your ideal stay is just clicks away with Expedia.
Why book your cottage in Southern Oregon with Expedia?
We think that a vacay should be stress-free, so if you're chasing cottages in Southern Oregon at a competitive price, Expedia is here to help. Keep the budget in check and go for a low-cost option far from the rush of the city, or book a 5-star cottage to really pamper your favorite people.
How can I find cheap cottages in Southern Oregon?
A good way to locate cheap cottages in Southern Oregon is with Expedia's useful filter tool. Refine your search results by star rating, budget and amenities to land awesome rates in a few clicks.