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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$433 nightly
The price is $439
Oct 5 - Oct 6
Total with taxes and fees
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
$205 nightly
The price is $224
Oct 4 - Oct 5
Total with taxes and fees
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, (238 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
$258 nightly
The price is $288
Oct 18 - Oct 19
Total with taxes and fees
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.
$158 nightly
The price is $178
Oct 4 - Oct 5
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A house with a driveway, a tree in the front yard, and a rainbow in the background.

5. Charming well appointed Cottage in Ashland ( 800 + sq. ft. )

Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Ashland
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
$240 nightly
The price is $244
Oct 4 - Oct 5
Total with taxes and fees
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

6. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (74 reviews)
"Great location in the heart of downtown"
United States
John B.
$230 nightly
The price is $257
Oct 5 - Oct 6
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
A house with a yellow front door, a blue door, and a garden with various flowers and plants.

7. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (51 reviews)
"Good location and comfy beds!"
United States
Melissa L.
$204 nightly
The price is $230
Nov 1 - Nov 2
Total with taxes and fees
Downtown Mint
A residential house with a garage, a satellite dish, and a driveway.

8. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
$206 nightly
The price is $230
Oct 5 - Oct 6
Total with taxes and fees
Charming carriage house in Ashland near downtown
A blue house with a patio, a small table and chairs, and a hanging flower basket.

9. 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, (39 reviews)
"Sweet little place that was very clean. Owners were pretty much no contact which for us was nice, I'm sure it would have been different if there was an issue. The bridge you cross right after the gate was a bit scary to cross with your vehicle but it held up fine with two vehicles."
United States
Amanda
$260 nightly
The price is $264
Nov 2 - Nov 3
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

10. 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)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
$194 nightly
The price is $196
Oct 12 - Oct 13
Total with taxes and fees
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
A modern building with a flat roof, large windows, and a concrete facade.

11. 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
$214 nightly
The price is $217
Oct 4 - Oct 5
Total with taxes and fees
Modern cottage centrally located with private access to the Rogue River!
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
$310 nightly
The price is $339
Oct 3 - Oct 4
Total with taxes and fees
'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
$270 nightly
The price is $291
Oct 28 - Oct 29
Total with taxes and fees
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 bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

14. 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.
$171 nightly
The price is $195
Oct 14 - Oct 15
Total with taxes and fees
Rosewood Studio | Private Cottage Near Downtown
A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

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

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (48 reviews)
"Amazing location and the interior design was fabulous! Has everything you need and my dog had a great time too! All around awesome place, would highly recommend."
United States
Houda
$235 nightly
The price is $264
Oct 4 - Oct 5
Total with taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

16. Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (70 reviews)
"We’ve stayed in Vrbo’s around the world and this is by far our favorite."
United States
Robert B.
$269 nightly
The price is $289
Nov 2 - Nov 3
Total with taxes and fees
Historic Bradshaw House!
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)
"What an adorable cottage. It’s right in town but on a quiet street. It had every amenity that we needed. I would very highly recommend and would stay here again"
United States
Richard
$304 nightly
The price is $322
Oct 5 - Oct 6
Total with taxes and fees
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 small house with a porch, a bench, and a tree with white blossoms.

18. 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, (37 reviews)
"Perfect spot for a solo traveler or a couple. Well-appointed and the property amenities were a nice touch."
United States
Nikki F.
$227 nightly
The price is $230
Nov 2 - Nov 3
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A house with a window, a wooden fence, and a sign reading '160 C Street'.

19. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
Fireside Cottage in Downtown Jacksonville
A hot tub with a wooden bench and a table, surrounded by a railing, overlooking a river and hilly landscape.

20. 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, (27 reviews)
"Great accommodations, excellent communication. We all had a great time!"
United States
Sabrina D.
$233 nightly
The price is $237
Oct 7 - Oct 8
Total with taxes and fees
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!
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

Cerulean Hotel

Cerulean Hotel

8/10 Good
"comfortable stay, have a breakfast at waffle depot"
HARRY 1-night trip
Posted 3 hours ago
Cerulean Hotel

Find out more about Southern Oregon

Southern Oregon Cottages information

Number of reviews
814
Accommodation
204 Cottages
Lowest Price
$178
Highest Price
$439

Frequently asked questions

How much do cottages in Southern Oregon cost?
You'll pay between $178 and $439 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 9.8. 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 204 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.
Are there any family-friendly cottages in Southern Oregon?
You'll discover some very comfortable family-friendly cottages in Southern Oregon. If you're seeking a slower pace in Medford, make a reservation at Rellik House. Winery And Alpaca Farm. With amenities such as WiFi and a fireplace, your entire crew will feel relaxed and comfy at this 3.5-star property. Wine Suite At Rellik House. Winery And Alpaca Farm is another popular choice for families in Medford. This 3.5-star cottage includes WiFi, a firepit and more. You'll find plenty of fun things to do for the whole family in Medford. Roxy Ann Peak and Prescott Park and Rogue Valley Family Fun Center deliver a wonderful day out.
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.
What is there to do in Southern Oregon near my cottage?
One of the most important travel accessories for your Southern Oregon trip is a good itinerary! Fichtner-Mainwaring Park, Rogue Valley Country Club and Bear Creek Park are among the well-known sights if you're making your way to Medford. Ashland is also packed with excellent attractions, such as ScienceWorks Hands-On Museum. In the mood to explore more? Visit North Mountain Park and Angus Bowmer Theatre too.

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