Search Cottages in Southern Oregon

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Our top choices for Southern Oregon cottages

3.0 star property
The price is AED 305
AED 775 total
includes taxes & fees
5 Jan - 6 Jan
Family-friendly 1BR w/ Laundry: Dogs Welcome

Cottage in Talent

Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (15)
"Great space and beautiful views. 10/10 experience. "
United States
Cody
The price is AED 422
AED 778 total
includes taxes & fees
3 Feb - 4 Feb
Paschal Winery
9.8 out of 10, Exceptional, (102)
"The stay was private and great "
United States
bradley s.
The price is AED 287
AED 567 total
includes taxes & fees
5 Jan - 6 Jan
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.2 out of 10, Wonderful, (17)
"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 AED 432
AED 807 total
includes taxes & fees
5 Jan - 6 Jan
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
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 AED 364
AED 611 total
includes taxes & fees
5 Jan - 6 Jan
The Vintage Cottage with riverfront access
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 AED 422
AED 794 total
includes taxes & fees
7 Jan - 8 Jan
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
9.8 out of 10, Exceptional, (32)
"Absolutely awesome place for a cute girls night! Loved all the animals. Just what we were looking for ."
United States
Natalie K.
The price is AED 441
AED 794 total
includes taxes & fees
5 Jan - 6 Jan
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
10.0 out of 10, Exceptional, (22)
"We had an incredible stay at this serene riverside retreat along the Rogue River. The home was spotless, well-equipped, and thoughtfully maintained—everything we needed for a comfortable getaway. Although a nearby wildfire caused a brief power outage, it didn’t dampen our experience. The host was communicative and gracious throughout, and the location is perfect for exploring Crater Lake National Park and the surrounding natural beauty. We’d gladly return for another visit!"
United States
Vishnu
The price is AED 472
AED 769 total
includes taxes & fees
5 Jan - 6 Jan
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 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.
The price is AED 422
AED 811 total
includes taxes & fees
31 Jan - 1 Feb
Charming carriage house in Ashland near downtown
9.8 out of 10, Exceptional, (26)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
The price is AED 459
AED 843 total
includes taxes & fees
14 Jan - 15 Jan
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
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 AED 316
AED 697 total
includes taxes & fees
5 Jan - 6 Jan
On-site Winery & Tasting Room: Oregon Bungalow!
9.6 out of 10, Exceptional, (22)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is AED 426
AED 872 total
includes taxes & fees
5 Jan - 6 Jan
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
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 AED 525
AED 1,116 total
includes taxes & fees
13 Jan - 14 Jan
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
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 AED 446
AED 718 total
includes taxes & fees
10 Jan - 11 Jan
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (60)
"Very clean, great location. Well appointed . Loved it and would definitely come back. "
United States
Dawn
The price is AED 452
AED 926 total
includes taxes & fees
27 Jan - 28 Jan
Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (10)
"Nice guest house. Comfortable bed and furniture, well stocked kitchen. The host her family and dogs were friendly.Would stay again. "
United States
Thomas M.
The price is AED 496
AED 884 total
includes taxes & fees
15 Jan - 16 Jan
Diamond D Fully Furnished 1 Bedroom Guest House
8.0 out of 10, Very Good, (1)
"Location was as advertised."
United States
william L.
The price is AED 440
AED 762 total
includes taxes & fees
5 Jan - 6 Jan
Rosewood Studio | Private Cottage Near Downtown

Cottage in Siskiyou-Hargadine Historic District

The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (211)
"Great location and comfortable accommodations. This is our second time staying here."
United States
Kathleen P.
The price is AED 613
AED 1,048 total
includes taxes & fees
5 Jan - 6 Jan
The Ashland Cottage, walk to town
10.0 out of 10, Exceptional, (1)
"The house was so cute not far from town and had access to the Rogue river. The owner had a hand written welcome note along with fresh flowers to greet us as we arrived. The house was well equipped with all the necessities of home including snacks, water bottles, coffee, shampoo, conditioner, laundry soap, pots and pans and comfy beds with lovely linens. We couldn’t ask for a better introduction to the beautiful state of Oregon and the town of Grants Pass. Thank you!"
United States
Tamara F.
Modern cottage centrally located with private access to the Rogue River!
8.0 out of 10, Very Good, (1)
"The House was well setup and Very Clean. The check-in process and getting the Codes to the property was not explained in the Rental process and it was last minute. "
United States
George L.
The price is AED 404
AED 934 total
includes taxes & fees
5 Jan - 6 Jan
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

Frequently asked questions

How much do cottages in Southern Oregon cost?
You'll pay between AED 567 and AED 1,116 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 9.6. 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 198 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.