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Cottages in Southern Oregon

Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (13)
"It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland."
United States
Heidi
$177 nightly
The price is $180
Nov 17 - Nov 18
Total with taxes and fees
Paschal Winery
On-site Winery & Tasting Room: Oregon Bungalow!
3.0 star property
8.4 out of 10, Very Good, (5)
"Was A nice oasis deer came and visited me in the morning, and the view was outstanding!"
United States
Samona
$211 nightly
The price is $214
Nov 8 - Nov 9
Total with taxes and fees
On-site Winery & Tasting Room: Oregon Bungalow!
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.8 out of 10, Exceptional, (100)
"This is a really great spot to stay. I was attending a wedding in Central pPoint. Lots of wineries close by, hiking trails, and of course you can get into town pretty easily. Beautiful spots to enjoy the river are within minutes. There’s even a couple stores and restaurants that you can walk to. I would definitely stay here again."
United States
Michelle H.
$156 nightly
The price is $176
Nov 9 - Nov 10
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
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
9.4 out of 10, Exceptional, (16)
"Peaceful location on the river."
United States
John H.
$216 nightly
The price is $216
Nov 10 - Nov 11
Total with taxes and fees
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
Charming carriage house in Ashland near downtown
10.0 out of 10, Exceptional, (6)
"Enjoyed our stay"
United States
Julie M.
$186 nightly
The price is $207
Nov 17 - Nov 18
Total with taxes and fees
Charming carriage house in Ashland near downtown
The Vintage Cottage with riverfront access
9.8 out of 10, Exceptional, (109)
"Really enjoyed my stay here. Teresa and her pups are very welcoming! Highly recommended!"
United States
Joanne T.
$164 nightly
The price is $166
Nov 10 - Nov 11
Total with taxes and fees
The Vintage Cottage with riverfront access
Downtown Mint
9.8 out of 10, Exceptional, (39)
"We had a wonderful stay at Downtown Mint. The house was as advertised. The property was clean and the beds were comfortable."
United States
Carrie J.
$180 nightly
The price is $203
Nov 11 - Nov 12
Total with taxes and fees
Downtown Mint
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
9.8 out of 10, Exceptional, (32)
"The cottage was the perfect little place to retreat after wine tasting and walking around Jacksonville. Just far enough out and amongst wineries but still close to downtown :) lovely outdoor space with a relaxing river front seating. We just loved it!"
United States
Kelseyann R.
$215 nightly
The price is $218
Nov 7 - Nov 8
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
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!
10.0 out of 10, Exceptional, (22)
"We enjoyed our stay very much my husband was very happy we got to barbecue and celebrate a day late for Father's day but it was worth the wait we enjoyed the hot tub The view the whole visit was great thank you so much"
United States
Mike B.
$205 nightly
The price is $206
Nov 7 - Nov 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!
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
9.8 out of 10, Exceptional, (25)
"This house was a awesome cute little place! Definitely recommend if you have pets the fenced in yard was nice! 😊"
United States
Maiah C.
$226 nightly
The price is $229
Nov 7 - Nov 8
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
10.0 out of 10, Exceptional, (18)
"Nice place. Very clean and well appointed. Close to town, but still on a farm that makes it seem far away. We'd come back."
United States
Dan W.
$176 nightly
The price is $179
Nov 16 - Nov 17
Total with taxes and fees
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Fish & Hike: Peaceful Cabin on Williamson River
3.0 star property
$335 nightly
The price is $366
Nov 8 - Nov 9
Total with taxes and fees
Fish & Hike: Peaceful Cabin on Williamson River
Wildlife Preserve, Country Cottage, Spacious
8.4 out of 10, Very Good, (22)
"It was quiet and peaceful. I loved seeing the wildlife. The cottage was comfortable and would be perfect for a family with small kids."
United States
christine
$155 nightly
The price is $157
Nov 8 - Nov 9
Total with taxes and fees
Wildlife Preserve, Country Cottage, Spacious
Historic Home in Klamath Falls
9.6 out of 10, Exceptional, (19)
"This is a comfortable little house in a good location for exploring the Klamath Basin area. The neighborhood is generally quiet and the house is convenient to downtown."
United States
Charles H.
$335 nightly
The price is $367
Nov 28 - Nov 29
Total with taxes and fees
Historic Home in Klamath Falls
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
9.6 out of 10, Exceptional, (22)
"Great location Clean cute cottage with everything we needed for our stay. Would definitely stay again"
United States
Jim Z.
$203 nightly
The price is $228
Nov 10 - Nov 11
Total with taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (58)
"The place is exactly as pictured and extremely comfortable. It is such a great neighborhood with easy walks to restaurants and plays. "
United States
Kim C.
$208 nightly
The price is $232
Nov 18 - Nov 19
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
10.0 out of 10, Exceptional, (2)
"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.
$187 nightly
The price is $190
Nov 13 - Nov 14
Total with taxes and fees
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Modern cottage centrally located with private access to the Rogue River!
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.
$212 nightly
The price is $215
Nov 12 - Nov 13
Total with taxes and fees
Modern cottage centrally located with private access to the Rogue River!
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
10.0 out of 10, Exceptional, (44)
"We had the most lovely stay in Jacksonville for a quick weekend getaway to celebrate my sister‘s 50th birthday! The property is beautifully Appointed and has everything you need for a comfortable and luxurious getaway! The bed was plush and inviting, and we had plenty of room for our small group to lounge, make snacks, enjoy a glass of wine, and have wonderful conversations! We will definitely visit again! "
United States
amzncali B.
$319 nightly
The price is $353
Nov 16 - Nov 17
Total with taxes and fees
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
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.
$325 nightly
The price is $359
Nov 7 - Nov 8
Total with taxes and fees
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
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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Frequently asked questions

How much do cottages in Southern Oregon cost?
You'll pay between and 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 . 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 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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