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Our top choices for Ashland cottages

Property grounds
Charming carriage house in Ashland near downtown

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.
$186 nightly
The price is $207
Dec 31 - Jan 1, 2026
Total with taxes and fees
Charming carriage house in Ashland near downtown
Fridge, microwave, coffee/tea maker, toaster
Courtside Cottage - WalkScore 93 - Dog Friendly

Cottage in Historic Railroad District

Courtside Cottage - WalkScore 93 - Dog Friendly
10.0 out of 10, Exceptional, (59)
"Great stay. Loved the location and the host was super great. "
United States
Aaron B.
$211 nightly
The price is $236
Jan 8 - Jan 9, 2026
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Exterior
The Ashland Cottage, walk to town

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.
$261 nightly
The price is $291
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Ashland Cottage, walk to town
Property grounds
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

Cottage in Historic Railroad District

Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
9.6 out of 10, Exceptional, (19)
"We loved "
United States
Phyllis M.
$335 nightly
The price is $373
Dec 25 - Dec 26
Total with taxes and fees
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Terrace/patio
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

Cottage in Historic Railroad District

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
10.0 out of 10, Exceptional, (5)
"Great location, many personal touches and the host cares about comfort! Will stay again, thanks so much! "
United States
Krista M.
$336 nightly
The price is $374
Jan 4 - Jan 5, 2026
Total with taxes and fees
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Cottage (1 Bedroom) | Interior
On-site Winery & Tasting Room: Oregon Bungalow!

Cottage in Central Point

On-site Winery & Tasting Room: Oregon Bungalow!
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
$217 nightly
The price is $220
Dec 24 - Dec 25
Total with taxes and fees
On-site Winery & Tasting Room: Oregon Bungalow!
Glamp Cottage Trailer | Terrace/patio
Paschal Winery

Cottage in Talent

Paschal Winery
4.5 star property
9.6 out of 10, Exceptional, (15)
"Very nice and hassle free check in "
United States
Matthew
$221 nightly
The price is $224
Jan 21 - Jan 22, 2026
Total with taxes and fees
Paschal Winery
Exterior
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Cottage in Central Point

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
9.8 out of 10, Exceptional, (102)
"Super cute place! Perfectly located in the middle of things. Food and drink near by."
United States
Rachel B.
$143 nightly
The price is $161
Jan 1 - Jan 2, 2026
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville

Cottage in Central Point

Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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.
$187 nightly
The price is $190
Dec 31 - Jan 1, 2026
Total with taxes and fees
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

Cottage in City Center Medford

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
9.6 out of 10, Exceptional, (22)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
$209 nightly
The price is $235
Dec 24 - Dec 25
Total with taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Exterior
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

Cottage in Jacksonville

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
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.
$215 nightly
The price is $218
Dec 24 - Dec 25
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils
Rosewood Studio | Private Cottage Near Downtown

Cottage in Medford

Rosewood Studio | Private Cottage Near Downtown
8.0 out of 10, Very Good, (1)
"Location was as advertised."
United States
william L.
$185 nightly
The price is $209
Dec 30 - Dec 31
Total with taxes and fees
Rosewood Studio | Private Cottage Near Downtown
Terrace/patio
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Cottage in Central Point

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
9.8 out of 10, Exceptional, (26)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
$227 nightly
The price is $230
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains

Cottage in Central Point

🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
8.8 out of 10, Excellent, (9)
"This place was amazing. Took a little extra time to get to, but it was well worth it. Would definitely stay here again. Thanks again for all necessary accommodations as well. Definitely appreciated 🙏"
United States
Silent Tunez P.
$204 nightly
The price is $207
Dec 29 - Dec 30
Total with taxes and fees
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
Exterior
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.

Cottage in Central Point

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.
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.
$238 nightly
The price is $255
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
Exterior
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Cottage in Jacksonville Historic District

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
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.
$274 nightly
The price is $303
Dec 31 - Jan 1, 2026
Total with taxes and fees
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
Exterior
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

Cottage in Jacksonville Historic District

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.
$340 nightly
The price is $375
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience

Cottage in Central Point

Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
$400 nightly
The price is $429
Jan 6 - Jan 7, 2026
Total with taxes and fees
Wake to breathtaking sunrises over the rolling hills! Relax by the fire under the stars, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience
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 Ashland Hotel Reviews

Callahan's Mountain Lodge

Callahan's Mountain Lodge

10/10 Excellent
"The staff was amazing, very kind and helpful. The lodge has little details that make it worthwhile, such as a full drink station right when you walk in and free unlimited firewood. It's a very cozy, pretty and comfortable place to stay."
Adria 2-night trip
Posted 23 hours ago
Callahan's Mountain Lodge

Find out more about Ashland

Ashland Cottages information

Number of reviews
524
Accommodation
129 Cottages
Lowest Price
$161
Highest Price
$429

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between $161 and $429 per night. These properties offer a chance to get in touch with nature — at a price you can afford. 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 Ashland?
Ashland has multiple cottages with a total average guest review rating of 9.6. Oak Street Cottages is a good option if you're into nature and an easy-breezy pace. Guests of this 3-star stay will enjoy amenities such as a fireplace and a barbecue grill. The Retreat At Oak Knoll ~ Pet Friendly is another popular pick. This 4-star cottage features a fireplace and a barbecue grill.
How many cottages are there in Ashland?
Pack your suitcase and pick from 129 cottages in Ashland. Longing for a place where you can relax and connect with nature? Expedia will help you find your ideal retreat in only a click or two.
Are there any family-friendly cottages in Ashland?
A trip with the family in Ashland is a cinch at Oak Street Cottages. With conveniences including a barbecue grill and a picnic area, you'll have all the comforts of home at this 3-star cottage. The Retreat At Oak Knoll ~ Pet Friendly is another family-friendly stay where you and your crew can escape the daily grind of the city. This cottage has a 4-star rating and amenities including a fireplace and a barbecue grill. Once you've checked in and dropped off your things, there are lots of family-friendly attractions to visit in and around Ashland. ScienceWorks Hands-On Museum and Mount Ashland Ski Area guarantee fun for young and old.
Are there any 5-star cottages in Ashland?
Ashland doesn't have any 5-star cottages — but you and the family can still enjoy a stylish getaway! Why not have a look at The Retreat At Oak Knoll ~ Pet Friendly? Located approximately 3 miles from downtown, this 4-star retreat features a living room and a garden. C' Street Station - Short Walk To Osf is another fantastic 4-star pick just 0.5 miles from central Ashland. It provides a relaxed vibe close to nature as well as conveniences like a fireplace and free WiFi.
Why book your cottage in Ashland with Expedia?
Expedia has some superb cottages in Ashland, so get set for a memorable vacation close to nature. If you have a certain budget, click on how much you want to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with a pool or free WiFi. We'll help you find the right fit whatever your style of travel or plans.
How can I find cheap cottages in Ashland?
The easiest way to track down cheap cottages in Ashland is with Expedia's convenient filter tool. Refine your search results by budget, star rating and amenities to grab unbeatable bargains in just a few clicks.
What is there to do in Ashland near my cottage?
Whatever you're interested in, Ashland has plenty to keep you entertained. Emigrant Lake, Angus Bowmer Theatre and ScienceWorks Hands-On Museum are on many visitors' sightseeing plans. Don't miss North Mountain Park, Mount Ashland Ski Area and Allen Elizabethan Theatre either. With Expedia's Ashland hotel deals, you can see more fantastic attractions like these with the cash you save.

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