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Cottages in Ashland

Exterior
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, (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. )
Property grounds
Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown

Skidmore Academy Historic District
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
Exterior
The Ashland Cottage, walk to town

The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (209)
"Great place for a couple. Nice house. Good location."
United States
Tamara H.
$260 nightly
The price is $290
Nov 11 - Nov 12
Total with taxes and fees
The Ashland Cottage, walk to town
Fridge, microwave, coffee/tea maker, toaster
Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly

Historic Railroad District
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.
$206 nightly
The price is $230
Nov 18 - Nov 19
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Terrace/patio
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!

Historic Railroad District
10.0 out of 10, Exceptional, (4)
"Very clean, large kitchen with all the tools. Really liked the wood flooring and solid doors. Great parking for us as we had 2 full sized trucks. Host was communicative and engaged. We didn't have any pets. "
United States
Kerry D.
$336 nightly
The price is $374
Nov 11 - Nov 12
Total with taxes and fees
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Fridge, microwave, oven, stovetop
Railroad District, steps to downtown, everything you need to enjoy Ashland!

Railroad District, steps to downtown, everything you need to enjoy Ashland!

2.0 star property
Historic Railroad District
$510 nightly
The price is $569
Nov 8 - Nov 9
Total with taxes and fees
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Property grounds
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

Historic Railroad District
10.0 out of 10, Exceptional, (17)
"great location and we were able to walk to everything we wanted to do in Ashland, clean unit and quiet, clear rules."
United States
Cynthia K.
$330 nightly
The price is $368
Nov 8 - Nov 9
Total with taxes and fees
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Glamp Cottage Trailer | Terrace/patio
Paschal Winery

Paschal Winery

4.5 star property
Talent
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 20 - Nov 21
Total with taxes and fees
Paschal Winery
Cottage (1 Bedroom) | Interior
On-site Winery & Tasting Room: Oregon Bungalow!

On-site Winery & Tasting Room: Oregon Bungalow!

3.0 star property
Central Point
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!
Exterior
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, (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
Terrace/patio
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Central Point
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 8 - Nov 9
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Exterior
Downtown Mint

Downtown Mint

Medford
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.
$185 nightly
The price is $208
Nov 12 - Nov 13
Total with taxes and fees
Downtown Mint
Exterior
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, (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 14 - Nov 15
Total with taxes and fees
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
Exterior
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, (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 8 - Nov 9
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

City Center Medford
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
Exterior
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains

🌻 Charming Cottage On Peaceful 5 Acres in the Mountains

Central Point
8.8 out of 10, Excellent, (9)
"My husband and I arrived at the property I reserved only to find it occupied by a month-to-month resident that was staying for the summer. The tenant was very nice and helpful, and she called the owner directly to clarify the double booking. The owner apologized and told me he had another property available and he would refund the nightly rate. We drove to the other property that was about 10 miles away. Now I am not going to review the alternate property as it is not relevant to this...
United States
Margaret H.
$204 nightly
The price is $207
Nov 8 - Nov 9
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, & savor sunset dinners beneath fragrant wisteria pergola. Surrounded by wineries and minutes from historic Jacksonville, this retreat blends charm & convenience

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

Central Point
$238 nightly
The price is $255
Nov 12 - Nov 13
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
Exterior
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville

Jacksonville Historic District
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 8 - Nov 9
Total with taxes and fees
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Jacksonville Historic District
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
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

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

Central Point
$424 nightly
The price is $454
Nov 20 - Nov 21
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

Lithia Springs Resort

Lithia Springs Resort

10/10 Excellent
"Great place. Highly recommend."
Ronald 1-night trip
Posted 16 hours ago
Lithia Springs Resort

Find out more about Ashland

Ashland Cottages information

Number of reviews
561
Accommodation
127 Cottages
Lowest Price
$176
Highest Price
$569

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between $176 and $569 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 9.7. 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 127 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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