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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)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
$177 nightly
The price is $180
Nov 30 - Dec 1
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
Dec 11 - Dec 12
Total with taxes and fees
Charming carriage house in Ashland near downtown
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, (59)
"Great Location and Comfortable Unit."
United States
John V.
$189 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Exterior
The Ashland Cottage, walk to town

The Ashland Cottage, walk to town

Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (210)
"Great place for a couple. Nice house. Good location."
United States
Tamara H.
$243 nightly
The price is $271
Nov 30 - Dec 1
Total with taxes and fees
The Ashland Cottage, walk to town
Outdoor dining
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
$483 nightly
The price is $538
Nov 30 - Dec 1
Total with taxes and fees
Railroad District, steps to downtown, everything you need to enjoy Ashland!
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, (5)
$335 nightly
The price is $373
Nov 30 - Dec 1
Total with taxes and fees
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
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
9.6 out of 10, Exceptional, (19)
"We loved "
United States
Phyllis M.
$335 nightly
The price is $373
Dec 1 - Dec 2
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, (14)
"Very nice and hassle free check in "
United States
Matthew
$206 nightly
The price is $209
Dec 29 - Dec 30
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)
"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
Nov 30 - Dec 1
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)
"I travel to Central Point regularly, and this was my second stay at this lovely gem. I'll be back again. Clean, bright, and comfortable. "
United States
Mike W.
$157 nightly
The price is $177
Nov 30 - Dec 1
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
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)
"We loved the animals and how peaceful it was there,The owner was very accommodating and nice. Highly recommend if I ever need to stay in the area again this would be my first pick "
United States
Ryan K.
$215 nightly
The price is $218
Nov 29 - Nov 30
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior
Downtown Mint

Downtown Mint

Medford
9.8 out of 10, Exceptional, (40)
"Loved the house, had a great stay!"
United States
Kara B.
$193 nightly
The price is $217
Dec 8 - Dec 9
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, (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.
$188 nightly
The price is $191
Dec 5 - Dec 6
Total with taxes and fees
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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, (26)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
$229 nightly
The price is $232
Dec 1 - Dec 2
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
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 property everything we needed close to town perfect stay!"
United States
Chuck F.
$212 nightly
The price is $239
Nov 30 - Dec 1
Total with taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
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
Dec 15 - Dec 16
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
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils
Rosewood Studio | Private Cottage Near Downtown

Rosewood Studio | Private Cottage Near Downtown

Medford
$181 nightly
The price is $204
Nov 29 - Nov 30
Total with taxes and fees
Rosewood Studio | Private Cottage Near Downtown
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)
"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.
$205 nightly
The price is $208
Nov 30 - Dec 1
Total with taxes and fees
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
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, (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.
$278 nightly
The price is $307
Dec 5 - Dec 6
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

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.
$301 nightly
The price is $332
Nov 30 - Dec 1
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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Top Ashland Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"Nice staff"
max 1-night trip
Posted 2 days ago
Stratford Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
570
Accommodation
127 Cottages
Lowest Price
$177
Highest Price
$538

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between $177 and $538 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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