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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Ashland cottages

A residential house with a garage, a satellite dish, and a driveway.

1. Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
10.0 out of 10, Exceptional, (13 reviews)
"Lovely stay. "
United States
Cyndy K.
$207 nightly
The price is $231
Sep 28 - Sep 29
Total with taxes and fees
Charming carriage house in Ashland near downtown
A house with a driveway, a tree in the front yard, and a rainbow in the background.

2. 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, (19 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
$240 nightly
The price is $244
Sep 29 - Sep 30
Total with taxes and fees
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
A house with a wooden deck, a stone wall, and a wooden fence.

3. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (237 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
$258 nightly
The price is $288
Oct 18 - Oct 19
Total with taxes and fees
The Ashland Cottage, walk to town
A modern living room with a grey sofa, a small table, and a basket on a white ottoman.

4. Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (73 reviews)
"Great location in the heart of downtown"
United States
John B.
$252 nightly
The price is $281
Oct 5 - Oct 6
Total with taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
An outdoor patio with a grill, dining table, chairs, and string lights.

5. Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (19 reviews)
"Stunning scenery, great wine and food. Friendly, helpful people on site and the hot tub is blissfully perfect ❤️"
United States
Christine
$431 nightly
The price is $438
Oct 5 - Oct 6
Total with taxes and fees
Paschal Winery
A house with a yellow front door, a blue door, and a garden with various flowers and plants.

6. Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (51 reviews)
"Good location and comfy beds!"
United States
Melissa L.
$214 nightly
The price is $241
Sep 24 - Sep 25
Total with taxes and fees
Downtown Mint

7. 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, (128 reviews)
"We had such an amazing relaxing weekend at this little hidden jewel, tucked away in Central Point. "
United States
Chris A.
$148 nightly
The price is $167
Sep 24 - Sep 25
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A bedroom with a bed, a TV, a ladder, a mirror, a basket, and a door with a 'No Smoking' sign.

8. Rosewood Studio | Private Cottage Near Downtown

Rosewood Studio | Private Cottage Near Downtown
Medford
8.0 out of 10, Very good, (1 review)
"Location was as advertised."
United States
william L.
$171 nightly
The price is $195
Sep 28 - Sep 29
Total with taxes and fees
Rosewood Studio | Private Cottage Near Downtown
A single-story house with a gabled roof, surrounded by a variety of plants and shrubs.

9. HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.6 out of 10, Exceptional, (48 reviews)
"Amazing location and the interior design was fabulous! Has everything you need and my dog had a great time too! All around awesome place, would highly recommend."
United States
Houda
$229 nightly
The price is $258
Sep 30 - Oct 1
Total with taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
A residential house with a front porch, a small garden with various plants and flowers, and a gravel driveway.

10. 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, (18 reviews)
"Everything was wonderful Will definitely stay again"
United States
Kellie P.
$192 nightly
The price is $194
Oct 5 - Oct 6
Total with taxes and fees
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
A blue house with a patio, a small table and chairs, and a hanging flower basket.

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

Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Central Point
9.6 out of 10, Exceptional, (39 reviews)
"Sweet little place that was very clean. Owners were pretty much no contact which for us was nice, I'm sure it would have been different if there was an issue. The bridge you cross right after the gate was a bit scary to cross with your vehicle but it held up fine with two vehicles."
United States
Amanda
$259 nightly
The price is $263
Sep 29 - Sep 30
Total with taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
A small, single-story house with a white picket fence, a purple front door, and a porch with white railings.

12. Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (70 reviews)
"Great highly recommend"
United States
Linda J.
$281 nightly
The price is $303
Oct 4 - Oct 5
Total with taxes and fees
Historic Bradshaw House!
A house with a stone pathway, white picket fence, and a small porch.

13. Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.2 out of 10, Wonderful, (9 reviews)
"Stayed here for our anniversary. We loved the room and able to walk across the street to shop, eat and have drinks. So convenient. Easy to book and access. Loved the tub. Great hosts."
United States
Tami&
$270 nightly
The price is $291
Sep 24 - Sep 25
Total with taxes and fees
Charming 1BR Cottage – Walk to Britt Gardens
A two-story house with a front porch, a covered entryway, and a small front yard.

14. Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.

Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Jacksonville Historic District
9.8 out of 10, Exceptional, (85 reviews)
"What an adorable cottage. It’s right in town but on a quiet street. It had every amenity that we needed. I would very highly recommend and would stay here again"
United States
Richard
$304 nightly
The price is $322
Sep 28 - Sep 29
Total with taxes and fees
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
A small house with a porch, a bench, and a tree with white blossoms.

15. 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, (37 reviews)
"Perfect spot for a solo traveler or a couple. Well-appointed and the property amenities were a nice touch."
United States
Nikki F.
$230 nightly
The price is $233
Oct 7 - Oct 8
Total with taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
A bedroom with a fireplace, a bed with a headboard, a window, and a wall-mounted picture.

16. Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.

Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
Jacksonville
9.6 out of 10, Exceptional, (4 reviews)
"Very nice place all interior updated the only minus was lack of any outside patio area . Location is outstanding"
United States
linda s.
$271 nightly
The price is $292
Oct 21 - Oct 22
Total with taxes and fees
Walk to the Britt Festival and downtown Jacksonville from this newly remodeled luxury cottage. Features a king bed with luxury linens, dramatic centerpiece fireplace, pull-out sofa, full kitchen, and spa-style bathroom.
A residential property with a paved driveway leading to a front door, a wooden fence, and a small garden area.

17. 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, (2 reviews)
"Wonderful place and great location"
United States
darren t.
$355 nightly
The price is $393
Sep 30 - Oct 1
Total with taxes and fees
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
A two-story house with a sloped roof, multiple windows, and a well-maintained garden.

18. 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.

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.
Central Point
9.0 out of 10, Wonderful, (7 reviews)
"So easy to get in and out. Convenient to everything we did in the valley. Exactly as advertised. Great views and quiet location. Will definitely book again when in town. "
United States
Marc A.
$302 nightly
The price is $324
Oct 15 - Oct 16
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.
A house with a window, a wooden fence, and a sign reading '160 C Street'.

19. Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
$226 nightly
The price is $253
Sep 28 - Sep 29
Total with taxes and fees
Fireside Cottage in Downtown Jacksonville
A cabin with a stone exterior, a porch with a red door, and a sign reading "The Cottage."

20. Forest Cabin by Crater Lake & Klamath Falls

Forest Cabin by Crater Lake & Klamath Falls
3.0 star property
Klamath Falls
10.0 out of 10, Exceptional, (1 review)
"Super chalet dans la forêt très bien équipé, cadre très agréable, logement charmant. Juste bien penser a faire des courses avant l’arrivee"
France
Murielle
$205 nightly
The price is $224
Oct 4 - Oct 5
Total with taxes and fees
Forest Cabin by Crater Lake & Klamath Falls
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

8/10 Good
"I booked this hotel largely because the cleanliness rating was 9.4, so unfortunately I was disappointed that the actual cleanliness did not live up to those expectations. The floors were quite dirty, with noticeable debris buildup in the corners. The sheets, comforter, and mattress pad were also stained, worn, and in some areas starting to tear. These are things I would expect to be addressed, especially given the hotel’s high cleanliness rating. That said, one of the biggest positives was the lovely woman working the breakfast area. She was genuinely one of the sweetest people I’ve encountered during a hotel stay. She was incredibly warm and attentive, asked guests about their stays, and remembered people as they came back for breakfast. You could tell her kindness was completely genuine. She truly was a gem and made the breakfast experience feel special. Overall, I think the hotel has some room for improvement when it comes to housekeeping and the condition of the bedding, but the wonderful woman working breakfast was an absolute bright spot during our stay."
Tessa 2-night trip
Posted 5 hours ago
Stratford Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
696
Accommodation
126 Cottages
Lowest Price
$167
Highest Price
$438

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between $167 and $438 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 126 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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