A resident black-tail deer walks the streets of Ashland, Oregon

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Ashland cottages

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 reviews)
"Wonderful location, well appointed place very quiet, beautifully located, and very special place on the farm"
United States
Greg M.
The price is NZ$417
includes taxes & fees
15 June - 16 June
Charming well appointed Cottage in Ashland ( 800 + sq. ft. )
Property grounds

The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (225 reviews)
"Great spot, close to town, cozy and comfortable!"
United States
Carey C.
The Ashland Cottage, walk to town
Property grounds

Charming carriage house in Ashland near downtown

Charming carriage house in Ashland near downtown
Skidmore Academy Historic District
9.8 out of 10, Exceptional, (10 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is NZ$418
includes taxes & fees
22 June - 23 June
Charming carriage house in Ashland near downtown
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, (8 reviews)
"Great location, many personal touches and the host cares about comfort! Will stay again, thanks so much! "
United States
Krista M.
Delightful 2~bedroom, pet~friendly cottage~Walking distance to everything!
Smart TV, books

Courtside Cottage - WalkScore 93 - Dog Friendly

Courtside Cottage - WalkScore 93 - Dog Friendly
Historic Railroad District
10.0 out of 10, Exceptional, (63 reviews)
"Clean, comfortable and great location. We really enjoyed our stay and look forward to returning."
United States
Tonya W.
Courtside Cottage - WalkScore 93 - Dog Friendly
Dream Cottage 1 | Terrace/patio

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.8 out of 10, Exceptional, (18 reviews)
"Incredible experience, fabulous wine, wish we had stayed longer to soak in the beauty of the experience. "
United States
Frankie
The price is NZ$724
includes taxes & fees
29 June - 30 June
Paschal Winery
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, (6 reviews)
"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.
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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, (113 reviews)
"We had such an amazing relaxing weekend at this little hidden jewel, tucked away in Central Point. "
United States
Chris A.
The price is NZ$307
includes taxes & fees
1 July - 2 July
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
1 bedroom, WiFi, bed sheets

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.
The price is NZ$361
includes taxes & fees
14 June - 15 June
Rosewood Studio | Private Cottage Near Downtown
Exterior

Downtown Mint

Downtown Mint
Medford
10.0 out of 10, Exceptional, (45 reviews)
"Loved the house, had a great stay!"
United States
Kara B.
The price is NZ$374
includes taxes & fees
15 June - 16 June
Downtown Mint
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, (34 reviews)
"Knocked our socks off. Beautiful place, with animals in a green space and riverside hangouts on the Applegate. Lodgings next to the road, but that’s quiet at night and the river side is where you hang out. The host has built something special, and she’s on it all the time. She’s also more than tidy, so less is more, which some of us love. Don’t miss the tiny towns on the west, Applegate, Provolt, and Williams. They’re tiny but friendly."
United States
Edmond
The price is NZ$463
includes taxes & fees
16 June - 17 June
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
House (3 Bedrooms) | Interior

Riverfront Relaxation: Secluded Jacksonville Home

Riverfront Relaxation: Secluded Jacksonville Home
3.0 star property
Jacksonville
The price is NZ$745
includes taxes & fees
14 June - 15 June
Riverfront Relaxation: Secluded Jacksonville Home
Exterior

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, (32 reviews)
"Location was quiet and private, perfect for a break from busy schedule. Cottage was charming with especially comfortable couch and bed. Great surroundings for walking the dog. "
United States
T L.
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
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.

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
9.6 out of 10, Exceptional, (4 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.
The price is NZ$697
includes taxes & fees
25 June - 26 June
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

Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (69 reviews)
"Creatively decorated and cozy. Bed a bit lumpy but overall a lovely little cottage perfectly located next to Main Street."
United States
Nancy L.
The price is NZ$528
includes taxes & fees
15 June - 16 June
Historic Bradshaw House!
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, (2 reviews)
"Wonderful place and great location"
United States
darren t.
The Williams - luxe 2-bedroom cottage w/onsite parking in downtown Jacksonville
Exterior

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, (80 reviews)
"The host was very helpful and responsive to questions. The location was wonderful, and the property was clean and warm. A very nice place to stay!"
United States
Sarah F.
The price is NZ$648
includes taxes & fees
16 June - 17 June
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.
Exterior

Fireside Cottage in Downtown Jacksonville

Fireside Cottage in Downtown Jacksonville
Jacksonville Historic District
The price is NZ$457
includes taxes & fees
15 June - 16 June
Fireside Cottage in Downtown Jacksonville
Exterior

Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.0 out of 10, Wonderful, (7 reviews)
"Location and interior was superb"
United States
Jonathan B.
The price is NZ$511
includes taxes & fees
15 June - 16 June
Charming 1BR Cottage – Walk to Britt Gardens
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

Timbers INN and Suites

Timbers INN and Suites

10/10 Excellent
"Excellent place! Clean and cozy, comfortable bed, good location, friendly staff. Everything you need for a pleasant time in Ashland. Would absolutely stay again :)"
Julie 1-night trip
Posted 2 hours ago
Timbers INN and Suites

Find out more about Ashland

Ashland Cottages information

Number of reviews
735
Accommodation
127 Cottages
Lowest Price
NZ$307
Highest Price
NZ$745

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between NZ$307 and NZ$745 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.
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.
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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