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Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 June - 28 June

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 AU$313
includes taxes & fees
10 Mar - 11 Mar
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, (214 reviews)
"Perfect Stay!"
United States
Anonymous traveller
The price is AU$405
includes taxes & fees
4 Mar - 5 Mar
The Ashland Cottage, walk to town
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 reviews)
"Great location, many personal touches and the host cares about comfort! Will stay again, thanks so much! "
United States
Krista M.
The price is AU$523
includes taxes & fees
4 Mar - 5 Mar
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, (62 reviews)
"Great place to stay very quaint very clean. Host is very gracious and communicated perfectly before the trip. Definitely would stay here again."
United States
Lantz B.
The price is AU$306
includes taxes & fees
4 Mar - 5 Mar
Courtside Cottage - WalkScore 93 - Dog Friendly
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, (9 reviews)
"Enjoyed our stay"
United States
Julie M.
The price is AU$315
includes taxes & fees
20 Mar - 21 Mar
Charming carriage house in Ashland near downtown
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 reviews)
"Close to everything; dog had plenty of room. Our go-to in Ashland; looking forward to staying again!"
United States
David A.
The price is AU$556
includes taxes & fees
14 Mar - 15 Mar
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Smart TV, books

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

Railroad District, steps to downtown, everything you need to enjoy Ashland!
Historic Railroad District
The price is AU$789
includes taxes & fees
4 Mar - 5 Mar
Railroad District, steps to downtown, everything you need to enjoy Ashland!
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 reviews)
"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
The price is AU$267
includes taxes & fees
11 Mar - 12 Mar
On-site Winery & Tasting Room: Oregon Bungalow!
Terrace/patio

Paschal Winery

Paschal Winery
4.5 star property
Talent
9.6 out of 10, Exceptional, (15 reviews)
"Great space and beautiful views. 10/10 experience. "
United States
Cody
The price is AU$287
includes taxes & fees
18 Mar - 19 Mar
Paschal Winery
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, (105 reviews)
"The stay was private and great "
United States
bradley s.
The price is AU$221
includes taxes & fees
4 Mar - 5 Mar
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Exterior

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
City Center Medford
9.4 out of 10, Exceptional, (23 reviews)
"Great property everything we needed close to town perfect stay!"
United States
Chuck F.
The price is AU$335
includes taxes & fees
4 Mar - 5 Mar
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
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, (4 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.
The price is AU$279
includes taxes & fees
9 Mar - 10 Mar
Peaceful Countryside Stay with Scenic Views- 5 minutes to Jacksonville
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 AU$317
includes taxes & fees
4 Mar - 5 Mar
Rosewood Studio | Private Cottage Near Downtown
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 reviews)
"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.
The price is AU$309
includes taxes & fees
12 Mar - 13 Mar
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Exterior detail

This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.

This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
Jacksonville Historic District
9.8 out of 10, Exceptional, (78 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 AU$428
includes taxes & fees
15 Mar - 16 Mar
This cottage is a 2 bedroom(s), 2 bathrooms, located in Jacksonville, OR.
Exterior

Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (68 reviews)
"Great highly recommend"
United States
Linda J.
The price is AU$439
includes taxes & fees
4 Mar - 5 Mar
Historic Bradshaw House!
Exterior

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, (27 reviews)
"Great host, cute surroundings, lovely stay."
United States
Katie B.
The price is AU$324
includes taxes & fees
31 Mar - 1 Apr
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
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, (48 reviews)
"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.
The price is AU$422
includes taxes & fees
9 Mar - 10 Mar
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, & 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, (2 reviews)
"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.
The price is AU$331
includes taxes & fees
4 Mar - 5 Mar
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

Charming 1BR Cottage – Walk to Britt Gardens

Charming 1BR Cottage – Walk to Britt Gardens
Jacksonville
9.0 out of 10, Wonderful, (7 reviews)
"Perfect downtown location and much nicer than the pictures show. "
United States
Lesha B.
The price is AU$432
includes taxes & fees
4 Mar - 5 Mar
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

McCall House Boutique Inn

McCall House Boutique Inn

10/10 Excellent
"Room clean, great breakfast"
Phyllis 1-night trip
Posted 2 days ago
McCall House Boutique Inn

Find out more about Ashland

Ashland Cottages information

Number of reviews
686
Accommodation
129 Cottages
Lowest Price
AU$221
Highest Price
AU$789

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AU$221 and AU$789 per night. These retreats offer a chance to soak up nature's beauty — at a price you can afford. This price was 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?
You'll find 129 cottages in Ashland. No matter if you're travelling with the kids or planning a weekend retreat with your buddies, Expedia can help you find the perfect place to reacquaint yourself with nature.
What is there to do in Ashland near my cottage?
You'll find loads of terrific things that'll fill up your itinerary in Ashland. Explore leading attractions like Oregon Shakespeare Festival, Mount Ashland Ski Area and Oregon Cabaret Theatre. Allen Elizabethan Theatre, Thomas Theatre and Angus Bowmer Theatre are other must-see's.

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