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Compare 99 Cottages in Ashland with updated reviews, rates, and availability.

Paschal Winery

4.5 star property
9.4 out of 10, Exceptional, (6)
"Very nice and hassle free check in "
The price is AED 413
AED 768 total
includes taxes & fees
14 Apr - 15 Apr
Paschal Winery

Downtown Mint

10.0 out of 10, Exceptional, (32)
"The cottage was located downtown near everything and the beds & linens were an excellent quality. There were coffee beans and a grinder, olive oil salt & pepper. Those things while small make the stay easy and comfortable. "
The price is AED 294
AED 752 total
includes taxes & fees
17 Mar - 18 Mar
Downtown Mint

The Ashland Cottage, walk to town

10.0 out of 10, Exceptional, (191)
"We'll be back!"
The price is AED 624
AED 1,073 total
includes taxes & fees
17 Mar - 18 Mar
The Ashland Cottage, walk to town

Courtside Cottage - WalkScore 93 - Dog Friendly

10.0 out of 10, Exceptional, (39)
"Tastefully decorated, very comfortable and quiet! I truly enjoyed staying at the Courtside Cottage. Great location within walking distance to many options for great food and beverages. "
The price is AED 516
AED 1,005 total
includes taxes & fees
18 Mar - 19 Mar
Courtside Cottage - WalkScore 93 - Dog Friendly

TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL

10.0 out of 10, Exceptional, (34)
"Great location, just minutes walking to downtown Jacksonville and the britt festival."
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

9.0 out of 10, Wonderful, (2)
"This is a very charming and warm property located in a great central spot of Medford. I highly recommend it!"
The price is AED 474
AED 793 total
includes taxes & fees
17 Mar - 18 Mar
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

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

9.8 out of 10, Exceptional, (10)
"Casa Amore was a perfect spot for my daughter and her husband and their dog to stay for a night! The location is great, parking and entry is easy, the space is clean and comfortable with everything they needed, and the communication from Haley has been wonderful. "
The price is AED 551
AED 1,048 total
includes taxes & fees
17 Mar - 18 Mar
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

Charming carriage house in Ashland near downtown

The price is AED 422
AED 811 total
includes taxes & fees
22 Mar - 23 Mar
Charming carriage house in Ashland near downtown

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

9.6 out of 10, Exceptional, (18)
"Had family in the area and was able to visit."
The price is AED 364
AED 734 total
includes taxes & fees
26 Mar - 27 Mar
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

This cottage is a 1 bedroom(s), 1 bathrooms, located in Gold Hill, OR.

9.0 out of 10, Wonderful, (10)
"Really nice time at this stay! Chill and quiet environment! Clean and cozy! Will be back in the future! 5 stars! Thanks! "
The price is AED 413
AED 641 total
includes taxes & fees
17 Mar - 18 Mar
This cottage is a 1 bedroom(s), 1 bathrooms, located in Gold Hill, OR.

Cozy Central Point Bungalow on Working Winery!

10.0 out of 10, Exceptional, (5)
"Beautiful and relaxing property located close to just about everything! House was exactly as described!"
Cozy Central Point Bungalow on Working Winery!

Ashland Cabin on 170 Acres w/ Mtn Views & Sauna!

3.0 star property
Ashland Cabin on 170 Acres w/ Mtn Views & Sauna!

Jacksonville Towne Square.

3.0 star property
9.4 out of 10, Exceptional, (12)
"This townhouse is very nice. The primary bedroom suite is huge and well appointed. The 2nd bedroom (both are upstairs) has a queen bed and the bathroom is adjacent. The kitchen is excellent with very good appliances, up to date counter tops, etc. This was a perfect place for 2 couples to stay, and WAY better than getting 2 hotel rooms somewhere. (As an aside, a bit of touch up paint could easily cover up a few nicks/small holes in the walls in various rooms.)"
Jacksonville Towne Square.

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

9.8 out of 10, Exceptional, (90)
"It was freezing cold the 1st night and having it prepared for us with heat in the space would have been great. We had to buy TP and paper towels. We stayed 3 nights. The cabin is so cute the bed was excellent to sleep on. "
The price is AED 323
AED 603 total
includes taxes & fees
24 Mar - 25 Mar
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Tranquil setting surrounded by panoramic mountain views, grazing horses

9.8 out of 10, Exceptional, (107)
"This farmhouse cottage provides a very relaxing environment. We found its location to be central to a number of cities and attractions in the southern Oregon area. At the end of the day, we enjoyed looking forward to returning to this peaceful cottage."
Tranquil setting surrounded by panoramic mountain views, grazing horses

Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

9.6 out of 10, Exceptional, (19)
"We enjoyed our comfy stay in the country. We loved visiting with the animals. Unfortunately, the wineries weren’t open because it was Christmas but Jacksonville was decked out with lights. Thank you for adding to our fun winter adventure."
The price is AED 364
AED 719 total
includes taxes & fees
17 Mar - 18 Mar
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

Ashland's Mountain View Vacation Rental.

10.0 out of 10, Exceptional, (34)
"I was in town for a wedding. Stayed with a few friends and the place was perfect. Check in was very easy. The place was super clean. The beds were massive and soft. Make brunch each morning in the kitchen. Great stay! "
Ashland's Mountain View Vacation Rental.

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

10.0 out of 10, Exceptional, (36)
"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! "
The price is AED 657
AED 1,295 total
includes taxes & fees
24 Mar - 25 Mar
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Hiking Trail On-site: Mtn-view Eagle Point Retreat

3.0 star property
10.0 out of 10, Exceptional, (2)
"Very cute and cozy place to stay in the country. We met a bunch of wild turkey and deer in trip back and forth to home. The place was clean, inviting and privare. Enjoyed our stay!"
Hiking Trail On-site: Mtn-view Eagle Point Retreat

Standish Cottage is Creekside

10.0 out of 10, Exceptional, (60)
"We loved the location, size of house,and hope to relax there again when we need a place to stay while visiting our son and his family. "
Standish Cottage is Creekside
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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Other property types in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (30)
"Great room. We really loved staying here."
The price is AED 551
AED 819 total
includes taxes & fees
17 Mar - 18 Mar
A Cowslip's Belle Inn

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (34)
"super cool"
The price is AED 826
AED 1,990 total
includes taxes & fees
17 Mar - 18 Mar
Charming home, w/hot tub, close to downtown Pet-Friendly!

Quiet and peaceful cottage close to downtown

9.8 out of 10, Exceptional, (49)
"My daughter, my dog and I had a wonderful stay in this guest house! Perfect location? Ideal for dogs (doggy door and fenced yard), and we had everything we needed. We would definitely stay again!"
The price is AED 679
AED 1,216 total
includes taxes & fees
17 Mar - 18 Mar
Quiet and peaceful cottage close to downtown
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.

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between AED 294 and AED 657 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?
A traveler favorite is Oak Street Cottages. Make yourself comfortable at this 3-star stay which comes with a fireplace and a barbecue grill. The Retreat At Oak Knoll ~ Pet Friendly is another popular option worth checking out. Spend your break at this 4-star cottage and you’ll have access to amenities including a yard and a barbecue grill. You’ll have your pick of multiple cottages in Ashland with a total average guest review rating of 9.7.
How many cottages are there in Ashland?
Pack your suitcase and pick from 99 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 5-star cottages in Ashland?
There are no 5-star cottages in Ashland. However, there are some fabulous 4-star accommodations that are bound to impress you. Book a night or two at C’ Street Station - Short Walk To Osf, approximately 0.80 kilometers from the downtown area. free WiFi and a fireplace are a couple of the many conveniences available here. The Retreat At Oak Knoll ~ Pet Friendly is another upscale pick with a living room and a patio. This cozy cottage is around 5 kilometers from central Ashland.
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.