Search Cottages in Ashland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 98 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 469
AED 825 total
includes taxes & fees
24 Feb - 25 Feb
Paschal Winery

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 377
AED 830 total
includes taxes & fees
26 Feb - 27 Feb
Courtside Cottage - WalkScore 93 - Dog Friendly

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 712 total
includes taxes & fees
24 Feb - 25 Feb
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

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
24 Feb - 25 Feb
The Ashland Cottage, walk to town

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 1,052 total
includes taxes & fees
24 Feb - 25 Feb
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

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 645 total
includes taxes & fees
24 Feb - 25 Feb
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!

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 444
AED 748 total
includes taxes & fees
24 Feb - 25 Feb
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

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, (88)
"Lovely space with lots of little welcoming details. It was very clean and close to the places I needed to visit during my stay. I only used the space for one night, arriving early in the evening and leaving early in the morning. It was a comfortable alternative to a hotel. "
The price is AED 323
AED 603 total
includes taxes & fees
5 Mar - 6 Mar
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Downtown Mint

10.0 out of 10, Exceptional, (31)
"Spent Christmas here to be with a family member that lives in Medford. Kitchen was well stocked and were able to make all the meals for the holiday celebration and even able to make gingerbread cookies. Very close to stores and restaurants. Owner was very responsive to any questions and stopped by to greet us as we checked in."
The price is AED 294
AED 744 total
includes taxes & fees
24 Feb - 25 Feb
Downtown Mint

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

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

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
1 Mar - 2 Mar
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT

Blue Gate Cottage on the Rogue River

9.8 out of 10, Exceptional, (26)
"Stayed 5 days and still was not enough Privare part of the riverthe river the most beautiful"
Blue Gate Cottage on the Rogue River

Historic Bradshaw House!

10.0 out of 10, Exceptional, (64)
"We LOVED this cute little house. It was cozy and so close to downtown. It was wonderful. "
Historic Bradshaw House!

Sherman Lofthouse~Old East Medford~Walkable to Downtown

Sherman Lofthouse~Old East Medford~Walkable to Downtown

Luxury Cottage in Jacksonville's Historic Core!

10.0 out of 10, Exceptional, (49)
"Our stay at the cottage was fantastic! Jackie, has thought of every detail to provide comfort and style. She went the extra mile by leaving a wonderful snack basket and a warm friendly note. The cottage is in great walking distance to downtown and the local grocery store, which we loved. The bed and linens were very comfortable! We also appreciated the information binder that included details on how to operate the lights, remote controls and navigating Jacksonville. "
Luxury Cottage in Jacksonville's Historic Core!

The Cottage!

2.0 star property
6.8 out of 10, (3)
"Cute cottage for 1 or 2 people. It was 100 degrees outside but the AC worked great to keep it cool inside. The kitchen is fully equipped with everything to cook a nice meal. Nice clean decor and linens. Located just 1/2 block from shops and restaurants, walk everywhere easily including Britt Fest. Friendly town with a nice variety of things to explore including nearby hiking trails."
The Cottage!
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.
Don't see what you're looking for?
See all available properties in Ashland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (30)
The price is AED 551
AED 819 total
includes taxes & fees
24 Feb - 25 Feb
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 1,010
AED 2,224 total
includes taxes & fees
24 Feb - 25 Feb
Charming home, w/hot tub, close to downtown Pet-Friendly!

Ashland Lodge w/ Lake Views & Game Room Loft

10.0 out of 10, Exceptional, (68)
"Our family and friends had the best time. Would recommend to anyone that is looking for some peace and quiet. "
Ashland Lodge w/ Lake Views & Game Room Loft
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?
Rates for cottages in Ashland range between AED 294 and AED 657 per night. No matter your budget, you’ll find an ideal place to get in touch with nature. 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 9.5. Oak Street Cottages is a superb option if you’re into nature and an easygoing pace. Travelers staying at this 3-star stay will have access to a barbecue grill and a fireplace. The Retreat At Oak Knoll ~ Pet Friendly is another popular choice. This 4-star cottage has a garden and a yard.
How many cottages are there in Ashland?
Pick from 98 cottages in Ashland. Whether you’re vacationing with the family or planning a weekend escape with close friends, Expedia will help you find the ideal space to immerse yourself in nature.
Are there any 5-star cottages in Ashland?
Ashland doesn’t have any 5-star cottages — but you and your buddies can still have a stylish stay here! Why not try C’ Street Station - Short Walk To Osf? Located around 0.80 kilometers from downtown, this 4-star retreat comes with a fireplace and free WiFi. The Retreat At Oak Knoll ~ Pet Friendly is another wonderful 4-star pick just 5 kilometers from central Ashland. It offers a laid-back vibe close to nature on top of amenities like a living room and a garden.
Why book your cottage in Ashland with Expedia?
Expedia has some great cottages in Ashland, so get set for an unforgettable vacay on nature’s doorstep. If you have a fixed budget, click on how much you’d like to spend and your preferred property star rating. Or, try out our filters to search for cottages with a pool or a kitchen. We’ll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Ashland?
With Expedia’s handy filter tool, locating cheap cottages in Ashland is easy. To find stays that’ll make your wallet smile, refine your search by amenities, budget and star rating.