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Featured Cottages in Ashland and around

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

10.0 out of 10, Exceptional, (14)
"This is a great spot to stay. "
The price is €356
includes taxes & fees
14 Sept - 15 Sept
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More

The Ashland Cottage, walk to town

10.0 out of 10, Exceptional, (201)
"Cute, friendly and convenient."
The Ashland Cottage, walk to town

Downtown Mint

9.8 out of 10, Exceptional, (37)
"We came to visit family and this place was perfect. We really enjoyed it."
The price is €206
includes taxes & fees
17 Aug - 18 Aug
Downtown Mint

HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

9.2 out of 10, Wonderful, (13)
"Great location Clean cute cottage with everything we needed for our stay. Would definitely stay again"
The price is €226
includes taxes & fees
14 Sept - 15 Sept
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage

Standish Cottage is Creekside

10.0 out of 10, Exceptional, (63)
"Really Loved our SF stay at Standish cottage in Jacksonville"
Standish Cottage is Creekside

Cottage Eleven in the Heart of Jacksonville!!

Cottage Eleven in the Heart of Jacksonville!!

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (10)
"Very nice and hassle free check in "
The price is €233
includes taxes & fees
25 Aug - 26 Aug
Paschal Winery

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

9.8 out of 10, Exceptional, (96)
"This was a very nice studio, the owners were very nice and easy to work with. "
The price is €156
includes taxes & fees
18 Aug - 19 Aug
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Remote Escape: Klamath Falls Cabin By Lake & Hikes

2.0 star property
10.0 out of 10, Exceptional, (1)
"The cabin was amazing! Very cool log cabin vibe with all of the decorations to make you feel like you're roughing it in the woods but with all the modern convenience to make it comfortable. The outdoor bathtub and grilling area were standouts. The cabin actually does have AC even though the listing says it doesn't so that was a relief for a summer getaway. We came to see Crater Lake and it was close enough to recommend it for anyone wanting to see crater along with lake activities closer by at...
Remote Escape: Klamath Falls Cabin By Lake & Hikes

Tranquil setting surrounded by panoramic mountain views, grazing horses

9.8 out of 10, Exceptional, (112)
"We found this Farmhouse Cottage to be a wonderful retreat after a day of touring what the local area has to offer. It is quiet, the hosts are enjoyable to meet and get to know, and the variety of birds on the property were fun to watch and listen to."
Tranquil setting surrounded by panoramic mountain views, grazing horses

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

10.0 out of 10, Exceptional, (36)
"Easy check in and very helpful host!"
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL

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

9.6 out of 10, Exceptional, (27)
"Wonderful stay at this cute cottage with my adult daughters. Owners were great and we enjoyed every minute of it. Can't wait to come back again. "
The price is €193
includes taxes & fees
24 Aug - 25 Aug
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville

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

9.0 out of 10, Wonderful, (14)
"The house is very cozy great set up! I wish i would have know it was in a trailer park! "
This cottage is a 1 bedroom(s), 1 bathrooms, located in Gold Hill, OR.

Courtside Cottage - WalkScore 93 - Dog Friendly

10.0 out of 10, Exceptional, (51)
"Lovely studio cottage with high-end kitchenette, king bed, gorgeous bathroom, and thoughtful touches everywhere. Plus, had a slight problem with the microwave and the owner called from Japan to help us solve it (CFI tripped). I have been to Ashland before and this is really well situated but off a main street so private and quiet."
The price is €274
includes taxes & fees
1 Sept - 2 Sept
Courtside Cottage - WalkScore 93 - Dog Friendly

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

9.8 out of 10, Exceptional, (23)
"Had family in the area and was able to visit."
The price is €220
includes taxes & fees
8 Sept - 9 Sept
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.

Jacksonville Towne Square.

3.0 star property
9.4 out of 10, Exceptional, (12)
"great location. you can easily walk to shops and restaurants. "
Jacksonville Towne Square.

The Cottage!

2.0 star property
7.6 out of 10, Good, (4)
"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!

Historic Bradshaw House!

10.0 out of 10, Exceptional, (65)
"Would definitely stay here again, the location is perfect for walking around downtown. It was such a lovely, cozy home to stay in too. Would recommend!"
Historic Bradshaw House!

Luxury Cottage in Jacksonville's Historic Core!

10.0 out of 10, Exceptional, (50)
"Loved this place! Right in the heart of J-ville. Our host was fantastic and super responsive. The attention to details and comfort in the house was top-quality. "
Luxury Cottage in Jacksonville's Historic Core!

🌻 Charming Cottage On Peaceful 5 Acres in the Mountains

9.0 out of 10, Wonderful, (8)
"This place was amazing. Took a little extra time to get to, but it was well worth it. Would definitely stay here again. Thanks again for all necessary accommodations as well. Definitely appreciated 🙏"
The price is €182
includes taxes & fees
15 Aug - 16 Aug
🌻 Charming Cottage On Peaceful 5 Acres in the Mountains
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

Frequently asked questions

How much do cottages in Ashland cost?
Cottages in Ashland range between €156 and €356 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 9.5. 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 120 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.