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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Cottages in Ashland

Blue Gate Cottage on the Rogue River
Relax on the cabin's inviting porch, surrounded by lush greenery and serene natural surroundings.

Blue Gate Cottage on the Rogue River

9.8 out of 10, Exceptional, (28)
"We loved the area and the cabin"
Blue Gate Cottage on the Rogue River
The Ashland Cottage, walk to town
Relax on the deck with a grill and outdoor seating, and unwind in the cozy living area with a sofa and rug.

The Ashland Cottage, walk to town

10.0 out of 10, Exceptional, (201)
"Cute, friendly and convenient."
$263 nightly
The price is $293
Aug 17 - Aug 18
Total includes taxes and fees
The Ashland Cottage, walk to town
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Experience the charm of Trolley Stop Antiques, a historic building with a balcony and sidewalk.

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

9.6 out of 10, Exceptional, (26)
"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. "
$215 nightly
The price is $218
Aug 10 - Aug 11
Total includes taxes and fees
Cozy Cottage on Applegate River Micro-Farm at Vineyards.15 Min to Jacksonville
Courtside Cottage - WalkScore 93 - Dog Friendly
Enjoy cooking in this well-equipped kitchen with a dishwasher, microwave, and coffee maker.

Courtside Cottage - WalkScore 93 - Dog Friendly

10.0 out of 10, Exceptional, (48)
"Great location and very cute place. "
$302 nightly
The price is $337
Sep 1 - Sep 2
Total includes taxes and fees
Courtside Cottage - WalkScore 93 - Dog Friendly
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and central island.

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

10.0 out of 10, Exceptional, (13)
"This is a great spot to stay. "
$292 nightly
The price is $325
Sep 6 - Sep 7
Total includes taxes and fees
Casa Amore Ashland~Pet-Friendly~Walkable to the Plaza, OSF, Restaurants & More
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Prepare your morning coffee in this well-equipped kitchen.

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. "
$158 nightly
The price is $178
Aug 14 - Aug 15
Total includes taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Cozy retreat with a neatly made bed, wall-mounted light, and framed artwork.

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"
$220 nightly
The price is $247
Aug 12 - Aug 13
Total includes taxes and fees
HOLLY HOUSE ~ Organic, Dog-friendly Garden Cottage
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and ample storage.

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

10.0 out of 10, Exceptional, (38)
"Checkin was easy—they even were able to accommodate us when we got into town early. Very clean, awesome outdoor space, comfortable bed. We enjoyed the location, too! We would stay again!"
$319 nightly
The price is $353
Aug 14 - Aug 15
Total includes taxes and fees
Lily Pad - #1 BEST LOCATION, STUNNING, ROMANTIC, FULL KITCHEN, OUTDOOR FIRE PIT
Ida's Cottage Jacksonville
Guests can enjoy a porch with a column and mailbox, adjacent to a driveway and street.

Ida's Cottage Jacksonville

9.6 out of 10, Exceptional, (74)
"Excellent quiet location close to down town. Bedroom set up was perfect for us. "
Ida's Cottage Jacksonville
Paschal Winery
Enjoy cooking in this well-equipped kitchen with a large island, sink, and stove.

Paschal Winery

4.5 star property
9.6 out of 10, Exceptional, (10)
"Very nice and hassle free check in "
$259 nightly
The price is $263
Aug 14 - Aug 15
Total includes taxes and fees
Paschal Winery
TIGERS DEN - #1 BEST LOCATION, ROMANTIC, STUNNING, STEPS TO BRITT FESTIVAL
Relax in this serene space with a beige sofa, wooden floor, and large mirror.

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
Ashland's Mountain View Vacation Rental.
Set amidst a beautifully landscaped yard, this charming home features a stone foundation and a sloped roof.

Ashland's Mountain View Vacation Rental.

9.8 out of 10, Exceptional, (38)
"This is a wonderful property!! Very comfortable!!"
Ashland's Mountain View Vacation Rental.
Standish Cottage is Creekside
Stroll through the serene garden, surrounded by lush ferns and broad-leafed vegetation, along a winding gravel path.

Standish Cottage is Creekside

10.0 out of 10, Exceptional, (62)
"Really Loved our SF stay at Standish cottage in Jacksonville"
Standish Cottage is Creekside
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Relax on the covered patio with outdoor furniture, perfect for unwinding in the fresh air.

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

9.8 out of 10, Exceptional, (22)
"Had family in the area and was able to visit."
$257 nightly
The price is $261
Aug 25 - Aug 26
Total includes taxes and fees
Charming Cottage near historic Jacksonville. Wi-Fi, fenced pet area.
Jacksonville Towne Square.
Cozy living area with leather sofa, dining table for four, and kitchen in the background.

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!
Situated in a wooded area, this cozy home offers a patio with a tiled floor, sheltered seating area and a white picket fence.

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!
Luxury Cottage in Jacksonville's Historic Core!
Relax in a serene garden oasis with a central fountain and two benches.

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!
Remote Escape: Klamath Falls Cabin By Lake & Hikes
House (1 Bedroom) | Interior

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
Downtown Mint
Stunning garden surrounds this charming home with a distinctive yellow front door and a covered porch.

Downtown Mint

9.8 out of 10, Exceptional, (34)
"We came to visit family and this place was perfect. We really enjoyed it."
$210 nightly
The price is $236
Aug 11 - Aug 12
Total includes taxes and fees
Downtown Mint
Central Medford Family Retreat w/ Large Yard!
Stroll through the serene garden, surrounded by lush plants and a wooden pergola, with a shaded seating area under the structure.

Central Medford Family Retreat w/ Large Yard!

3.0 star property
Central Medford Family Retreat w/ Large Yard!
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

Flagship Inn of Ashland

Flagship Inn of Ashland

10/10 Excellent
"Great place to stay with family on a roadtrip! "
kristen 1-night trip
Posted 19 hours ago
Flagship Inn of Ashland