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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
In the historic railroad district, walking distance to all the best of Ashland!
Relax in the charming outdoor seating area of Paris Green, surrounded by lush potted plants and a picturesque tree.

In the historic railroad district, walking distance to all the best of Ashland!

10.0 out of 10, Exceptional, (186)
"Lovely old-fashioned cottage for friends to share"
In the historic railroad district, walking distance to all the best of Ashland!
A beautiful Skyfall Landing
Relax by the pool surrounded by a deck and seating area with outdoor furniture.

A beautiful Skyfall Landing

10.0 out of 10, Exceptional, (7)
"The home is clean, comfortable, and spacious. The bedrooms are a great size, beds are comfortable and rooms are private. Very easy access private drive up. Peaceful backyard view and a few steps to the salt water pool and hot tub. Fishing, hunting, or just relaxing we will stay again..."
The price is HK$1,378
HK$2,968 total
includes taxes & fees
13 Aug - 14 Aug
A beautiful Skyfall Landing
Riverfront on the Rogue! Ideal Southern Oregon location
Relax in a cozy cabin with a fire pit and outdoor seating area surrounded by lush greenery and a serene body of water.

Riverfront on the Rogue! Ideal Southern Oregon location

9.8 out of 10, Exceptional, (54)
"Enjoyed our time in the area. "
Riverfront on the Rogue! Ideal Southern Oregon location
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Relax in the backyard hot tub, surrounded by a deck and a grassy area.

Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

10.0 out of 10, Exceptional, (47)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is HK$2,159
HK$4,753 total
includes taxes & fees
22 Aug - 23 Aug
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Jacksonville Place
Enjoy cooking in the spacious kitchen with a central island, stovetop, and oven, adjacent to a dining area with a wooden table and chairs.

Jacksonville Place

9.0 out of 10, Wonderful, (22)
"We enjoyed our stay here. When we first arrived, the cleaning staff was on their way. We left for dinner and came back to a clean house. We had what we needed for the 3 nights we were in town and plenty of room for me, my husband, three daughters and my mom. Fair price and decent place to stay. I’m sure we would stay here again if we come back through this area. "
The price is HK$1,222
HK$1,914 total
includes taxes & fees
12 Aug - 13 Aug
Jacksonville Place
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Relax on the porch with comfortable wicker chairs and a small table, surrounded by lush greenery and a charming entrance.

BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown

9.6 out of 10, Exceptional, (79)
"The cottage was clean, comfortable, and very well situated in town. The kitchen was well equipped, allowing us to cook most of our meals there. It's in a quiet neighborhood where you can walk to anything you might want."
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Premier Downstairs Flat in Perfect Down Town Location
Kitchen features a dishwasher, sink, coffee maker, and a window with blinds.

Premier Downstairs Flat in Perfect Down Town Location

10.0 out of 10, Exceptional, (56)
"Great location - close to restaurants and shops! "
Premier Downstairs Flat in Perfect Down Town Location
House + 2 Studios- 3 blocks from the Plaza!
Relax in this inviting living room with a round coffee table, two sofas, and a dining area.

House + 2 Studios- 3 blocks from the Plaza!

9.8 out of 10, Exceptional, (8)
"The house and studios were perfect for my 4 friends and myself. The location was amazing and we could walk to most of our destinations. I highly recommend staying at this house."
The price is HK$2,104
HK$5,169 total
includes taxes & fees
17 Aug - 18 Aug
House + 2 Studios- 3 blocks from the Plaza!
East Main Downtown Bungalow
Enjoy cooking in this kitchen with a central island, dishwasher, and refrigerator.

East Main Downtown Bungalow

9.2 out of 10, Wonderful, (32)
"Pros: Excellent location. Good communication with hosts. Cons: Only big enough for two adults to stay, possibly a child on the couch. The description said it accommodates 4 people, but the couch isn’t big enough for adults. Also, the water in the bathroom doesn’t allow use of shower and sink at the same time."
The price is HK$1,193
HK$2,214 total
includes taxes & fees
1 Sept - 2 Sept
East Main Downtown Bungalow
Spacious Grants Pass Home w/ Hot Tub & River Views
Enjoy cooking in this well-lit kitchen with a large island, stove, and dining area with a backyard view.

Spacious Grants Pass Home w/ Hot Tub & River Views

9.4 out of 10, Exceptional, (26)
"We loved the property. The house was impeccably clean. "
Spacious Grants Pass Home w/ Hot Tub & River Views
Nightly or short term rental in Medford.
Stylish home with a garage and beautifully maintained garden.

Nightly or short term rental in Medford.

2.0 star property
9.0 out of 10, Wonderful, (2)
"We booked this home for my client who was displaced from his home due to water damage. The host was extremely communicative and accommodating. Highly recommend. "
Nightly or short term rental in Medford.
Spectacular large custom home with a pool!
Relax by the fire pit in a cozy outdoor seating area surrounded by Adirondack chairs.

Spectacular large custom home with a pool!

9.6 out of 10, Exceptional, (13)
"Beautiful home and beautiful stay"
Spectacular large custom home with a pool!
The River House with Views of the Famous Rogue River! No cleaning fees!
Set amidst a forest, this lodge offers a tranquil retreat with a spacious balcony and a stone facade.

The River House with Views of the Famous Rogue River! No cleaning fees!

9.8 out of 10, Exceptional, (34)
"House was amazing and we enjoyed are stay."
The price is HK$1,578
HK$1,824 total
includes taxes & fees
7 Sept - 8 Sept
The River House with Views of the Famous Rogue River! No cleaning fees!
"Enchantment" Medford, Oregon
Enjoy meals with family and friends at the large dining table, surrounded by expansive forest views.

"Enchantment" Medford, Oregon

9.8 out of 10, Exceptional, (37)
"Carol was amazing and we enjoyed our stay here! Very responsive and clean. Highly recommend staying here!"
"Enchantment" Medford, Oregon
Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!
Property grounds

Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!

10.0 out of 10, Exceptional, (5)
"Great memories made here! The space was nicely decorated, it was clean, modern, and well equipped."
The price is HK$1,805
HK$3,188 total
includes taxes & fees
11 Aug - 12 Aug
Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!
Station House Suite A
Modern kitchen with central island, sink, and stove, adjacent to a living area with a brick wall and staircase.

Station House Suite A

9.8 out of 10, Exceptional, (18)
"Every detail thought of for an enjoyable stay. "
The price is HK$1,354
HK$3,304 total
includes taxes & fees
11 Aug - 12 Aug
Station House Suite A
Beautiful Luxury Cottage. Walk To It All!
Enjoy outdoor dining or relaxation on the covered patio with a bench and table.

Beautiful Luxury Cottage. Walk To It All!

10.0 out of 10, Exceptional, (120)
"Clean, lots of amenities, centrally located and very comfy bed. Enjoyed our stay. Thank you!"
Beautiful Luxury Cottage. Walk To It All!
Downtown Ashland House - Walk to Plaza and OSF!
Relax in this inviting living room with two sofas, a coffee table, and a cozy rug.

Downtown Ashland House - Walk to Plaza and OSF!

9.8 out of 10, Exceptional, (41)
"Perfect location; cute house - enjoyed our stay very much !"
The price is HK$1,130
HK$3,002 total
includes taxes & fees
25 Aug - 26 Aug
Downtown Ashland House - Walk to Plaza and OSF!
California Cottage: Downtown!
Kitchen features a sink, coffee maker, and wooden countertop.

California Cottage: Downtown!

9.8 out of 10, Exceptional, (32)
"Wonderful property, clean, spacious and great location with walking distance to restaurants. Excellent communication with property manager."
The price is HK$894
HK$1,802 total
includes taxes & fees
11 Aug - 12 Aug
California Cottage: Downtown!
Cheerful 3-Bedroom home in Central Point
Enjoy cooking in this kitchen with a central island, microwave, and window offering a view of the outdoors.

Cheerful 3-Bedroom home in Central Point

10.0 out of 10, Exceptional, (17)
"Quick trip with the fellas, and enjoyed the hospitality."
Cheerful 3-Bedroom home in Central Point
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 Historic Jacksonville Hotel Reviews

Stratford Inn

Stratford Inn

10/10 Excellent
"The Stratford Inn was the perfect base for our weekend in Ashland attending the Oregon Shakespeare Festival! Location was within 5 minutes of all the shops and restaurants, maybe 8 minutes from the theaters. The staff was incredibly friendly and helpful, both at the front desk and at the breakfast service. We especially appreciated the pool being open late and breakfast going until 10am. We will definitely stay here again!"
Teresa 2-night trip
Posted 1 day ago
Stratford Inn