Ashland Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Ashland Vacation Homes

Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views
Escape to a secluded cabin surrounded by nature, with a deck offering a barbecue grill and outdoor seating.

Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views

9.4 out of 10, Exceptional, (44)
"Very large home with everything we needed and more. Great setting and very close to Crater Lake."
Harriman Springs Resort Cabin 1 - A Vacation House with Accommodations & Views
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 CA $205
CA $390 total
includes taxes & fees
Aug 18 - Aug 19
East Main Downtown Bungalow
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, (8)
"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 CA $276
CA $560 total
includes taxes & fees
Aug 13 - Aug 14
A beautiful Skyfall Landing
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
Entertainment Home on Golf Course - Hot Tub /Pool
Relax in a peaceful outdoor space with a grill, water feature, and comfortable seating under shaded umbrellas.

Entertainment Home on Golf Course - Hot Tub /Pool

10.0 out of 10, Exceptional, (6)
"It was amazing! Great home for a family! "
Entertainment Home on Golf Course - Hot Tub /Pool
Comfy Cozy Casa
Enter a cozy living space with a plush sofa, side table, and warm lighting.

Comfy Cozy Casa

10.0 out of 10, Exceptional, (52)
"We had a great experience at this property and it was close in proximity to an event that we attended."
The price is CA $255
CA $511 total
includes taxes & fees
Sep 8 - Sep 9
Comfy Cozy Casa
New Downtown 3 Bedroom Upstairs Flat with views
Fully equipped kitchen with stainless steel appliances, white cabinets, and ample counter space.

New Downtown 3 Bedroom Upstairs Flat with views

9.6 out of 10, Exceptional, (29)
"We have now stayed Amber‘s place five or six times and each time it has been delightful. It is in a convenient location, the deck has a fabulous view, we always have a quick response for anything we need. We are already looking forward to our next visit."
New Downtown 3 Bedroom Upstairs Flat with views
Winchester family home
Enjoy al fresco dining on this patio, complete with a barbecue grill and lush greenery.

Winchester family home

9.2 out of 10, Wonderful, (25)
"The place was clean and a lovley place to stay "
Winchester family home
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
Enjoy a serene home with a covered porch, beautifully manicured lawn, and a garden featuring a variety of flowering plants.

1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer

2.0 star property
10.0 out of 10, Exceptional, (13)
"Clean quiet comfortable"
The price is CA $165
CA $358 total
includes taxes & fees
Aug 25 - Aug 26
1 king bed 1 queen bed 2 bedroom house with AC, WiFi and washer and dryer
This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.
Enjoy cooking in this well-equipped kitchen with a central island, oven, and microwave.

This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.

The price is CA $224
CA $387 total
includes taxes & fees
Sep 8 - Sep 9
This house is a 3 bedroom(s), 2 bathrooms, located in Central Point, OR.
The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7
Enjoy cooking in this well-equipped kitchen with a microwave, oven, and refrigerator.

The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7

The price is CA $199
CA $439 total
includes taxes & fees
Aug 18 - Aug 19
The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7
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 CA $279
CA $706 total
includes taxes & fees
Aug 18 - Aug 19
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
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!
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 CA $215
CA $337 total
includes taxes & fees
Aug 11 - Aug 12
Jacksonville Place
"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 CA $316
CA $559 total
includes taxes & fees
Aug 11 - Aug 12
Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!
BF Dowell House
Experience a traditional two-story home with a charming porch and beautifully maintained garden, surrounded by trees and a serene landscape.

BF Dowell House

9.8 out of 10, Exceptional, (63)
"We invited 3 long time couple friends to come visit us in Jacksonville. They stayed in the BF Dowell House and loved it. They wanted to make sure I left a good review because they were so impressed with how clean and well organized it was. They yard was so lovely too. We definitely recommend it!!"
BF Dowell House
The Madrone House, Country Getaway with Mountain Views and Fresh Air.
Surrounded by natural beauty, this serene retreat offers a tranquil escape with a balcony overlooking the landscape.

The Madrone House, Country Getaway with Mountain Views and Fresh Air.

10.0 out of 10, Exceptional, (67)
"We had a wonderful stay at the Madrone House. It was clean, comfortable and fully stocked which made cooking easy! The views are incredible and we saw deer multiple times. Would definitely stay again!"
The Madrone House, Country Getaway with Mountain Views and Fresh Air.
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, (57)
"Great location - close to restaurants and shops! "
Premier Downstairs Flat in Perfect Down Town Location
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 CA $198
CA $526 total
includes taxes & fees
Aug 25 - Aug 26
Downtown Ashland House - Walk to Plaza and OSF!
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

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

10/10 Excellent
"Beautiful location, mid century modern resort, with all the services. Electric charging, lush landscaping and spotless clean well equipped rooms. Highly recommend, especially as it’s pet friendly with a fenced in dog park at the rear."
John 1-night trip
Posted 19 hours ago
Ashland Hills Hotel & Suites