Holiday Homes in Ashland

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Ashland and around

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

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
Microwave, dishwasher

East Main Downtown Bungalow

9.2 out of 10, Wonderful, (33)
"Great location and the space was extremely functional and well thought out!"
The price is €246
includes taxes & fees
18 Aug - 19 Aug
East Main Downtown Bungalow
A beautiful Skyfall Landing
Outdoor pool

A beautiful Skyfall Landing

10.0 out of 10, Exceptional, (9)
"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 €374
includes taxes & fees
14 Aug - 15 Aug
A beautiful Skyfall Landing
BLOSSOM VIEW COTTAGES - Charming Home near OSF Plaza and Downtown
Terrace/patio

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
Outdoor dining

Entertainment Home on Golf Course - Hot Tub /Pool

10.0 out of 10, Exceptional, (7)
"We had an amazing time. The property is beautiful and the hosts are very responsive and easy to work with. The house is so amazing, you won’t want to leave."
Entertainment Home on Golf Course - Hot Tub /Pool
Comfy Cozy Casa
Interior

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 €356
includes taxes & fees
8 Sept - 9 Sept
Comfy Cozy Casa
New Downtown 3 Bedroom Upstairs Flat with views
Fridge, microwave, oven, stovetop

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
Terrace/patio

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
Exterior

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, (14)
"Clean quiet comfortable"
The price is €230
includes taxes & fees
17 Aug - 18 Aug
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.
Fridge, microwave, oven, stovetop

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

The price is €248
includes taxes & fees
8 Sept - 9 Sept
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
Fridge, microwave, oven, stovetop

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

The price is €281
includes taxes & fees
18 Aug - 19 Aug
The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Outdoor spa tub

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

10.0 out of 10, Exceptional, (48)
"Very charming home with everything you need to relax and enjoy a vacation in Ashland, Oregon."
The price is €451
includes taxes & fees
18 Aug - 19 Aug
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!
Outdoor dining

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
Fridge, microwave, oven, stovetop

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 €211
includes taxes & fees
26 Aug - 27 Aug
Jacksonville Place
"Enchantment" Medford, Oregon
Outdoor dining

"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 €357
includes taxes & fees
14 Aug - 15 Aug
Station House Suite B~Downtown Jacksonville~Rooftop Patio~Walking Distance to Britt!
BF Dowell House
Exterior

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.
Property grounds

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
Fridge, microwave, oven, stovetop

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!
Smart TV, books

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 €331
includes taxes & fees
25 Aug - 26 Aug
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
"Beds were very comfortable and room was spacious and very clean. Front desk staff was friendly and efficient. Hotel gym had a variety of machines. "
Alice 1-night trip
Posted 20 hours ago
Ashland Hills Hotel & Suites