Ashland, OR Vacation Rentals

Our Favorite Vacation Rentals in Ashland

  • 'C' Street Station - Short walk to OSF
     Home/Apartment
    Booking.com
    From
    $172
  • Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown
     Home/Apartment
    Booking.com
    From
    $225
  • Art & Garden Cottage ~ Near Downtown
     Home/Apartment
    Booking.com
    From
    $156
  • Hopyard View Farm ~ A Farm Experience in Ashland!
     Home/Apartment
    Booking.com
    From
    $167
  • Dream Cottage at Paschal Winery
     Home/Apartment
    Booking.com
    From
    $202
  • Anderson Creek Barn Cottage - Minutes from Ashland
     Home/Apartment
    Booking.com
    From
    $183
  • Pioneer North & South - Closest to OSF!
     Country House
    Booking.com
    From
    $317
  • Hargadine House, the Carriage House
     Home/Apartment
    Booking.com
    From
    $275

Check prices for these upcoming dates

Ashland Vacation Rentals with a Pool

  • Garden Suite
    Excellent2br Home/Apartment
    Airbnb
    From
    $140
  • Pool table, Pool, Huge house! 5 queen bdrms!
    Excellent5br Home/Apartment
    Airbnb
    From
    $324
  • Angel Crest Guest Suite - East Medford Hills
    ExcellentHome/Apartment
    Airbnb
    From
    $85
  • Ashland Carter House, Carriage House!
    ExcellentHome/Apartment
    Airbnb
    From
    $180

Ashland Vacation Rentals with Wi-Fi

  • Charming Guest House - One block from Downtown!
    ExcellentHome/Apartment
    Airbnb
    From
    $161
  • Auburn Street Cottage in Ashland
    ExcellentHome/Apartment
    Airbnb
    From
    $184
  • Porscha's Hideaway Italian Upscale
    ExcellentHome/Apartment
    Airbnb
    From
    $234
  • Cozy camping close to town
    ExcellentHome/Apartment
    Airbnb
    From
    $51

Ashland Pet-Friendly Vacation Rentals

  • Comfortable, Private Guest Lodging
    ExcellentHome/Apartment
    Airbnb
    From
    $127
  • Oak Haven -Master Suite Bedroom
    ExcellentHome/Apartment
    Airbnb
    From
    $89
  • A relaxing country view home. Private yet close.
    Good4br Home/Apartment
    Airbnb
    From
    $441
  • Shady Grove Farm - Studio
    ExcellentHome/Apartment
    Airbnb
    From
    $96

Ashland Travel Guide

Ashland, Oregon is a small city in southern Oregon best known for hosting the Oregon Shakespeare Festival. The festival usually draws in around 400,000 guests to the city and performs a total of 11 plays on average, beginning every February.

Things to Do in Ashland

While the festival is a huge hit, there are plenty of other things to do while in Ashland. Head to Caldera’s Brewing Tap House and try some of the unique brews available. If you’re looking for nature, head to the Rogue River Valley for river rafting, fishing, hiking, and some of the prettiest views in the region. Other top parks include Lithia Park, Emigrant Lake, and Ashland Creek. ScienceWorks Museum and Garfield Park are top attractions for kids in Ashland. Ashland locals are reserved and may not go out of their way to greet you, but don’t let that fool you, the people in this town are kind natured and welcoming.

Best Time to Visit Ashland

The best time to visit is from February through November to catch some of the Oregon Shakespeare Festival.

Price and Availability in Ashland

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The cheapest day to stay at a vacation rental in Ashland tends to be Monday, while the most expensive day tends to be Friday. Vacation homes in Ashland tend to be busiest on Fridays, while it tends to be much quieter on Mondays.
The most expensive month to stay in a vacation rental in Ashland is in June, while the cheapest month is in December. The most popular time to book a vacation rental in Ashland is in the high season in July. Ashland has its low season in February, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Ashland

Rainy days
59° 23°
2
66° 26°
1
64° 21°
1
70° 20°
2
85° 24°
2
88° 34°
1
95° 38°
1
99° 41°
0
98° 42°
0
91° 34°
0
80° 29°
0
69° 18°
1
Dec
Jan
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May
Jun
Jul
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Sep
Oct
Nov
Rainy days

This climate histogram shows you the weather patterns in Ashland. The hottest month in Ashland is June, when temperatures peak at 99 ˚F. The coolest month is February, when temperatures drop to 18 ˚F. The wettest month in Ashland is January with 2.37 inches of rain, while the driest month is June with 0.04 inches of rain.

What Expert Travelers Think

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  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

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    BeckyKid World Citizen
  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide

Vacation Rentals in Ashland

Browse accommodations from all your favorite providers including Airbnb, Priceline, Bed and Breakfast and many more at AllTheRooms.com. Ashland has 1,545 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. If you are wanting to save money, the lowest priced place to stay in Ashland is just $15 per night. An average accommodation in Ashland costs on average $190 a night.

If you want an internet connection during your stay in Ashland, then you can choose from over 515 places to stay that have WiFi internet. 37 places to stay include a morning meal. Choose from 12 places to stay that provide gym facilities, so you don't miss a single workout. If you are driving to Ashland, you'll want to pick from 500 places to stay that provide parking. We have 59 hotels and vacation rentals that have a pool or jacuzzi.

AllTheRooms has 121 pet-friendly places to stay in Ashland, so if you're traveling with your cat or dog you won't have any problems.

In Ashland AllTheRooms currently compares hotels, vacation rentals, hostels from more than 4 providers, including 440 places to stay from Airbnb, 8 accommodations from Priceline and 8 places to stay from Bed and Breakfast.

781 of our accommodations in Ashland have been reviewed and rated. 72% are rated great. You can instantly book any of 467 places to stay right now.

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