Ashland, OR Vacation Rentals

Our Favorite Vacation Rentals in Ashland

  • 'C' Street Station - Short walk to OSF
     Home/Apartment
    Booking.com
    From
    $190
  • Perfect vacation cottage
    Excellent2br Cottage
    HolidayLettings
    From
    $412
  • Art & Garden Cottage ~ Near Downtown
     Home/Apartment
    Booking.com
    From
    $156
  • Hopyard View Farm ~ A Farm Experience in Ashland!
     2br Farm Stay
    HolidayLettings
    From
    $194
  • Dream Cottage at Paschal Winery
     Home/Apartment
    Booking.com
    From
    $202
  • Cattle View Ranch House
     4br Home/Apartment
    HolidayLettings
    From
    $486
  • Anderson Creek Barn Cottage - Minutes from Ashland
     Home/Apartment
    Booking.com
    From
    $183
  • 5 Star Delicious Home near Shakespeare
    Good3br Home/Apartment
    HolidayLettings
    From
    $250

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
    $356
  • Angel Crest Guest Suite - East Medford Hills
    ExcellentHome/Apartment
    Airbnb
    From
    $76

Ashland Vacation Rentals with Wi-Fi

  • Auburn Street Cottage in Ashland
    ExcellentHome/Apartment
    Airbnb
    From
    $184
  • Porscha's Hideaway Italian Upscale
    ExcellentHome/Apartment
    Airbnb
    From
    $234
  • Grenada Train Depot
    GoodHome/Apartment
    Airbnb
    From
    $129
  • The Ashland Farm Cabin
    ExcellentHome/Apartment
    Airbnb
    From
    $115

Ashland Pet-Friendly Vacation Rentals

  • Carlisle Garden Suites - Viola Suite
    NiceCottage
    HolidayLettings
    From
    $257
  • Carlisle Garden Suites - Calla Suite
    OkayCottage
    HolidayLettings
    From
    $257
  • Carlisle Garden Suites - Daisy Suite
     Cottage
    HolidayLettings
    From
    $257
  • Carlisle Garden Suites - Iris Suite
     Cottage
    HolidayLettings
    From
    $351

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

Most expensive
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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
80° 29°
0
69° 18°
1
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
Oct
Nov
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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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    JazThe Life of a Social Butterfly
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Vacation Rentals in Ashland

Find the perfect vacation rental for your vacation at AllTheRooms.com. We compare Airbnb, Bed and Breakfast, Priceline and more. AllTheRooms has 1,416 vacation rentals, hotels and other great places to stay during your time in Ashland, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. For those traveling on a budget, the cheapest place to stay in Ashland is available at $15 per night. On average, an accommodation in Ashland will cost you $194 per night.

Those needing to get some work done during their trip to Ashland can pick from 527 places to stay that include WiFi. 34 of our accommodations come with breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 11 accommodations that have gyms. If you are driving to Ashland, you'll want to pick from 504 places to stay that provide parking. 48 hotels and vacation rentals have a a pool or jacuzzi

Those traveling with a cat, dog or some other animal can stay in any of 116 accommodations that are designated as pet-friendly.

AllTheRooms aggregates vacation rentals, hotels and other bespoke accommodation types from many providers in Ashland, including 417 places to stay from Airbnb, 8 accommodations from Bed and Breakfast and 6 places to stay from Priceline

769 of our accommodations in Ashland have been rated by previous guests. They rated 72% as great. 443 accommodations allow instant booking.

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