Ashland, OR Vacation Rentals

Our Favorite Vacation Rentals in Ashland

  • 'C' Street Station - Short walk to OSF
     Home/Apartment
    Booking.com
    From
    $172
  • Spur Rail Loft House~ Just a few blocks to Downtown Ashland
     3br Country House
    HolidayLettings
    From
    $340
  • Lori Lanes 'Juliet Cottage' ~ 2 Bedroom ~ Downtown
     Home/Apartment
    Booking.com
    From
    $225
  • Art & Garden Cottage ~ Near Downtown ~ Pet Friendly
     Cottage
    HolidayLettings
    From
    $197
  • Bel Canto ~Stunning Views from Ashland’s Hillside
     Country House
    Booking.com
    From
    $190
  • 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

Check prices for these upcoming dates

Ashland Vacation Rentals with a Pool

  • Deluxe Garden Studio
    ExcellentHome/Apartment
    Airbnb
    From
    $137
  • Pool table, Pool, Huge house! 5 queen bdrms!
    Excellent5br Home/Apartment
    Airbnb
    From
    $267
  • Angel Crest Guest Suite - East Medford Hills
    ExcellentHome/Apartment
    Airbnb
    From
    $86
  • Ashland Carter House, Carriage House!
    ExcellentHome/Apartment
    Airbnb
    From
    $180

Ashland Vacation Rentals with Wi-Fi

  • Auburn Street Cottage in Ashland
    ExcellentHome/Apartment
    Airbnb
    From
    $184
  • Cozy camping close to town
    ExcellentHome/Apartment
    Airbnb
    From
    $52
  • Charming very well appointed cottage !
    ExcellentHome/Apartment
    Airbnb
    From
    $184
  • Cozy Private Guest Suite with Incredible View
    GoodHome/Apartment
    Airbnb
    From
    $136

Ashland Pet-Friendly Vacation Rentals

  • 5 Star Delicious Home near Shakespeare
    Good3br Home/Apartment
    HolidayLettings
    From
    $250
  • 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

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
62° 19°
2
58° 19°
4
74° 23°
1
81° 30°
4
87° 31°
2
96° 35°
0
92° 45°
0
99° 45°
1
91° 31°
2
74° 21°
0
70° 21°
0
59° 19°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Ashland. The warmest months in Ashland are May and July, when temperatures reach 99 ˚F. The coolest month is January, when temperatures drop to 19 ˚F. The wettest month in Ashland is November with 4.18 inches of rain, while the driest month is October with 1.17 inches of rain.

What Expert Travelers Think

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    Max HobbsLTL Mandarin School
  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

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    JazThe Life of a Social Butterfly
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Vacation Rentals in Ashland

Browse rentals from all your favorite providers including Airbnb, Priceline, Agoda and more at AllTheRooms.com. Ashland has 1,265 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those trying to save money, the cheapest place to stay in Ashland is just $18 per night. The average price of a rental is around $184 per night.

Those looking to get some work done during their trip to Ashland can choose from 453 places to stay that provide WiFi. 39 of our accommodations come with breakfast in the price. You can keep up with your workout routine by staying at one of 11 accommodations that provide gym facilities. Driving to Ashland? Then choose one of the 454 places to stay that comes with a parking spot included. 55 hotels and vacation rentals have a a pool or jacuzzi

If you're traveling with your best friend, then make sure to choose one of the 103 pet-friendly accommodations available.

In Ashland AllTheRooms currently compares hotels, vacation rentals, hostels from more than 3 providers, including 414 places to stay from Airbnb, 5 accommodations from Priceline and 5 places to stay from Agoda.

687 of the accommodations in Ashland have been reviewed by previous guests. They rated 74% as excellent or good. 441 places to stay in are instantly bookable.

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