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Ashland, OR Vacation Rentals

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Our Favorite Vacation Rentals in Ashland

  • The Pioneer House (South Suite) - Closest to OSF!
    The Pioneer House (South Suite) - Closest to OSF!
     
    Booking.comFrom $374
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  • Butler's Quarters~Downtown Ashland (Private Entry)
    Butler's Quarters~Downtown Ashland (Private Entry)
     
    HolidayLettingsFrom $205
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  • Bel Canto ~Stunning Views from Ashland’s Hillside
    Bel Canto ~Stunning Views from Ashland’s Hillside
     
    Booking.comFrom $190
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  • Hopyard View Farm ~ A Farm Experience in Ashland!
    Hopyard View Farm ~ A Farm Experience in Ashland!
     
    HolidayLettingsFrom $174
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  • Dream Cottage at Paschal Winery
    Dream Cottage at Paschal Winery
     
    Booking.comFrom $202
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  • 5 Star Delicious Home near Shakespeare
    5 Star Delicious Home near Shakespeare
    Good
    HolidayLettingsFrom $250
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  • Anderson Creek Barn Cottage - Minutes from Ashland
    Anderson Creek Barn Cottage - Minutes from Ashland
     
    Booking.comFrom $183
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  • Farmhouse Studio at Willow Witt Ranch
    Farmhouse Studio at Willow Witt Ranch
     
    HolidayLettingsFrom $286
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See all 1,276 deals in Ashland

Ashland Vacation Rentals with a Pool

  • Wood Hamlet - Picasso Suite by Downtown, w/kitchen
    Wood Hamlet - Picasso Suite by Downtown, w/kitchen
    Excellent
    AirbnbFrom $130
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See all deals in Ashland with a pool

Ashland Vacation Rentals with Wi-Fi

  • Maggie's Downtown Cottage
    Maggie's Downtown Cottage
    Excellent
    AirbnbFrom $179
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  • 2bd/1bth at Falcon Heights - wheelchair accessible
    2bd/1bth at Falcon Heights - wheelchair accessible
     
    AirbnbFrom $332
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  • Grenada Train Depot
    Grenada Train Depot
     
    AirbnbFrom $128
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  • The Ashland Farm Cabin
    The Ashland Farm Cabin
    Excellent
    AirbnbFrom $116
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See all deals in Ashland with WiFis

Ashland Pet-Friendly Vacation Rentals

  • Courtside Cottage~5-minute walk from OSF~Pet Friendly
    Courtside Cottage~5-minute walk from OSF~Pet Friendly
     
    HolidayLettingsFrom $275
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  • Carlisle Garden Suites - Calla Suite
    Carlisle Garden Suites - Calla Suite
    Excellent
    HolidayLettingsFrom $257
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  • Carlisle Garden Suites - Daisy Suite
    Carlisle Garden Suites - Daisy Suite
     
    HolidayLettingsFrom $257
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  • Carlisle Garden Suites - Iris Suite
    Carlisle Garden Suites - Iris Suite
     
    HolidayLettingsFrom $351
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See all deals in Ashland that allow pets

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 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 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 Weather in Ashland

95º 38º
0.61
99º 41º
0.04
98º 42º
0
91º 34º
0.37
80º 29º
0.39
69º 18º
1.46
59º 23º
2.37
66º 26º
1.33
64º 21º
0.76
70º 20º
1.62
85º 24º
2.28
88º 34º
1.06
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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 November, when temperatures drop to 18 ˚F. The wettest month in Ashland is December with 2.37 inches of rain, while the driest month is September with 0.37 inches of rain.

What Expert Travelers Think

Vacation Rentals in Ashland

At AllTheRooms.com we have rentals from all of the leading providers - Airbnb, Bed and Breakfast, Priceline and others. Ashland has 1,276 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, extravagant travelers and everything in between. If you are wanting to save money, the cheapest place to stay in Ashland is just $27 a night. The average price of an accommodation is around $191 per night.

If you have to have an internet connection during your stay in Ashland, then you can choose from over 464 places to stay that have WiFi internet. 30 of our accommodations include a breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 9 accommodations that have gyms. Driving to Ashland? Then choose one of the 439 places to stay that comes with a parking spot included. 44 places to stay have a a pool or jacuzzi

AllTheRooms has 102 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 349 places to stay from Airbnb, 6 accommodations from Bed and Breakfast and 6 places to stay from Priceline.

651 of the accommodations in Ashland have been reviewed by previous guests. They rated 66% as excellent or good. You can instantly book any of 363 places to stay right now.

Destinations near Ashland