Destination Photo

Ashland, OR Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. Oregon
  4. Ashland

Our Favorite Vacation Rentals in Ashland

  • Anne Hathaway House
    Anne Hathaway House
     Home/Apartment
    Booking.comFrom $570
    View Deal
  • De Launay House
    De Launay House
    Excellent6br Home/Apartment
    HolidayLettingsFrom $965
    View Deal
  • Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF
    Blue Moon Cottage ~ Pet Friendly ~ 5 Blocks to OSF
     Home/Apartment
    Booking.comFrom $259
    View Deal
  • Hopyard View Farm ~ A Farm Experience in Ashland!
    Hopyard View Farm ~ A Farm Experience in Ashland!
     2br Farm Stay
    HolidayLettingsFrom $194
    View Deal
  • Dream Cottage at Paschal Winery
    Dream Cottage at Paschal Winery
     Home/Apartment
    Booking.comFrom $202
    View Deal
  • 5 Star Delicious Home near Shakespeare
    5 Star Delicious Home near Shakespeare
    Good3br Home/Apartment
    HolidayLettingsFrom $250
    View Deal
  • Anderson Creek Barn Cottage - Minutes from Ashland
    Anderson Creek Barn Cottage - Minutes from Ashland
     Home/Apartment
    Booking.comFrom $183
    View Deal
  • Valley View Cottage~Short Drive to Medford/Ashland
    Valley View Cottage~Short Drive to Medford/Ashland
     1br Home/Apartment
    HolidayLettingsFrom $191
    View Deal
See all 1,331 deals in Ashland

Ashland Vacation Rentals with Wi-Fi

  • Porscha's Hideaway Italian Upscale
    Porscha's Hideaway Italian Upscale
    ExcellentHome/Apartment
    AirbnbFrom $234
    View Deal
  • Grenada Train Depot
    Grenada Train Depot
    GoodHome/Apartment
    AirbnbFrom $129
    View Deal
  • The Ashland Farm Cabin
    The Ashland Farm Cabin
    Excellent1br Home/Apartment
    AirbnbFrom $115
    View Deal
  • Coyote Moon
    Coyote Moon
    Excellent2br Home/Apartment
    AirbnbFrom $254
    View Deal
See all deals in Ashland with WiFis

Ashland Pet-Friendly Vacation Rentals

  • Pelton Villa
    Pelton Villa
    Excellent4br Home/Apartment
    HolidayLettingsFrom $468
    View Deal
  • Hound's Landing Cottage #A ~ A dog's walk to OSF
    Hound's Landing Cottage #A ~ A dog's walk to OSF
     2br Home/Apartment
    HolidayLettingsFrom $325
    View Deal
  • Anderson Creek Barn Cottage - Minutes from Ashland - Pet Friendly
    Anderson Creek Barn Cottage - Minutes from Ashland - Pet Friendly
     1br Home/Apartment
    HolidayLettingsFrom $219
    View Deal
  • Garden Suite
    Garden Suite
    Excellent2br Home/Apartment
    AirbnbFrom $283
    View Deal
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

Most expensive
Most availability
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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

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
95º 38º
0.61
99º 41º
0.04
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Rainy days
This climate histogram shows you the weather patterns in Ashland. The warmest months in Ashland are June and May, when temperatures reach 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 many more. Ashland has 1,331 hotels, vacation rentals and other special places to stay, with prices to suit careful travellers, luxury travelers and everything in between. For those trying to save money, the lowest priced place to stay in Ashland is just $18 per night. A typical vacation rental in Ashland costs on average $198 a night.

If you need an internet connection during your time in Ashland, then you can choose from over 513 places to stay that have WiFi internet. We have 32 accommodations that come with breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 11 accommodations that have gym facilities. If you are driving to Ashland, you'll want to pick from 487 places to stay that provide parking. We track 48 vacation rentals that have a pool or jacuzzi.

AllTheRooms has 116 pet-friendly places to stay in Ashland, so if you're traveling with your pet you won't have any problems.

In Ashland AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 4 providers, including 402 places to stay from Airbnb, 6 accommodations from Bed and Breakfast and 6 places to stay from Priceline.

722 accommodations in Ashland have been reviewed; 69% are rated excellent or good. 436 places to stay in are instantly bookable.

Destinations near Ashland