Ashland Vacation Rentals

Compare 394 available properties from 16 providers
Ashland
Save up to 24%

Best Vacation Home Deals in Ashland

-17%
e.g. 9/18 - 9/25
House ∙ 4 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $279 $336
VRBO
4.9
View deal
-18%
e.g. 12/8 - 12/15
Apartment ∙ 4 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $155 $189
VRBO
5.0
View deal
-24%
e.g. 11/3 - 11/10
House ∙ 6 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $294 $387
VRBO
5.0
View deal

Compare and find a dreamlike property from $55 per night by searching and comparing the 368 properties listed in Ashland. With HomeToGo, you can instantly search and compare the offers of each available property to find the best price and save up to 24%.

Recommended Vacation Rentals in Ashland

Rent a vacation accommodation in Ashland: from $55 per night

House ∙ 4 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $104
VRBO
4.7
View deal
House ∙ 4 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $244
VRBO
5.0
View deal
House ∙ 4 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $244
VRBO
4.0
View deal
House ∙ 4 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $227
VRBO
4.9
View deal
Apartment ∙ 6 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $79
VRBO
4.7
View deal
House ∙ 2 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $238
VRBO
4.0
View deal
House ∙ 4 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $176
VRBO
4.5
View deal
Motel ∙ 4 guests
Ashland, Jackson County, Oregon, United States
from $84
Booking.com
4.1
View deal
See all offers

Vacation Homes With Fishing Spots Nearby

Fishing
Apartment ∙ 2 guests
Ashland, Jackson County, Oregon, United States
from $153
VRBO
4.9
View deal
Fishing
House ∙ 4 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $279
VRBO
4.9
View deal
Fishing
Apartment ∙ 4 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $155
VRBO
5.0
View deal
Fishing
Apartment ∙ 3 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $119
VRBO
4.9
View deal
See all offers

Apartments With a Balcony or Patio

Balcony/Patio
House ∙ 4 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $97
VRBO
4.7
View deal
Balcony/Patio
Apartment ∙ 3 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $179
VRBO
4.9
View deal
Balcony/Patio
Apartment ∙ 5 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $79
VRBO
4.6
View deal
Balcony/Patio
House ∙ 4 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $224
VRBO
5.0
View deal
See all offers

Vacation Rentals With a Fireplace

Fireplace
House ∙ 4 guests ∙ 1 bedroom
Ashland, Jackson County, Oregon, United States
from $195
VRBO
5.0
View deal
Fireplace
House ∙ 4 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $179
VRBO
5.0
View deal
Fireplace
House ∙ 8 guests ∙ 3 bedrooms
Ashland, Jackson County, Oregon, United States
from $378
VRBO
5.0
View deal
Fireplace
House ∙ 6 guests ∙ 2 bedrooms
Ashland, Jackson County, Oregon, United States
from $159
VRBO
5.0
View deal
See all offers

Popular Rental Amenities in Ashland

  • Internet (326)
  • No smoking (321)
  • Parking (315)
  • Kitchen (271)
  • AC (265)
  • TV (239)
  • Microwave (218)
  • No pets (172)
  • Yard (157)
  • Balcony/Patio (133)
  • Grill (113)
  • Dishwasher (105)
Properties can be chosen based on the amenities they offer. Above, you will find the number of properties that provide a specific amenity in Ashland. Most of the vacation rentals in Ashland provide "internet" or "TVs," which makes it a fantastic vacation destination if you need internet access during your vacation or you want to tune out with some TV time. Three features that are not common are "saunas," "Jacuzzis," and "fireplaces."

Price and Availability Index Ashland

Vacation Rental Price Information in Ashland

The price graph will give you the nightly price average for the upcoming months of the year. The week with the highest average prices is in July (7/21 - 7/28). During this week, a night will cost on average $246. However, in December (12/22 - 12/29), prices decrease to an average of $200 per night.

Rental Availability Information in Ashland

Check how busy Ashland is with our availability graph. The week with the least available rentals is in July (7/28 - 8/4), with only 58% of the rentals available. It is easier to find a rental in a week of April (4/27 - 5/4), as only 10% of the accommodations are booked.

The Weather in Ashland

48°
30°
55°
36°
61°
39°
68°
43°
77°
48°
84°
54°
93°
61°
93°
59°
84°
52°
72°
45°
55°
37°
45°
32°
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for Ashland. During July, maximum temperatures go up to more than 93° No heat wave is expected in January, where minimum average temperatures usally hit a 30° low. December is the wettest month.

Users who are searching for house rentals in Ashland have plenty of choices, as they are the most common property type in this destination. Interestingly, specific accommodation type, this type of property in particular is $289 a night, with an average area of 1,060 ft². Furthermore, this specific type of lodging is ideal for medium-sized groups and families, as the majority of house rentals can welcome groups of 6. If you would like to rent something else, you can search many other offers, such as apartment rentals, which are another typical property type in Ashland. Apartment rentals in Ashland are 700 ft² on average, with average prices of $245 a night.

Your getaway vacation home awaits you in beautiful Ashland

Ashland boasts an array of vacation rentals ranging from quaint cottages and apartments to spacious and beautiful Victorian houses and modern homes with full amenities. For nature buffs, choose a vacation rental on the outskirts of the city limits in a chalet – or even a renovated barn.

Show all 394 properties
Food & Drinks

Flavors for all palates

Ashland's East Main Street and Siskiyou Boulevard offer many eateries within quick walking distance. For breakfast, try the lemon ricotta stuffed French toast at Morning Glory Cafe. For brunch, skip on over to Brothers' Restaurant for a Mediterranean grilled cheese sandwich and an organic lemonade. In the evening, stroll to Alchemy Restaurant and Bar and order the scallop and cockles with a craft cocktail like "A Date with the Night". You won't regret it!

Local Attractions

Excursions and activities for everyone

Situated in the bio diverse Siskiyou Mountain Range at the southern tip of the fertile Rogue Valley, Ashland naturally offers a wide range of activities for all ages. Spend your day skiing and playing in the snow on nearby Mount Ashland at the first certified sustainable ski resort Mt. Ashland Ski Area. Go white water rafting or horseback riding just minutes from the town center. Rent a mountain bike and ride a loop on Ashland's scenic Lithia Park Trail. For wine tasters and connoisseurs, take a wine and artisan food tour in a 20 mile radius of beautiful foothill and valley landscape.

Local Events

Shakespeare galore

Last but not least, and without further ado – Shakespeare! Yes, your Ashland vacation getaway will be complete when you take in at least one live theatrical production of the renowned Oregon Shakespeare Festival. Started in 1935 and boasting hundreds of productions since its inception, the Oregon Shakespeare Festival has evolved to offer theater-goers crème de la crème actors and encore performances. Book ahead of time for the annual February-November season and enjoy live, quality theater practically at your vacation house doorstep.

We compare more than 300 providers, including:

Booking.com Vacation Rentals in Ashland VRBO Vacation Rentals in Ashland HomeAway Vacation Rentals in Ashland TripAdvisor Vacation Rentals in Ashland VacationRentals.com Vacation Rentals in Ashland HouseTrip Vacation Rentals in Ashland FlipKey Vacation Rentals in Ashland Wimdu Vacation Rentals in Ashland 9flats.com Vacation Rentals in Ashland VaycayHero Vacation Rentals in Ashland PerfectPlaces.com Vacation Rentals in Ashland Homestay.com Vacation Rentals in Ashland only-apartments Vacation Rentals in Ashland Interhome Vacation Rentals in Ashland Bedycasa Vacation Rentals in Ashland Novasol Vacation Rentals in Ashland HomeEscape Vacation Rentals in Ashland

Vacation Destinations Near Ashland