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Ashland Vacation Rentals

Find 561 available offers from 5 partners
Ashland
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Cabin
House
Apartment
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

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.

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Best Vacation Home Deals in Ashland

Save up to 27%

Apartment Ashland
Dec 9 - Dec 16
-26%
$176
$131 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Rental Apartment in Ashland with Yard
4.9
Outstanding (94 ratings)
Ashland, Jackson County, Oregon, United States
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Cottage Ashland
Sep 14 - Sep 21
-18%
$400
$330 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in Ashland with Private Parking
4.5
Excellent (14 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Jan 20 - Jan 27
-27%
$220
$162 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Ashland with Grill & Yard
5.0
Outstanding (12 ratings)
Ashland, Jackson County, Oregon, United States
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Compare and find a dreamlike property from $72 per night by searching and comparing the 561 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 66%.

Top-Rated Rentals and Accommodations in Ashland

Book Vacation Rental Offers with the Highest User Rating

House Ashland
Jan 20 - Jan 27
-32%
$502
$344 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Ashland with Private Parking + Mountain Views
4.7
Excellent (109 ratings)
Ashland, Jackson County, Oregon, United States
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Apartment Ashland
Jul 6 - Jul 13
$135 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Ashland with Grill & Yard + Canyon View
5.0
Outstanding (94 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Sep 14 - Sep 21
$395 per night
House ∙ 10 guests ∙ 3 bedrooms
Charming House in Ashland with Grill & Yard
4.8
Outstanding (59 ratings)
Ashland, Jackson County, Oregon, United States
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Recommended Vacation Rentals in Ashland

Find your perfect vacation rental in Ashland: from $72 per night

House Ashland
Jun 1 - Jun 8
$180 per night
House ∙ 4 guests ∙ 2 bedrooms
Pleasant Vacation Home in Ashland + Mountain Views
5.0
Outstanding (100 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Jan 20 - Jan 27
$275 per night
House ∙ 7 guests ∙ 3 bedrooms
Vacation Home in Ashland
4.8
Outstanding (21 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Sep 14 - Sep 21
$428 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Ashland with Grill
5.0
Outstanding (48 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Jun 1 - Jun 8
$149 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Ashland with Yard + Mountain Views
5.0
Outstanding (87 ratings)
Ashland, Jackson County, Oregon, United States
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Farmhouse Ashland
Nov 4 - Nov 11
$792 per night
Farmhouse ∙ 10 guests ∙ 4 bedrooms
Farm in Ashland with Japanese Garden + Gorgeous Views
5.0
Outstanding (10 ratings)
Ashland, Jackson County, Oregon, United States
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Apartment Ashland
Nov 11 - Nov 18
$153 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Apartment in Ashland
4.8
Outstanding (122 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Mar 23 - Mar 30
$268 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Ashland
5.0
Outstanding (46 ratings)
Ashland, Jackson County, Oregon, United States
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Cottage Ashland
Jan 20 - Jan 27
$150 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Cottage in Ashland with Yard
4.9
Outstanding (19 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Jun 22 - Jun 29
$189 per night
House ∙ 3 guests ∙ 1 bedroom
House in Ashland with Yard
4.9
Outstanding (54 ratings)
Ashland, Jackson County, Oregon, United States
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Budget-friendly Vacation Rentals in Ashland

Find Fantastic yet Inexpensive Offers

House Ashland
Aug 11 - Aug 18
$208 per night
House ∙ 6 guests ∙ 3 bedrooms
Lovely House in Ashland + Great View
5.0
Outstanding (24 ratings)
Ashland, Jackson County, Oregon, United States
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Cottage Ashland
Oct 21 - Oct 28
$147 per night
Cottage ∙ 3 guests ∙ 1 bedroom
Private Cottage in Ashland with Private Garden
4.9
Outstanding (29 ratings)
Ashland, Jackson County, Oregon, United States
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House Ashland
Dec 23 - Dec 30
$299 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Ashland with Grill & Yard
4.9
Outstanding (77 ratings)
Ashland, Jackson County, Oregon, United States
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Ashland rental with full kitchen.

House  Ashland
Dec 23 - Dec 30
$395 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming Vacation Home in Ashland with Yard
5.0
Outstanding (32 ratings)
Ashland, Jackson County, Oregon, United States
Kitchen
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Cottage  Ashland
Dec 16 - Dec 23
-16%
$171
$144 per night
Cottage ∙ 3 guests ∙ 1 bedroom
Pleasant Cottage in Ashland with Yard & Grill
5.0
Outstanding (176 ratings)
Ashland, Jackson County, Oregon, United States
Kitchen
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Bed and breakfast  Ashland
Mar 23 - Mar 30
-45%
$400
$220 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
Lovely Bed And Breakfast in Ashland with Patio & Yard
4.9
Outstanding (58 ratings)
Ashland, Jackson County, Oregon, United States
Kitchen
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights in Ashland by booking a vacation home with a fireplace.

Bed and breakfast  Ashland
Sep 30 - Oct 7
-37%
$600
$378 per night
Bed and breakfast ∙ 3 guests ∙ 1 bedroom
Bed And Breakfast in Ashland with Pool, Patio & Yard
5.0
Outstanding (8 ratings)
Ashland, Jackson County, Oregon, United States
Fireplace
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Bed and breakfast  Ashland
Mar 23 - Mar 30
$362 per night
Bed and breakfast ∙ 2 guests ∙ 1 bedroom
B&B in Ashland with Yard
4.9
Outstanding (266 ratings)
Ashland, Jackson County, Oregon, United States
Fireplace
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Bed and breakfast  Ashland
Mar 23 - Mar 30
$202 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
B&B in Ashland with Yard & Patio
Ashland, Jackson County, Oregon, United States
Fireplace
Details
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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Ashland accommodation with high-speed internet.

House  Ashland
Sep 30 - Oct 7
$333 per night
House ∙ 9 guests ∙ 4 bedrooms
Charming Vacation Home in Ashland with Yard
5.0
Outstanding (1 rating)
Ashland, Jackson County, Oregon, United States
Internet
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Cottage  Ashland
Oct 13 - Oct 20
$125 per night
Cottage ∙ 2 guests ∙ 1 bedroom
Cottage in Ashland with Vegetable Garden
Ashland, Jackson County, Oregon, United States
Internet
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Bed and breakfast  Ashland
Dec 23 - Dec 30
-22%
$181
$142 per night
Bed and breakfast ∙ 4 guests ∙ 1 bedroom
Bed & Breakfast in Ashland with Patio, Yard & Pool
Ashland, Jackson County, Oregon, United States
Free cancellation
Internet
Details
Expedia
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Popular Rental Amenities in Ashland

  • Pet-friendly (57)
  • WiFi (499)
  • Kitchen (204)
  • Pool (228)
  • TV (436)
  • Fireplace (114)
  • Hot tub (66)
  • Balcony/patio (199)
  • No smoking (346)
  • Yard (336)
  • Washing machine (148)
  • Air conditioning (486)

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 "Pets allowed" or "Internet," which makes it a fantastic vacation destination if you travel with your pet or you can't imagine a vacation without internet. Three features that are not common are "Fenced," "Sauna," and "Crib."

The Weather in Ashland

max.
Min.
48°
30°
15 days 15
max.
Min.
55°
36°
14 days 14
max.
Min.
61°
39°
17 days 17
max.
Min.
68°
43°
13 days 13
max.
Min.
77°
48°
9 days 9
max.
Min.
84°
54°
6 days 6
max.
Min.
93°
61°
2 days 2
max.
Min.
93°
59°
3 days 3
max.
Min.
84°
52°
5 days 5
max.
Min.
72°
45°
11 days 11
max.
Min.
55°
37°
15 days 15
max.
Min.
45°
32°
20 days 20
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

You can see our climate diagram above. During July, maximum temperatures go up to more than 93° However, temperatures can go lower than 30° in Ashland in January. The rainiest month is December while the driest month is July.

7-Day Weather Forecast in Ashland

Sun, 24 Sep
53°
51°

15%

0 h

5 mi/h

Mon, 25 Sep
57°
53°

15%

0 h

11 mi/h

Tue, 26 Sep
59°
50°

15%

1 h

3 mi/h

Wed, 27 Sep
68°
48°

0%

11 h

5 mi/h

Thu, 28 Sep
75°
53°

10%

9 h

6 mi/h

Fri, 29 Sep
62°
46°

15%

2 h

8 mi/h

Sat, 30 Sep
64°
46°

0%

8 h

5 mi/h

Accommodations for your vacation in Ashland

Users who are searching for house rental 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 $483 a night, with an average area of 142 m². Furthermore, this specific type of lodging is ideal for large groups, as the majority of house rental can welcome groups of 7. If you would like to rent something else, you can search many other offers, such as bed and breakfast rental, which are another typical property type in Ashland. Bed and breakfast rental in Ashland are 24 m² on average, with average prices of $325 a night.
Where to find the best food in Ashland?

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!

Where are the unique attractions in Ashland?

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.

What are the best events and festivals in Ashland?

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.

Information about vacation rentals in Ashland

🏡 Vacation rentals available 561 homes
💳 Possible discounts up to 66%
🌙 Nightly prices starting at $72
⭐ Popular amenities Pets allowed, Internet and Kitchen
🐾 Pet friendly homes 67 homes
🏊 Vacation rentals with pools 230 homes

Frequently Asked Questions

What is the price per night for a vacation rental in Ashland?

The average accommodation in Ashland is priced at $72 per night. If you’re interested in a house rental, the average price is $483 per night. A bed and breakfast rental Ashland will cost $325 per night on average.

How many vacation homes are available to book in Ashland?

There are currently 561 vacation homes to choose from for your vacation.

What are the most popular amenities for vacation homes in Ashland?

Most travelers search for Pets allowed, Internet, and Kitchen when booking a vacation rental in Ashland.

How many vacation homes with pools are in Ashland?

Ashland offers 230 Hotel room and Motel options available for booking.

Are dogs allowed in vacation rentals in Ashland?

Finding a vacation home in Ashland that allows pets is definitely possible, with 67 pet-friendly available.

What's the best month to travel to Ashland?

The warmest months in Ashland are July and August, with temperatures around 93 °F. The coldest months in Ashland are January and December, with 30 °F on average.

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