Ashland holiday rentals

We found 297 holiday rentals — enter your dates for availability
Discover a selection of 107 homes, 58 apartments and other holiday rentals in Ashland that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a garden. Whatever you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Ashland

Showing deals for:6 Nov - 13 Nov

Living room
Pool
Front of house
Dining room
Exceptional
(35 reviews)

Come stay at our farmhouse! A place to integrate all the beauty surrounding you!

Ashland

8% off
S$7,713
for 7 nights, 1 room
S$1,102 per night
includes taxes & fees
Come stay at our farmhouse! A place to integrate all the beauty surrounding you!
Double Rainbow
Kitchen
Exterior
Kitchen
Exceptional
(129 reviews)

Tranquil setting surrounded by panoramic mountain views, grazing horses

Phoenix

11% off
S$1,313
for 7 nights, 1 cottage
S$188 per night
includes taxes & fees
Tranquil setting surrounded by panoramic mountain views, grazing horses
Outdoor dining
Private kitchen
Interior
Private kitchen
Wonderful
(7 reviews)

Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!

Ashland

15% off
S$1,850
for 7 nights, 1 home
S$264 per night
includes taxes & fees
Beautiful bungalow downtown Ashland railroad district, rv parking, adventure!
Exterior detail
Exterior
Living area
Room
Exceptional
(78 reviews)

Premier Downstairs Flat in Perfect Down Town Location

Ashland

16% off
S$2,556
for 7 nights, 1 home
S$365 per night
includes taxes & fees
Premier Downstairs Flat in Perfect Down Town Location
Private kitchen
Terrace/patio
Interior
Property grounds
Exceptional
(42 reviews)

Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland

Ashland

8% off
S$4,456
for 7 nights, 1 home
S$637 per night
includes taxes & fees
Second Spring Property - 3 bedroom 2 bath luxury home in the heart of Ashland
Living area
Dining
Room
Your friendly host(s) are often in the small cabin in case you need anything. :)
Exceptional
(9 reviews)

Gorgeous Lakeside BarnHOUSE + SAUNA!

Ashland

18% off
S$2,639
for 7 nights, 1 home
S$377 per night
includes taxes & fees
Gorgeous Lakeside BarnHOUSE + SAUNA!
Dining
Exterior
Private kitchen
Living area
Exceptional
(6 reviews)

ABBOTT'S COTTAGES - Falcon. 2 bedroom/2 bath within walking distance to downtown

Ashland

8% off
S$2,556
for 7 nights, 1 home
S$365 per night
includes taxes & fees
ABBOTT'S COTTAGES - Falcon. 2 bedroom/2 bath within walking distance to downtown
Titania kitchen
Oberon
Oberon entry
Titania kitchen
Exceptional
(129 reviews)

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Ashland

8% off
S$1,872
for 7 nights, 1 apartment
S$267 per night
includes taxes & fees
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Living area
Exterior detail
Outdoor dining
Room
Exceptional
(6 reviews)

ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown

Ashland

8% off
S$1,415
for 7 nights, 1 apartment
S$202 per night
includes taxes & fees
ABBOTT'S COTTAGES- The Egret. Studio cottage within walking distance of downtown
Primary bedroom
Living area
Interior
Exterior detail
Exceptional
(51 reviews)

East Main Downtown Bungalow

Ashland

15% off
S$1,469
for 7 nights, 1 home
S$210 per night
includes taxes & fees
East Main Downtown Bungalow
Dining
Primary bedroom
Private kitchen
Living area
Exceptional
(46 reviews)

New Downtown 3 Bedroom Upstairs Flat with views

Ashland

16% off
S$2,622
for 7 nights, 1 home
S$375 per night
includes taxes & fees
New Downtown 3 Bedroom Upstairs Flat with views
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The captivating area of Ashland awaits your stay

Enjoy the area's entertainment, theatre scene and opera with a rental holiday home in Ashland. Travellers to this welcoming city praise the festivals, gardens and cafes. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Ashland

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Ashland a fun place to get away to. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Mount Ashland Ski Area (7.8 mi / 12.5 km)
  • Centennial Golf Club (9.4 mi / 15.1 km)
  • Rogue Valley Country Club (10.6 mi / 17.1 km)
  • Weisinger Family Winery (3.5 mi / 5.6 km)
  • Paschal Winery (5 mi / 8.1 km)
  • EdenVale Winery (9.3 mi / 15 km)

Exploring the gardens and other natural features in Ashland

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Ashland is a great place to get outside. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Lithia Park (0.5 mi / 0.9 km)
  • Emigrant Lake (6.3 mi / 10.2 km)
  • Roxy Ann Peak and Prescott Park (11.4 mi / 18.3 km)
  • Howard Prairie Lake (16.1 mi / 26 km)
  • Applegate Lake (24.2 mi / 38.9 km)
  • Lake of the Woods (28 mi / 45.1 km)

Transport to and around Ashland

The nearest airport is in Medford, OR (MFR-Rogue Valley Intl.), located 14.4 mi (23.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Klamath Falls, OR (LMT-Klamath Falls Intl.), which is 49.7 mi (79.9 km) away.

Frequently asked questions

What is the best area to stay in Ashland when booking a holiday rental?
Historic Railroad District is one of the most sought-after neighbourhoods to book a holiday property in Ashland. Stay here to enjoy the convenience and privacy that comes with having the whole place to yourself.
What is the most popular type of holiday rental accommodation in Ashland?
Houses are the most popular kind of holiday rental in Ashland, according to our data. Even if you have a different vision in mind, Vrbo has properties in many sizes and shapes. Explore our options to find your perfect match.
How much does it cost to rent a holiday rental in Ashland?
Property type, season and length of stay are some factors that can determine the price of a holiday home. Simply add your travel dates to find your dream escape. From quaint country cottages to plush villas, all Vrbo holiday rentals provide amazing value.
How much does it cost to rent a beach house in Ashland?
Prices for beach houses in Ashland may vary depending on the size and style of the property and when you plan to travel. Simply enter your travel dates into Vrbo and the number of guests to see your options and prices. From there you can use our filter tool to refine your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday rentals in Ashland?
Yes, there are. You'll find 59 holiday homes that welcome pets in Ashland on Vrbo. Our furry friends need a break too, so simply use our search function for pet-friendly holiday rentals to find a property where Spot can lap up the good times.
What are popular rental amenities in Ashland?
Tennis, a barbecue grill and a firepit rank as the most popular rental amenities in Ashland. Whether you're planning to travel alone, with your sweetheart or a group of best friends, Vrbo will help you find a holiday rental that matches your tastes with all the features you'll enjoy.
Are there large group holiday rentals in Ashland?
Ashland has seven holiday rentals that can host 10 or more guests. These properties come with all the space you need to share good times with your favourite people.
Are there holiday rentals in Ashland that welcome kids?
With 59 family-friendly holiday homes to choose from in Ashland, now is the perfect time to introduce the kids to the wonders of travel. Simply click on our "Properties good for families" filter box to look for stays that feature conveniences perfect for holidaying families, like living rooms, yards, entertainment units and bunk beds.
What are the top attractions for families in Ashland?
Keep the kids entertained at these leading family-friendly attractions in Ashland:
  • ScienceWorks Hands-On Museum
  • Emigrant Lake
  • Bull Gap Lower Trailhead
Are there one-bedroom holiday rentals in Ashland?
Yes, there are 28 one-bedroom properties in Ashland to select from. A one-bedroom holiday home is a great choice if it's just the two of you or if you're flying solo. Toss in more space, convenience and privacy than a standard hotel, and you're sure to have an unforgettable getaway.
Can I find two-bedroom holiday rentals in Ashland?
Ashland has 12 two-bedroom holiday rentals to choose from. Find a holiday home with all the space and privacy you're looking for at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Ashland?
Ashland has nine holiday rentals with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to scrolling social media, these Vrbo homes make it easy to go online.
How can I find holiday rentals with air conditioning in Ashland?
Decide on your travel dates and then use our filters to look for holiday rentals with ac in Ashland on Vrbo. With 56 air-conditioned properties on offer here, you can look forward to a cool and comfortable trip.
How old do you have to be to rent a holiday rental in Ashland?
The minimum age is generally 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred Ashland holiday rental before booking.
How long can I rent a holiday rental in Ashland for?
It all depends on the Ashland property. To see a list of options offering extended stays, just type your dates and number of guests into the Vrbo search page. Enjoy having the place to yourself, along with comforts such as air conditioning, a kitchen and a yard to run around in. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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