Ashland holiday rentals

We found 305 holiday rentals — enter your dates for availability
Discover a selection of 108 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:30 Oct - 6 Nov

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Why visit Ashland

  • Vibrant Arts Scene: Experience the renowned Oregon Shakespeare Festival, showcasing exceptional theatrical performances in a charming setting.
  • Beautiful Parks: Explore picturesque Lithia Park, offering scenic trails, tranquil lakes, and lush gardens ideal for leisurely strolls.
  • Outdoor Activities: Engage in various outdoor adventures, from hiking and biking to exploring nearby state parks and natural landscapes.
  • Charming Downtown: Enjoy the quaint streets filled with unique shops, local eateries, and a friendly atmosphere that enhances your visit.
  • Welcoming Accommodations: Settle into comfortable lodgings that offer a range of amenities, ensuring a delightful stay in Ashland.

Popular types of accommodation in Ashland

As you plan your visit to Ashland, Oregon, immerse yourself in a city renowned for its vibrant arts scene and stunning natural beauty. Delight in friendly accommodations, from stylish private holiday homes to charming cottages and apartments. Enjoy hotel amenities that enhance your stay, including delightful breakfast options and well-appointed guestrooms. Explore local attractions, such as the celebrated Oregon Shakespeare Festival and picturesque Lithia Park, making your holiday an unforgettable experience.

  • Private Holiday Homes: The top choice for visitors, offering spacious and comfortable living for families and groups.
  • Cottages: A delightful option for a quaint and picturesque stay, ideal for couples or small families.
  • Apartments: A convenient and flexible choice, perfect for those seeking urban amenities and easy access to local attractions.
  • Cabins: A rustic and charming retreat, providing a serene escape for nature enthusiasts.
  • Chalets: A unique accommodation type that combines comfort and alpine charm, great for a relaxing getaway.**

Top attractions in Ashland

Ashland, Oregon, United States of America is a charming city offering a blend of outdoor adventures and cultural experiences. Visitors can explore scenic lakes, urban parks, and national or state parks, all located within the city. Enjoy the natural beauty and rich heritage of Ashland through its diverse attractions and engaging local experiences, making it an ideal destination for an adventurous and culturally immersive holiday.

  • Tashi Choling Buddhist Center: Nestled in Ashland, this temple radiates a rich cultural ambience, offering visitors a serene escape with traditional Buddhist practices and meditation sessions.
  • Lithia Park: An urban oasis in the heart of Ashland, perfect for family outings, leisurely strolls, and picnics amidst beautifully landscaped gardens and vibrant city life.
  • Howard Prairie Lake: A picturesque lake with a hint of romance, ideal for outdoor enthusiasts seeking scenic views and leisurely beachside moments.

Things to do recommended for couples

For a romantic getaway in Ashland, explore the enchanting Lithia Park with its serene landscapes, or enjoy a delightful wine tasting at local vineyards. Don't miss an evening at the Oregon Shakespeare Festival, immersing yourselves in captivating performances under the stars.

Things to do recommended for families

Families visiting Ashland can explore the enchanting Lithia Park, perfect for picnics and play. Enjoy the Oregon Shakespeare Festival, which offers family-friendly performances, and visit the ScienceWorks Hands-On Museum for interactive exhibits that are sure to engage children of all ages.

Things to do recommended for groups

Experience the thrill of motor racing at Champion Raceway, located 26km from Ashland. This exciting venue offers an adrenaline-filled adventure for your group, perfect for those seeking a sporty atmosphere and unforgettable memories.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Ashland

If you're travelling with a group, as a family, bringing your pets, or seeking longer stays, be sure to set your filters according to your key priorities. Here are some helpful Stayz booking tips for you.

  • Traveling to Ashland with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Stayz.
  • Traveling to Ashland with young kids: Travelling with young children can present its own set of challenges. It is essential to prioritise their comfort and safety, as well as to seek out age-appropriate facilities, like a private swimming pool. Additionally, it’s wise to think about your closeness to attractions that are suitable for families.
  • Taking your pets with you to Ashland: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ashland: If you're seeking holiday rentals with great offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Ashland

Discover Ashland's charming downtown, where scenic views and adventure await. Stroll through its quaint streets and indulge in the local culture, with friendly locals and a vibrant atmosphere. Perfect for outdoor enthusiasts, Ashland offers a romantic and family-friendly setting, ensuring a memorable holiday experience.

  • Historic Railroad District: Nestled within the Ashland area, the Historic Railroad District offers travellers a delightful blend of outdoor pursuits and scenic vistas paired with a romantic ambience. The neighbourhood is characterised by its close proximity to renowned theatre venues, invigorating hiking trails and educational opportunities. Visitors can revel in the beauty of a nearby lake, explore expansive national state parks and immerse themselves in the wonders of a national park, all of which contribute to a rich and varied travel experience.
  • Historic Downtown District: Situated in the heart of Ashland, the Historic Downtown District is celebrated for its romantic allure, outdoor charm and family-friendly attractions. This neighbourhood boasts access to stimulating theatre performances, engaging educational experiences and picturesque hiking trails. The local landmarks include a serene lake, a sprawling national state park and a majestic national park, ensuring that each visit is filled with memorable encounters and cultural enrichment.
  • Talent: Located 8km from Ashland, Talent is a vibrant city offering an adventurous escape with its scenic and outdoor attractions. This locale provides a mix of recreational areas, theatre venues and invigorating hiking trails, making it an ideal destination for those seeking active pursuits. With attractions such as a captivating lake, a national state park and a meandering river, Talent promises a diverse and exhilarating travel experience for every explorer.

Best time to go to Ashland

If you're planning a trip to Ashland, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January36.3°F (2.4°C)Light RainMostly SunnyAverageSlightly Low
February37.2°F (2.9°C)Light RainMostly SunnyAverageSlightly Low
March40.5°F (4.7°C)Light RainMostly SunnyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May53.2°F (11.8°C)Light RainMostly SunnyAverageAverage
June60.4°F (15.8°C)No Rain (Dry)Mostly SunnySlightly HighSlightly High
July69.3°F (20.7°C)No Rain (Dry)SunnySlightly HighSlightly High
August68.7°F (20.4°C)No Rain (Dry)SunnyAverageSlightly High
September61.5°F (16.4°C)No Rain (Dry)SunnyAverageAverage
October51.1°F (10.6°C)Light RainMostly SunnySlightly LowAverage
November40.8°F (4.9°C)Light RainMostly SunnySlightly LowAverage
December34.7°F (1.5°C)Light RainMostly SunnySlightly LowAverage

Booking with Stayz is simple

Are you aiming to save some money on your upcoming travels? It’s worth being flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Stayz property within your budget, please utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz's Trip Board offers a handy platform for you to plan new journeys, resume your previous arrangements, or manage your itinerary. You'll discover your saved or booked properties neatly organised under Potential, Upcoming, or Current Trips. To begin utilising Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.

The information above was last updated:

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)
  • North Mountain Park (0.7 mi / 1.2 km)
  • Emigrant Lake (6.3 mi / 10.2 km)
  • Howard Prairie Lake (16.1 mi / 26 km)
  • Lake of the Woods (28 mi / 45.1 km)
  • Bull Gap Lower Trailhead (7.1 mi / 11.5 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 home?
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 home accommodation in Ashland?
Houses are the most popular kind of holiday home in Ashland, according to our data. Even if you have a different vision in mind, Stayz has properties in many sizes and shapes. Explore our options to find your perfect match.
How much does it cost to rent a holiday home 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 Stayz holiday homes 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 Stayz 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 homes in Ashland?
Yes, there are. You'll find 59 holiday homes that welcome pets in Ashland on Stayz. Our furry friends need a break too, so simply use our search function for pet-friendly holiday homes to find a property where Spot can lap up the good times.
What are popular home amenities in Ashland?
Tennis, a barbecue grill and a firepit rank as the most popular home amenities in Ashland. Whether you're planning to travel alone, with your sweetheart or a group of best friends, Stayz will help you find a holiday home that matches your tastes with all the features you'll enjoy.
Are there large group holiday homes in Ashland?
Ashland has seven holiday homes 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 homes 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 homes 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 homes in Ashland?
Ashland has 12 two-bedroom holiday homes 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 Stayz.
Are there holiday homes with WiFi in Ashland?
Ashland has nine holiday homes 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 Stayz homes make it easy to go online.
How can I find holiday homes with air conditioning in Ashland?
Decide on your travel dates and then use our filters to look for holiday homes with ac in Ashland on Stayz. 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 home in Ashland?
The minimum age is generally 16, 18 or 21. It can differ between properties on Stayz, so check the rules of your preferred Ashland holiday home before booking.
How long can I rent a holiday home 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 Stayz 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.