Ashland holiday lettings

We found 294 holiday rentals — enter your dates for availability

Discover a selection of 132 homes, 51 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:10 Oct - 17 Oct
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Why visit Ashland

  • Stunning natural landscapes: Ashland boasts breathtaking scenery, including picturesque lakes and nearby mountains, perfect for outdoor enthusiasts.
  • Cultural experiences: Immerse yourself in the local culture by exploring charming streets and vibrant arts scenes.
  • Outdoor activities: Enjoy a range of adventures such as hiking, biking, and relaxing in urban parks.
  • Romantic settings: Stroll through beautiful gardens and enjoy scenic views, ideal for couples seeking a peaceful getaway.
  • Diverse accommodation options: Choose from charming cottages, stylish apartments, or private holiday homes for a comfortable stay.

Popular types of accommodation in Ashland

You’ve chosen Ashland for your next getaway, and now it’s time to find the perfect place to stay. Explore a variety of popular accommodation options, including houses, charming cottages, and stylish apartments. Our comprehensive rental listings in Ashland ensure you find the ideal rental property to suit your needs, providing transparency and peace of mind for your holiday.

  • Houses: The most sought-after accommodation in Ashland, offering spacious and comfortable living for families, couples, or groups.
  • Cottages: Charming and cosy, these quaint retreats provide a delightful stay, perfect for a peaceful getaway.
  • Apartments: Ideal for those seeking convenience, these self-contained units offer a home-like atmosphere while exploring the area.
  • Cabins: Rustic and inviting, cabins provide a unique experience, often nestled in nature, perfect for a relaxing stay.
  • Chalets: These alpine-style lodgings offer a blend of comfort and charm, ideal for a picturesque retreat.**

Top attractions in Ashland

Ashland is a delightful destination for those seeking outdoor adventures and scenic beauty. With its picturesque lakes, modern colleges, and urban parks, the area offers a variety of attractions for travellers looking to immerse themselves in nature and enjoy a beach experience. Whether you're hiking, exploring the local culture, or simply relaxing in the great outdoors, Ashland promises a memorable holiday for all visitors.

  • Southern Oregon University: This modern university offers a vibrant atmosphere, with beautiful campus grounds and a blend of academic and cultural events. Visitors can enjoy the lively city vibes and explore various art installations.
  • Lithia Park: A picturesque urban park featuring lush gardens, walking trails, and playgrounds, perfect for families. Enjoy outdoor activities amid its serene setting, ideal for picnics and leisurely strolls.
  • Howard Prairie Lake: A stunning lake surrounded by breathtaking scenery, perfect for a romantic getaway. Enjoy beach activities, fishing, and picturesque views that create a tranquil outdoor experience.

Things to do recommended for couples

For a romantic escape in Ashland, indulge in skiing at Mount Ashland Ski Area or take an adventurous ride on the Windsor Ski Lift. Don’t miss a delightful visit to Paschal Winery, just 3.1km away, where you can savour fine wines in an enchanting setting.

Things to do recommended for families

Your family will delight in the wellness vibes at Lithia & Driveway Fields, only 6.2km from Ashland. For adventure, visit the Rogue Valley Family Fun Center, 9.9km away, or unwind at the nearby Howard Prairie County Resort, offering relaxation for all ages.

Things to do recommended for groups

Groups visiting Ashland can immerse themselves in the vibrant performances at the Oregon Shakespeare Festival, browse local crafts at the Lithia Artisans Market, and embark on an adventurous hike along the Bull Gap Lower Trailhead, enjoying the area's stunning scenery and outdoor charm.

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate quite a bit. Moreover, opting for a longer stay often results in significant savings. To discover the ideal Vrbo property that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay in and around Ashland

Ashland, Oregon, is a charming destination perfect for outdoor enthusiasts and adventure seekers. Nestled in stunning scenery, this friendly city offers a variety of experiences, from romantic strolls to family outings. Nearby attractions provide ample opportunities for exploration, whether you're hiking in the picturesque mountains or enjoying local culture. Don't miss the Ashland Oregon Chamber for insights on the best places to visit and things to do in this delightful region.

  • Historic Downtown District: The Historic Downtown District in Ashland is a charming area that perfectly blends history with modern-day culture. Known for its romantic ambience, it's an excellent spot for families and outdoor enthusiasts alike. The district boasts various theatres, including the renowned Oregon Shakespeare Festival, and offers educational experiences through local museums. Nature lovers will appreciate the nearby lake and access to the stunning national and state parks, perfect for hiking and leisurely strolls. This vibrant neighbourhood is ideal for those looking to immerse themselves in Ashland's artistic and natural beauty.
  • Talent: Located a mere 3.1km from Ashland, the city of Talent is a hidden gem for those seeking adventure and picturesque scenery. This area is characterised by its outdoor recreational spaces, making it a favourite for hiking, cycling, and even skiing in the winter months. The local theatres provide a dose of culture, while the beautiful lakes and national parks nearby offer endless opportunities for exploration. Talent is a delightful destination for those wanting to indulge in nature while enjoying the charm of a small-town atmosphere.
  • Historic Railroad District: The Historic Railroad District, also in close proximity to Ashland, is a delightful neighbourhood that caters to families, couples, and outdoor adventurers. This area is steeped in history and features charming buildings that tell the story of the past. Visitors can explore local theatres and enjoy scenic hiking trails, while skiing at nearby resorts adds to the adventure. With a beautiful lake and access to magnificent national and state parks, this district is a fantastic spot for those seeking both excitement and relaxation in a picturesque setting.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 SunnyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighSlightly Low
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

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

If you're planning a trip with a group, family, pets, or seeking longer stays, it's important to filter your options according to your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Ashland with a group: Think about how many bedrooms you’ll require, as well as features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Ashland with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, as well as ensure access to suitable amenities like a private swimming pool. Additionally, it's wise to take into account your closeness to family-friendly attractions.
  • Taking your pets with you to Ashland: For many, a family holiday wouldn’t be the same without their four-legged companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Ashland: If you’re in search of holiday rentals with offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to include options like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up where you left off, or manage your travel arrangements. You can easily access the properties you've saved and booked, now organised under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • Paschal Winery (5 mi / 8.1 km)
  • StoneRiver Vineyards (7.5 mi / 12.1 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)
  • North Mountain Park (0.7 mi / 1.2 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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