444+ Private Villas and Holiday Rentals in Ashland |
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  3. Medford
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Ashland Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Ashland

Discover more than 444 vacation rentals available in Ashland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Ashland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Ashland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Ashland. On average, places to stay near Ashland offer 543.36 ft², with nightly prices averaging US $275.

With Casai, finding and comparing holiday rentals in Ashland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Ashland

Type Count
Vacation Homes 209
Holiday Apartments 66
Cottages 30
Villas 3

Use these Quick Filters to Find a Holiday Rental in Ashland

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Ashland.

Weather in Ashland, OR

View the weather forecast for Ashland before booking your Ashland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Ashland, OR

Casai offers a large selection of top attractions around Ashland . Research things to do on your vacation before you visit Ashland.


Oregon Shakespeare Festival
Mount Ashland Ski Area
Southern Oregon University
Lithia Park
Historic Pinehurst Inn
Ashland Library
Oregon Cabaret Theatre
Howard Prairie Lake
Comer Ski Lift
Allen Elizabethan Theatre
Emigrant Lake
Thomas Theatre
North Mountain Park
Angus Bowmer Theatre
Schneider Museum of Art
Lithia Artisans Market
Hyatt Reservoir
Bull Gap Lower Trailhead
Windsor Ski Lift
Ariel Ski Lift

Other Places to Stay in Ashland, OR


Tashi Choling Buddhist Center 374 Properties
Ariel Ski Lift 367 Properties
Windsor Ski Lift 367 Properties
Comer Ski Lift 367 Properties
Mount Ashland Ski Area 367 Properties
Siskiyou-Hargadine Historic District 303 Properties
Ashland Library 301 Properties
North Mountain Park 301 Properties
Angus Bowmer Theatre 300 Properties
Skidmore Academy Historic District 272 Properties
Historic Downtown District 239 Properties
Historic Railroad District 47 Properties

Frequently Asked Questions About Ashland?

What are the top holiday rentals in Ashland?

With numerous options available in Ashland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Ashland:

How many holiday rentals have private pools in Ashland?

Discover a selection of holiday rentals with private pools near Ashland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Ashland are best for families?

If you're searching for a family-friendly holiday home in Ashland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Ashland:

How many Casai.nz holiday rentals are available in Ashland?

As of 2025, Casai boasts over 444 properties listed in the Ashland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Ashland.

Nearby Neighborhood (4) 
Neighborhood Property Count
Historic Downtown District Vacation Rentals in Medford, Oregon 239
Historic Railroad District Vacation Rentals in Medford, Oregon 47
Siskiyou-Hargadine Historic District Vacation Rentals in Medford, Oregon 303
Skidmore Academy Historic District Vacation Rentals in Medford, Oregon 272

People Also Ask

There are 444 Ashland, OR Holiday Rentals

Recently Booked Holiday Rentals in Ashland