Ashland, Oregon Vacation Rentals

Explore 34 rental homes and villas in Ashland, Oregon for your next vacation or business travel. With private vacation home rentals, enjoy a more personalized stay and a wide range of amenities such as Air Condition Homes, Pet-Friendly Homes and Best Affordable Homes. With a wide range of homes to offer, pricing can start as low as $72 per night with homes containing as many as 5 bedrooms and 5 bathrooms. However you're looking to experience your stay, Homes and Villas by Marriott has your next vacation home waiting.

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Ashland Overview
Nestled in the heart of Oregon's Rogue Valley, Ashland emerges as a picturesque enclave where cultural sophistication meets the wild beauty of the Siskiyou and Cascade mountain ranges. This gem of the Pacific Northwest is not just a feast for the eyes but also a sanctuary for the soul, offering an array of experiences that cater to every kind of traveler. At the heart of Ashland's cultural scene is the renowned Oregon Shakespeare Festival, a prestigious celebration of the Bard's work alongside modern masterpieces. This theatrical extravaganza, running from February to October, transforms the city into a vibrant stage, attracting enthusiasts from across the globe to revel in its artistic splendor. Beyond the allure of the stage, Ashland's artistic pulse beats strong with galleries, concerts, and lectures that ensure a constant stream of creative nourishment. Yet, the city's appeal extends far beyond its cultural offerings. Imagine waking up in a private home, a tranquil haven all your own, where you can sip your morning coffee in a sun-drenched garden or by a private pool—a common luxury in this idyllic destination. Many of these homes offer pet-friendly accommodations, ensuring that your furry companions can join in on the Ashland adventure. While Ashland may not boast oceanfront views, it compensates with the enchanting Lithia Park. This 93-acre wonderland invites you to meander through its serene walking paths, play a match on its tennis courts, or meditate in the tranquility of its Japanese gardens. The park is a cornerstone of Ashland's outdoor life, complemented by the myriad of trails and natural escapades that await in the surrounding mountains. The city's culinary landscape is a testament to its commitment to local and organic produce, with a variety of dining options that range from quaint cafes to gourmet restaurants. Each meal is an opportunity to taste the bounty of the Rogue Valley, a region also celebrated for its exquisite wines—a perfect pairing for any epicurean exploration. For those seeking rejuvenation, Ashland's spas and wellness centers offer a sanctuary for relaxation and renewal. The local shops and boutiques, meanwhile, provide a treasure trove of unique finds, from handcrafted goods to rare books, ensuring that every shopping experience is as distinctive as the city itself. Community spirit shines through in Ashland's weekly farmers' market and the myriad of festivals that dot the calendar, celebrating the city's love for film, food, and fellowship. These events are a vibrant expression of the local culture and provide a warm welcome to all who visit. Ashland, Oregon, is more than just a destination; it's an experience that seamlessly weaves together the threads of culture, nature, and indulgence. Whether you're drawn to the dramatic flair of the theater, the call of the wild, the allure of culinary delights, or the simple pleasure of a secluded poolside retreat, Ashland promises a stay that is as enriching as it is unforgettable.
Cultural Attractions in Ashland
Ashland, Oregon, nestled in the Rogue Valley and surrounded by the Siskiyou and Cascade mountain ranges, is a cultural oasis that offers a rich tapestry of arts, history, and local customs. This charming town is perhaps best known for the Oregon Shakespeare Festival, a world-renowned theatrical event that runs from February to October and features a mix of Shakespearean and contemporary theater productions. The festival's three theaters, including the outdoor Elizabethan Stage, become the heart of Ashland's cultural scene, drawing theater enthusiasts from around the globe. Beyond the plays, the festival also offers backstage tours, providing a glimpse into the magic of theater production and the history of this prestigious event. Art lovers will find a vibrant community in Ashland, with numerous galleries and studios showcasing the work of local and regional artists. The First Friday Art Walk is a monthly celebration where galleries open their doors for visitors to enjoy art, music, and wine while mingling with artists and fellow art aficionados. For those interested in history, the Ashland Historic Railroad Museum delves into the town's past, highlighting its connection to the railroads that once fueled its economy. The Southern Oregon University's Hannon Library houses the Schneider Museum of Art, which features rotating exhibitions of both historical and contemporary art, providing a window into the region's artistic evolution. Live music thrives in Ashland, with a variety of venues hosting performances ranging from classical to jazz to indie rock. The Ashland Armory and the Oregon Cabaret Theatre are just a couple of the spots where you can catch live shows in an intimate setting. Local customs are celebrated through Ashland's seasonal events, such as the A Taste of Ashland, which pairs local art with regional wines and gourmet food. The Ashland Independent Film Festival, held annually in April, showcases independent films and offers a platform for filmmakers to engage with audiences. Ashland's culinary scene complements its cultural offerings, with a focus on farm-to-table dining and an array of restaurants that highlight local ingredients. The town's farmers market is a weekly event where you can sample the region's produce and artisanal products, further connecting with the local culture. In Ashland, the blend of natural beauty, artistic expression, and historical charm creates a unique cultural experience that is both enriching and inspiring. It's a destination where the arts are not just observed but are an integral part of the daily fabric of the town, inviting visitors to immerse themselves fully in the local culture.
Kids IconFamily friendly activities in Ashland
Ashland, Oregon, is a charming destination that offers a delightful mix of cultural experiences, outdoor adventures, and educational opportunities that children will love. Begin your family journey at the ScienceWorks Hands-On Museum, where kids can engage in interactive exhibits that make learning about science and technology an absolute blast. From exploring the principles of physics to getting creative in the Da Vinci's Garage maker space, there's no shortage of fun and discovery. For a touch of outdoor magic, take the family to Lithia Park. This sprawling 93-acre park is the crown jewel of Ashland, with playgrounds for the little ones, duck ponds, and a Japanese garden that provides a serene setting for a family picnic. The park also offers easy trails that are perfect for a leisurely stroll or a more adventurous hike through the beautiful Oregon scenery. The Oregon Shakespeare Festival, although known for its appeal to adults, also caters to younger audiences with family-friendly productions and engaging workshops that introduce children to the world of theater. Check their schedule for performances that are suitable for kids, which can be a wonderful introduction to the arts. Ashland's seasonal events are also a hit with families. The Fourth of July parade is a colorful and festive celebration, while the Ashland Independent Film Festival often features films for children and families. During the winter, the Festival of Light kicks off the holiday season with a grand illumination of the town and a visit from Santa. For a unique educational experience, visit the North Mountain Park Nature Center. Kids can learn about local wildlife and plants through interactive displays and outdoor exploration. The center often hosts workshops and guided nature walks that are both fun and informative. Don't forget to indulge in some sweet treats at the local ice cream shops or enjoy a family meal at one of Ashland's many kid-friendly restaurants. With its welcoming atmosphere and variety of attractions, Ashland, Oregon, is a destination that promises memorable experiences for children and parents alike. Whether your family is looking to explore the great outdoors, dive into the world of science, or enjoy some theatrical magic, Ashland has something to offer for every young traveler.
Nature IconOutdoor activities in Ashland
Ashland, Oregon, nestled in the Rogue Valley and surrounded by the Siskiyou and Cascade mountain ranges, is a paradise for outdoor enthusiasts and nature lovers. This charming town is not only famous for its Oregon Shakespeare Festival but also for its stunning natural beauty and plethora of outdoor activities. Lithia Park is the crown jewel of Ashland, stretching over 93 acres. This beautifully landscaped park, designed by John McLaren (who also designed San Francisco's Golden Gate Park), offers serene walking paths, duck ponds, Japanese gardens, and a playground for children. The park is a perfect spot for a leisurely stroll, a peaceful picnic, or simply to enjoy the harmonious blend of nature and artistry. For those seeking a more vigorous outdoor experience, the surrounding mountains provide ample opportunities for hiking and mountain biking. The Pacific Crest Trail, a famous long-distance hiking path that stretches from Mexico to Canada, passes just a few miles from Ashland, offering breathtaking views and challenging terrain for serious hikers. The nearby Mount Ashland is a haven for winter sports enthusiasts. In the colder months, the mountain becomes a popular destination for skiing and snowboarding, with slopes suitable for all levels of experience. During the summer, the ski area's lifts give way to thrilling mountain biking trails. Ashland is also a gateway to the Rogue River, renowned for its world-class fishing, white-water rafting, and kayaking. Whether you're looking for a tranquil day of fly fishing or an adrenaline-pumping ride down the river's rapids, the Rogue River caters to all. For a more relaxed encounter with nature, Emigrant Lake County Recreation Area offers a tranquil setting for swimming, boating, and camping. The lake's calm waters are ideal for paddleboarding and kayaking, while the surrounding parkland has picnic areas and playgrounds for family-friendly fun. Ashland's proximity to the Cascade-Siskiyou National Monument ensures that nature lovers can explore a diverse ecosystem where the Cascade, Great Basin, and Siskiyou bioregions converge. This area is a hotspot for biodiversity and offers a unique landscape for hiking and wildlife observation. In Ashland, the connection with nature is intrinsic to the town's character. With its combination of cultural attractions and natural wonders, Ashland provides a perfect balance for those who appreciate the arts and the great outdoors in equal measure. Whether you're exploring the town's parks, hitting the trails, or enjoying the waterways, Ashland's natural beauty is sure to captivate and inspire.
Weather IconWeather in Ashland
Ashland, Oregon, nestled in the Rogue Valley, is graced with a climate that is generally mild and enjoyable throughout the year, making it a delightful destination for visitors. The city's weather is characterized by four distinct seasons, each offering its own unique appeal. Winter, from December to February, is the coolest time of the year, with average high temperatures ranging from the mid-40s to low 50s Fahrenheit (7-12°C). Nighttime lows often dip below freezing, and while snowfall in the city is relatively light, the surrounding mountains receive a good amount of snow, perfect for winter sports enthusiasts. Spring, from March to May, brings a refreshing change with temperatures gradually warming up to the 60s and 70s Fahrenheit (15-25°C). This season is marked by a mix of rain and sunshine, with April typically being the wettest month. The blooming flowers and greenery make this a beautiful time to explore Ashland's outdoor attractions, including Lithia Park. Summer, from June to August, is the warmest and driest season, with temperatures often reaching into the 80s and occasionally the 90s Fahrenheit (27-37°C). The low humidity during these months makes the heat more tolerable, and the long, sunny days are perfect for enjoying the Oregon Shakespeare Festival, which is a major draw for visitors. Autumn, from September to November, sees a gradual cooling with temperatures ranging from the high 70s to the low 50s Fahrenheit (25-10°C). This season is particularly pleasant, with less rainfall and the changing leaves providing a stunning backdrop for outdoor activities. The most popular weather conditions in Ashland are prevalent during the summer months, when the city is alive with cultural events and outdoor recreation. However, the climate is especially pleasant during the spring and fall, offering a comfortable balance between warmth and coolness, with fewer crowds and a chance to experience the city's natural beauty in a more tranquil setting. For those seeking the best overall weather, late spring and early fall are ideal times to visit Ashland. The temperatures are moderate, the rainfall is less frequent, and the natural scenery is at its most vibrant. Whether you're attending a play, hiking the local trails, or simply enjoying the town's charming atmosphere, Ashland's climate is sure to enhance your experience.
Transportation in Ashland
Ashland, Oregon, is a charming and picturesque town known for its vibrant arts scene, including the famous Oregon Shakespeare Festival. Nestled in the Rogue Valley and surrounded by breathtaking natural beauty, Ashland provides a variety of transportation options for visitors. Most travelers arrive in Ashland by car, as it is conveniently located along Interstate 5, which runs from California to Washington. For those flying in, the nearest airport is Rogue Valley International-Medford Airport, located about 15 miles north of Ashland in Medford. The airport offers a range of regional flights and is well-connected to larger hubs. From the airport, visitors can take a taxi, a shuttle service, or rent a car to reach Ashland. For those who prefer rail travel, Ashland is accessible via Amtrak's Coast Starlight route, which offers a scenic journey along the West Coast. The train station is located in nearby Klamath Falls, about an hour and a half drive away, and shuttle services are available to transport passengers to Ashland. Once in Ashland, getting around is quite convenient. The town itself is compact and very walkable, especially the downtown area where you'll find a variety of shops, restaurants, and theaters within easy walking distance. The presence of Southern Oregon University also contributes to the town's pedestrian-friendly atmosphere. For longer distances or to explore the surrounding areas, such as the beautiful Siskiyou Mountains or nearby wineries, having a car is beneficial. However, Ashland does have a public bus system, the Rogue Valley Transportation District (RVTD), which provides service within Ashland as well as to Medford and other neighboring communities. Biking is another popular mode of transportation in Ashland, with bike lanes and trails available for those who prefer to explore on two wheels. Bike rentals are available, and the mild climate makes cycling a pleasant option for much of the year. In summary, Ashland is a destination that is easily accessible by car, plane, or train, and once there, its walkable downtown and efficient public transportation make it easy to enjoy all that this cultural gem has to offer. Whether you're there to enjoy the arts, the outdoors, or the local cuisine, Ashland's transportation options cater to a variety of preferences and needs.