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Ashland, OR vacation rentals
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Best Vacation rentals and Airbnb offers in Ashland, OR

Search Vacation Rentals near the Old Town in Ashland, OR

Choose a downtown Ashland, OR vacation rental for easy sightseeing. Compare the top centrally located properties and book your city stay with confidence.

Alley-by Loft: Smack Dab In The Middle Of Ashland!  Steps From Theaters & Lithia - Ashland, OR
9.6 5 reviews

Alley-by Loft: Smack Dab In The Middle Of Ashland! Steps From Theaters & Lithia

apartment, Ashland
This condo is located in Ashland's Historic Downtown District, a prime spot steps from restaurants and 0.5 miles from ScienceWorks Hands-On Museum, with easy access to North Mountain Park and the Cascade-Siskiyou National Monument.
This 1730 sq ft apartment offers 3 bedrooms, 2 bathrooms, accommodates 10 guests, and features a full kitchen with a fridge, microwave, and dishwasher, plus a rooftop patio with 360-degree town views.
230-downstairs-duplex-private Bathroom-mountain View - Ashland, OR
9.8 24 reviews

230-downstairs-duplex-private Bathroom-mountain View

apartment, Ashland
This 3-bedroom vacation home is located in Ashland's Historic Railroad District, just a 10-minute walk from the Oregon Shakespeare Festival and the Ashland Library. The house features a fully equipped kitchen, a garden, free Wi-Fi, and parking, making it ideal for families or groups of up to 6 guests.
Cowslip Historic Main House, Great For Gatherings! - Ashland, OR
10 24 reviews

Cowslip Historic Main House, Great For Gatherings!

house, Ashland
This charming apartment is just two blocks from Ashland's downtown, putting you within walking distance of restaurants, shops, and the Oregon Shakespeare Festival theater. It's also close to Lithia Park, a beautiful urban oasis with walking trails, gardens, and a picturesque creek. This apartment has excellent ratings for location, cleanliness, and user experience.
The four-bedroom, two-bathroom apartment comfortably sleeps up to eight guests. Enjoy a full kitchen, dining room, air conditioning, parking, and internet access.
Plaza North Suite 202 Sonoma - Ashland, OR
9.9 44 reviews

Plaza North Suite 202 Sonoma

apartment, Ashland
This Ashland condo, centrally located for easy access to Ashland's attractions and amenities, offers a convenient base for exploring the city and its surrounding areas.
This 1000-square-foot, one-bedroom unit features a king-size bed, modern kitchen with dishwasher, heated bathroom floors, a fireplace, and covered parking with EV charging, accommodating up to two guests.

Best Ashland, OR vacation rentals with air conditioning

Incredible 3 Bdrm On 5 Acres With Sauna And Creek - Ashland, OR
9.6 11 reviews

Incredible 3 Bdrm On 5 Acres With Sauna And Creek

apartment, Ashland
This three-bedroom Ashland apartment rental is situated in the Ashland farmlands, 1.5 miles from Emigrant Lake and a 12-minute drive from downtown Ashland.
The 3-bedroom, 2-bathroom home boasts a chef's kitchen, wood-fired sauna, event tent, trampoline, zip line, treehouse, and accommodates up to four guests, offering unique amenities alongside its proximity to Ashland's attractions.
The Ashland Social | Entire Estate - Ashland, OR
10 24 reviews

The Ashland Social | Entire Estate

house, Ashland
This luxurious four-bedroom Ashland house is located near the Oregon Shakespeare Festival, a short four-minute drive from Ashland Plaza and its restaurants.
The 4-bedroom, 4-bathroom home sleeps 12 guests with four king-sized beds and two queen-sized pull-out couches, boasting a private pool, hot tub, sauna, well-equipped gym with a Peloton bike, a chef's kitchen, and a separate studio kitchenette.
Cozy European Cottage 2 Bd + 1 Bath - Ashland, OR
9.3 3 reviews

Cozy European Cottage 2 Bd + 1 Bath

house, Ashland
This Ashland, Oregon house rental is conveniently located near various attractions, though precise distances aren't specified.
The 2-bedroom, 1-bathroom home sleeps 2 guests and boasts a fully equipped kitchen with appliances like a bread maker and air fryer, plus three TVs with Roku, a washer/dryer, and a dedicated workspace with Wi-Fi.
Blossom View Cottages: Luxurious 3 Bedroom + Den  Near Theaters, Downtown - Ashland, OR
9.6 85 reviews

Blossom View Cottages: Luxurious 3 Bedroom + Den Near Theaters, Downtown

apartment, Ashland
This charming 3-bedroom house is located in Ashland's Historic Railroad District, just a short walk from the Oregon Shakespeare Festival and Ashland Library. It has received excellent user ratings for its comfortable accommodations and convenient location.
The 1400 square foot house can comfortably sleep up to 10 guests and features a fully equipped kitchen, a spacious patio with a barbecue grill, a private spa, and parking. Enjoy the beautiful Ashland weather and relax in this comfortable home.

Frequently Asked Questions about vacation rentals in Ashland, OR

  • What are some interesting places to visit in or near Ashland, OR?

    Ashland is full of interesting places! You can't miss the Oregon Shakespeare Festival, of course. The Lithia Park is beautiful and offers great views of the city. If you're looking for something a little different, head to the Ashland Art Center or the Southern Oregon Historical Society Museum. And don't forget about the nearby Crater Lake National Park, about a 2-hour drive from Ashland.
  • What are the best Airbnb and vacation rentals in Ashland, OR?

  • Which walking or cycling routes are the best in Ashland, OR?

    The Bear Creek Greenway is a popular choice for both walking and cycling. It runs along Bear Creek and offers beautiful views of the surrounding mountains. For a more challenging ride, try the Emigrant Lake Loop, which takes you around Emigrant Lake and through the nearby forest. And if you're looking for a shorter walk, the Lithia Park loop is a great option.
  • What are the most popular Airbnbs in Ashland, OR?

  • What sports or outdoor activites can visitors enjoy in and around Ashland, OR?

    Ashland is a great place for outdoor activities. You can hike, bike, and fish in the surrounding forests and mountains. There's also great skiing and snowboarding at Mount Ashland in the winter. If you're looking for something more relaxed, you can go kayaking or paddleboarding on the Rogue River.
  • What are the best vacation rentals with a pool in Ashland, OR?

  • What other towns or cities can be easily accessed from Ashland, OR?

    You can easily reach Medford, about a 20-minute drive from Ashland. It's a larger city with more shopping and dining options. You can also visit Jacksonville, a historic gold-mining town about 15 minutes away. For a longer trip, you can head to Crater Lake National Park, about a 2-hour drive from Ashland.
  • What are the best rentals for families and kids in Ashland, OR?

  • What amenities are commonly available in vacation rentals in Ashland, OR?

    Most vacation rentals in Ashland will have basic amenities like a kitchen, bathroom, and bedrooms. Many also offer things like Wi-Fi, laundry facilities, and outdoor spaces. Some even have hot tubs or fireplaces. You can usually find rentals with specific amenities by searching online or contacting a local rental agency.
  • What are the best rentals or Airbnbs with a jacuzzi in Ashland, OR?

  • What time of year is best to rent a vacation rental Ashland, OR?

    The best time to visit Ashland depends on what you're looking for. The summer is the most popular time to visit, with warm weather and plenty of outdoor activities. If you're interested in the Oregon Shakespeare Festival, the summer is the time to go. Fall is also beautiful, with colorful leaves and cooler temperatures. Spring is a good time to visit if you want to avoid the crowds and enjoy the wildflowers.

Popular destinations

Best Vacation Rentals with Balconies in Ashland, OR

Enjoy your own private terrace with city skyline views at these vacation rentals in Ashland, OR.

Whimsy On B- 1 Block To Downtown Ashland - Ashland, OR
No reviews

Whimsy On B- 1 Block To Downtown Ashland

house, Ashland
This house in Ashland is located one block from downtown, a 5-minute walk to the Oregon Shakespeare Festival, and 400 yards from the Oregon Cabaret Theatre, with the Ashland Library 7 minutes away on foot and Lithia Park 0.4 miles distant.
This accommodation offers air conditioning, complimentary WiFi, a terrace, and free private parking, with no bachelor(ette) or similar parties permitted.
The Ashland Social | Main House - Ashland, OR
10 36 reviews

The Ashland Social | Main House

apartment, Ashland
This Ashland apartment is located just a short drive from the Oregon Shakespeare Festival and the Ashland Plaza, making it a convenient base for exploring the city's cultural attractions and vibrant downtown. The apartment has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This spacious 3,040 square foot home can comfortably accommodate up to 10 guests with its three bedrooms and four bathrooms. The apartment features a fully equipped kitchen, multiple dining areas, a private outdoor oasis with a hot tub, a well-equipped gym, and a sauna, offering everything you need for a relaxing and enjoyable stay.
Lithia Springs Resort - Ashland, OR
9.2 1607 reviews

Lithia Springs Resort

resort, Ashland
Lithia Springs Resort is located just 2.5 miles from downtown Ashland and the Oregon Shakespeare Festival, making it a convenient base for exploring the charming town and its renowned theater. The resort has received excellent ratings for its location, cleanliness, and overall guest experience.
The resort offers a variety of accommodations, including suites and bungalows. Each room features a soaking bathtub filled with natural mineral spring water, fireplaces, and flat-screen TVs. Guests can enjoy the resort's gardens, seasonal outdoor pool, hot tub, free hot breakfast, afternoon tea and cookies, and a fitness center.
Swank Suites | King With Lux Tub - Ashland, OR
9.4 3 reviews

Swank Suites | King With Lux Tub

apartment, Ashland
This downtown Ashland apartment, a block from a grocery store and coffee shop, offers easy walking access to the Plaza Center, Chozu Bath & Tea Gardens, and Ashland's other attractions.
This 300-square-foot unit features two bathrooms, a king-size bed, a kitchenette with a microwave and mini-refrigerator, and a private outdoor lounge; it comfortably sleeps two guests and provides high-speed 5G internet.

Neighborhoods and points of interest in Ashland, OR

Top Vacation Rentals for Families in Ashland, OR

Booking a family-oriented vacation rental in Ashland, OR keeps you close to top city attractions for a stress-free getaway.

Cozy European Cottage 2 Bd + 1 Bath - Ashland, OR
10 2 reviews

Cozy European Cottage 2 Bd + 1 Bath

cabin, Ashland
This Ashland, Oregon cabin rental is conveniently located within a 10-minute walk of Southern Oregon University, the Schneider Museum of Art, and ScienceWorks Hands-On Museum, and less than a mile from North Mountain Park and the Ashland Library.
This 800-square-foot lodge features two bedrooms, one bathroom, and accommodates two guests, offering a fully equipped kitchen, fireplace, private terrace, access to a fitness center, spa, and free Wi-Fi.
The Ashland Social | Guest Studio - Ashland, OR
10 27 reviews

The Ashland Social | Guest Studio

studio, Ashland
This studio apartment is conveniently located just a short walk from Ashland Plaza, putting you close to the city's center and its many attractions. The studio consistently receives excellent reviews from guests, highlighting its comfortable and convenient features.
The apartment offers a spacious king-size bed, perfect for couples or solo travelers. Guests can enjoy a kitchenette with a hot plate, fridge, microwave, and other appliances, allowing them to prepare light meals and snacks. The studio also provides fast Wi-Fi, ample street parking, and a private and quiet space for relaxation.
Historic Carriage House Close To Downtown Ashland - Ashland, OR
10 126 reviews

Historic Carriage House Close To Downtown Ashland

house, Ashland
This Ashland carriage house, built in 1884, is a 10-minute walk from downtown Ashland's shops and restaurants.
The one-bedroom, one-bathroom unit sleeps four, features a fully equipped kitchen with a new stove, dishwasher, and refrigerator, in-unit laundry, and private off-street parking.
Centrally Located Downtown Historic Home W/parking - Ashland, OR
9.7 49 reviews

Centrally Located Downtown Historic Home W/parking

house, Ashland
This Ashland, Oregon rental is centrally located, within walking distance of downtown, the Ashland theaters, and Lithia Park.
This three-bedroom, one-bathroom house, sleeping six, offers a fully equipped kitchen, air conditioning, parking, and Wi-Fi; built in 1887, it combines historic charm with modern amenities.

Best Ashland, OR vacation rentals with parking

Stroll-inn, Downtown Ashland - Ashland, OR
10 12 reviews

Stroll-inn, Downtown Ashland

apartment, Ashland
Château Herbe ~ Vienna Room - Ashland, OR
9.8 115 reviews

Château Herbe ~ Vienna Room

castle, Ashland
The Ashland Social | Main House - Ashland, OR
9.8 64 reviews

The Ashland Social | Main House

house, Ashland
Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment - Ashland, OR
9.2 7 reviews

Chateau Herbe ~ Rosalind Carriage House Beautiful 1 Bedroom Apartment

apartment, Ashland

Compare Luxury Vacation Rentals in Ashland, OR

Discover ultimate relaxation in a luxury Ashland, OR vacation rental, where comfort meets a central, prime location.

Come Stroll-inn In Downtown Ashland - Ashland, OR
No reviews

Come Stroll-inn In Downtown Ashland

apartment, Ashland

Our Favorite Pet-Friendly Vacation Rentals in Ashland, OR

Discover dog-friendly vacation rentals in Ashland, OR situated perfectly for city walks and nearby dog parks.

Artisan 3-bedroom House In Tranquil Ashland Perfect For Your Getaway - Ashland, OR
No reviews

Artisan 3-bedroom House In Tranquil Ashland Perfect For Your Getaway

apartment, Ashland
Abbott's Cottages- Egret - Ashland, OR
9.7 161 reviews

Abbott's Cottages- Egret

house, Ashland
Charming House Two Blocks From Downtown Ashland - Ashland, OR
9.6 12 reviews

Charming House Two Blocks From Downtown Ashland

apartment, Ashland
Paschal Winery - Dream 1 Cottage - Ashland, OR
9.0 2 reviews

Paschal Winery - Dream 1 Cottage

apartment, Talent

Explore Vacation Rentals with a Pool in Ashland, OR

Choose an Ashland, OR rental with a pool for a refreshing swim right in the heart of the city.

The Ashland Social | Main House - Ashland, OR
10 36 reviews

The Ashland Social | Main House

apartment, Ashland
The Ashland Social | Entire Estate - Ashland, OR
10 19 reviews

The Ashland Social | Entire Estate

apartment, Ashland
The Ashland Social | Guest Studio - Ashland, OR
10 27 reviews

The Ashland Social | Guest Studio

studio, Ashland
Lithia Springs Resort - Ashland, OR
9.2 1607 reviews

Lithia Springs Resort

resort, Ashland

Search Vacation Rentals with Jacuzzi in Ashland, OR

Unwind after a day of urban exploration with a private hot tub at your own vacation rental in Ashland, OR.

Historic Dunn Ranch Ashland Oregon. Sleeps 12 To 14 Great For Large Groups. - Ashland, OR
9.8 20 reviews

Historic Dunn Ranch Ashland Oregon. Sleeps 12 To 14 Great For Large Groups.

apartment, Ashland
Modern Design In Ashland For Families W Hot Tub - Ashland, OR
10 6 reviews

Modern Design In Ashland For Families W Hot Tub

apartment, Ashland
Chateau Herbe ~ Rosalind Carriage House 1bdr Apt - Ashland, OR
9.8 17 reviews

Chateau Herbe ~ Rosalind Carriage House 1bdr Apt

apartment, Ashland
Château Herbe ~ Florence Room - Ashland, OR
9.8 38 reviews

Château Herbe ~ Florence Room

castle, Ashland
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