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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.

Swank House -Downtown Suite- Pet Friendly - Ashland, OR
9.9 729 reviews

Swank House -Downtown Suite- Pet Friendly

apartment, Ashland
This apartment is located in Downtown Ashland, just steps away from the main street and within walking distance of shops, theaters, restaurants, and trails. The apartment has excellent user, location, and cleanliness ratings, making it a great choice for travelers.
The apartment has one bathroom and can accommodate up to two guests. Enjoy amenities like a private parking space, a seasonal patio, and a fully equipped kitchen with a fridge and microwave.
Cowslip's Upper Garden  Suite - Ashland, OR
10 8 reviews

Cowslip's Upper Garden Suite

apartment, Ashland
This Ashland apartment rental is located in a quiet residential neighborhood, three blocks from downtown Ashland and the Oregon Shakespeare Festival.
The one-bedroom, one-bathroom unit sleeps three with a private deck overlooking a shared garden, features a kitchen with a fridge, freezer, and microwave, and includes off-street parking.
Chalet "Fleur De Poirier" En Ashland - Ashland, OR
9.3 3 reviews

Chalet "Fleur De Poirier" En Ashland

chalet, Ashland
This Ashland, Oregon cabin, available for mid-term rental starting April 19th, offers a pet-friendly retreat with a private garden, Jacuzzi, and parking.
The one-bedroom, one-bathroom cottage sleeps two guests and includes a full kitchen (fridge, freezer), air conditioning, and internet access; further details on amenities and precise location are pending.
Swank Suites | King With Lux Tub - Ashland, OR
10 1 review

Swank Suites | King With Lux Tub

apartment, Ashland
This downtown Ashland apartment rental is one block from a grocery store and coffee shop, two blocks from an escape room, and within walking distance of the Oregon Shakespeare Festival and Lithia Park.
This 300-square-foot unit features one bedroom, two bathrooms, a king-size bed, a kitchenette with a microwave and mini-refrigerator, a private outdoor lounge, high-speed 5G internet, and accommodates two guests.

Best Ashland, OR vacation rentals with air conditioning

Swank Suites | King With Lux Tub - Ashland, OR
9.8 6 reviews

Swank Suites | King With Lux Tub

apartment, Ashland
This downtown Ashland apartment rental is ideally situated one block from a grocery store and coffee shops, within walking distance of the Plaza Center and the Oregon Shakespeare Festival.
The 400-square-foot unit features two bathrooms, a king-size bed, a kitchenette with a microwave and mini-refrigerator, a private balcony, high-speed internet, and accommodates two guests; nearby hiking trails and a common pavilion add convenience.
Lithia Springs Resort - Ashland, OR
9.2 1633 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.
Carter Lane Wee Casa - Ashland, OR
9.9 14 reviews

Carter Lane Wee Casa

cabin, Talent
The Wee Casa is a one-bedroom Talent, Oregon cabin located on a gated property with convenient access to Ashland and other local attractions.
This 400-square-foot cottage features a full kitchen, living area, bathroom with a large shower, private backyard, and two-car parking; it comfortably sleeps two guests and offers amenities such as air conditioning, internet, and a microwave.
Centrally Located Downtown Historic Home W/parking - Ashland, OR
9.7 46 reviews

Centrally Located Downtown Historic Home W/parking

apartment, 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.

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.

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.
Swank Boutique Suites | Double Shower - Ashland, OR
10 5 reviews

Swank Boutique Suites | Double Shower

apartment, Ashland
This Ashland Railroad District apartment rental is ideally located one block from a grocery store and coffee shop, two blocks from the Ashland Escape Room, and three blocks from downtown restaurants.
The 300-square-foot unit features a king-size bed, private outdoor lounge access, a shared pavilion with laundry, high-speed 5G internet, and accommodates two guests.
Swank Suites | King With Lux Tub - Ashland, OR
8.0 1 review

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.
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.

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.

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.
Cozy European Cottage 2 Bd + 1 Bath - Ashland, OR
9.0 2 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.
Luxury Ashland Mountain Escape: Pool, Hot Tub - Ashland, OR
9.7 30 reviews

Luxury Ashland Mountain Escape: Pool, Hot Tub

house, Ashland
The Jefferson Estate is located just outside of Ashland, offering stunning views of Grizzly Peak and a peaceful setting. The property has earned excellent ratings for location, cleanliness, and overall user experience.
This single-level home comfortably sleeps twelve guests with four bedrooms and four bathrooms. Enjoy the seasonal outdoor pool and hot tub, a stocked pond for fishing, a spacious lawn for games, and a fully equipped kitchen for preparing meals for a large group.
European Style Straw Bale Retreat - Ashland, OR
9.7 72 reviews

European Style Straw Bale Retreat

house, Ashland
This European-style straw bale home is situated on 14 wooded acres in Ashland, just minutes from the downtown area, offering a peaceful retreat while being close to the city's attractions. This rental has received excellent ratings for its cleanliness, location, and overall experience.
The apartment features an open floor plan with earthen floors and vaulted ceilings, spanning 1650 square feet. Enjoy amenities such as a kitchen with a fridge, microwave, and dishwasher, a terrace, a garden, a spa, parking, and a fireplace.

Best Ashland, OR vacation rentals with parking

Abbott's Cottages - Cardinal - Ashland, OR
9.8 251 reviews

Abbott's Cottages - Cardinal

bungalow, Ashland
Chateau Herb ~ Miranda Carriage House Apt - Ashland, OR
9.8 8 reviews

Chateau Herb ~ Miranda Carriage House Apt

apartment, Ashland
Executive Retreat Overlooking Ashland W/ Views - Ashland, OR
9.9 181 reviews

Executive Retreat Overlooking Ashland W/ Views

apartment, Ashland
Beautiful Ashland Flat - Ashland, OR
9.7 18 reviews

Beautiful Ashland Flat

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.

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

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.

The Aloha House - Hot Tub - Pool - Ashland, OR
9.9 157 reviews

The Aloha House - Hot Tub - Pool

apartment, Ashland

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.

Lithia Springs Resort - Ashland, OR
No 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.

Refurbished Barn On Acerage Just Outside Ashland - Ashland, OR
9.8 11 reviews

Refurbished Barn On Acerage Just Outside Ashland

apartment, Ashland
Gorgeous Italian Villa, Panoramic Views, Spa - Ashland, OR
10 14 reviews

Gorgeous Italian Villa, Panoramic Views, Spa

house, Talent
Chateau Herbe ~Miranda Carriage House Apartment - Ashland, OR
9.5 15 reviews

Chateau Herbe ~Miranda Carriage House Apartment

apartment, Ashland
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